Transfer window deep dive | The Football Boardroom

2 Sep 2026 · 1 h 1 min · 25 chapters

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In short

A transfer-window “deep dive” focused on Everton’s deadline-day turmoil, then broader analysis of why Premier League fees are rising and how different clubs manage risk, wages, and finances.

Guests/backgrounds

Henry (sports/football finance commentator; former chief executive experience implied) and H (co-host/analyst). They discuss clubs from a strategy/people/finances (SPF) lens.

Key claims

  • Everton’s window shows “worrying signals” in recruitment process and relationships: tension between owners/CEO Angus Kinnear and manager David Moyes, plus fan backlash.
  • Deadline-day deals were too risky: Balogun failed a medical; Everton left the centre-forward replacement late; Jack Grealish’s loan is framed as a long-injury-recovery risk.
  • Everton sold their best player, Ndai, despite saying they’d keep him, implying fans were “given something” (Grealish) to calm unrest.
  • Roma (also owned by the same group) is contrasted as more disciplined and manager-aligned; Everton is portrayed as second in the “pecking order.”

Notable examples

  • Everton: Balogun to Everton (pulled after medical); Ndai sold to Man City; Grealish loan from Man City.
  • Market context: Grealish £100m, Declan Rice £105m; Chelsea’s Enzo Fernandes £125m sale to Man City; Arsenal’s controlled spending; Chelsea/Villa framed as positive net spend.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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The Impact of Jack Grealish's Transfer

0:27 to 1:30

Discussing the significance of Jack Grealish's transfer and its implications for the market.

“And you are the perfect person to have opposite me because you started it.”

Tensions at Everton Football Club

1:30 to 3:05

Analyzing the discord between Everton fans, management, and the recent player sales.

“I've just sensed a sort of bit of trouble at Mill recently.”

Risks of Deadline Day Transfers

3:05 to 5:39

Examining the risks associated with last-minute transfer deals and Everton's strategic missteps.

“And remember, this comes a fortnight after the Everton CEO, Angus Kinnear, had given an interview with BBC Radio Merseyside in which he said, look, it was bitterly disappointing the way the season ended.”

Jack Grealish's Loan and Medical Concerns

5:39 to 8:01

Discussing the implications of Jack Grealish's loan deal and the medical issues surrounding it.

“OK, throw in the fact that this guy, we believe, failed a medical tells me that somebody in that hierarchy, somebody in the recruitment department hasn't done their homework early enough.”

Comparing Everton to Roma's Transfer Strategy

8:01 to 12:29

Contrasting Everton's transfer approach with that of Roma and the impact on fan perception.

“I understand other clubs wanted to buy the boy.”

Leadership Challenges at Everton

12:29 to 14:00

Identifying leadership challenges at Everton and potential strategies for resolution.

“He's sitting there getting his dream move to the Premier League, expecting to start Everton this weekend.”

Fan Reactions and Team Dynamics

14:00 to 16:54

Exploring the impact of fan sentiments and team relationships on club performance.

“Well, they've always, I mean, just the reaction of the fans.”

Transfer Market Analysis

16:54 to 19:53

A deep dive into the transfer market performances of different clubs.

“And the Everton fans' frustration must be when they look around and they see the type of money being lavished around by clubs, okay, clubs in the Champions League.”

Financial Strategies in Transfers

19:53 to 22:06

Understanding the financial implications and strategies behind player transfers.

“That feeds into their willingness to spend.”

Arsenal's Transfer Window Review

22:06 to 24:32

Analyzing Arsenal's transfer strategies and potential missed opportunities.

“There is a strategic backdrop, and I think Manchester United is a strategic explainer.”
Show all 25 chapters

Wage Discipline and Club Ambitions

24:32 to 28:00

Discussing the balance between wage discipline and club ambitions in transfers.

“but to actually recognise what we all saw last May, that there was a perceptible quality difference in the forward areas between Arsenal and PSG in the Champions League final.”

Arsenal's Transfer Strategy and Wages

28:00 to 29:59

Exploration of Arsenal's financial discipline in the transfer market.

“I also sense that Arsenal are very, very disciplined on wages.”

European Football's Financial Dynamics

30:00 to 31:32

Discussion on how taxation and financial regulations impact player transfers in Europe.

“And I think there's another very boring but very important variable, which is taxation.”

Chelsea's Successful Transfer Window

31:33 to 35:03

Analysis of Chelsea's transfer dealings and their impact on team performance.

“who's actually gone, he's a member of the 100 club double over following his move from Benfica to Chelsea and now from Chelsea to Manchester City.”

Enzo Fernandes' Transfer Dynamics

35:04 to 37:38

Insight into Chelsea's sale of Enzo Fernandes to Manchester City and its implications.

“In the case of Chelsea, I agree with you.”

Enzo Fernandes' Transfer Dynamics

39:52 to 41:04

Insight into Chelsea's sale of Enzo Fernandes to Manchester City and its implications.

“Your to-do list may feel endless with new tasks and lists can easily begin to overrun your life.”

Valuation Factors in Football Transfers

41:14 to 42:05

Final thoughts on how player valuation is affected by known factors and relationships.

“The only difference is he's Argentinian.”

Transfer Analysis: Chelsea and City

42:05 to 42:56

Learn about the financial dynamics of recent player transfers involving Chelsea and Manchester City.

“And we saw Reinders, Gonzalez and Rodrigo for about£170 million.”

Xabi Alonso's Tactical Decisions

42:56 to 43:54

Explore Xabi Alonso's strategic choices and how they impact Chelsea's lineup.

“And I think City have got themselves a very exciting midfield.”

Aston Villa's Player Departures

43:54 to 45:56

Discuss the reasons behind Aston Villa's player sales and Unai Emery's management.

“There's no way in the new structure that he got a phone call saying, sorry, mate, we didn't get your replacement.”

Unai Emery's Strategic Vision

45:56 to 49:58

Understand Unai Emery's approach to rebuilding Aston Villa amidst financial challenges.

“And in the case of Villa, I think it really is a situation here where every single one of those sales has a different factor driving it.”

Impact of Financial Fair Play on Transfers

49:58 to 53:10

Examine how Financial Fair Play regulations shape transfer decisions for clubs.

“I know his salary has gone up a lot since I left.”

Tottenham's Transfer Strategy Shift

53:10 to 56:01

Analyze Tottenham Hotspur's new transfer strategy under Roberto De Zerbi.

“I mean, there's so many different transfers to look at, but were you surprised, coming back to our old friends at Chelsea, that they took Mudrik on.”

Tottenham's Transfer Strategy Analysis

56:01 to 57:31

Discussing the changing transfer strategy of Tottenham and its implications.

“relationship between Roberto De Zerbi and Johan Langer as his sporting director.”

Player Performance and Expectations

57:31 to 59:07

Examining player performances and expectations under new management.

“They're allowing their management team, Johan and the chief executive, Vinay, to go and get the business done early and rebuild this team completely.”
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Transcript

Automatic transcript. May contain errors.

0:26The top 10 deals. deals were£100 million plus deal. And you are the perfect person to have opposite me because you started it. You started the 100 Club with Jack Grealish going, was it four or five years ago, going from Aston Villa to Manchester City. And then what do I also see last night watching you over your shoulder is images of Jack Grealish going back into Everton on loan.

0:58Henry:Yeah, you're quite right. I was pretty proud of that deal all those years ago. It was a British record and felt like a good price. And I probably wouldn't have predicted it would become a mainstream price in the transfer markets in the Premier League. And I think we should look at it as really a feature of a very interesting set of circumstances that seem to be developing at Everton Football Club. And I don't know what you felt. I've just sensed a sort of bit of trouble at Mill recently. You know my obsession with sort of strategy, people and the finances, SPF, to try and unpick what owners and executives are trying to do with their investments in a football club.

1:48Henry:And the P bit of that, the people bit of that, the key working relationships, manager, sporting director, owner, chief exec. I sense a bit of trouble. Am I imagining that? You're not imagining it at all. I mean, you've only got to look at social media. you've only got to look at the reaction of Everton fans. Obviously, at the weekend, singing that they were going to start a riot, if Harrison Armstrong, this very highly admired 19-year-old midfielder, was sold to Nottingham Forest for£40 million. Because where is the hope? Where is the future? If you're selling a player who is homegrown, born in West Derby, not great for David Moyes from a footballing perspective, as well as from the fans' emotional perspective.

2:32The Freakin, the Freakin group, the owners, as the fans were going freaking crazy over it, the Freakin group themselves, they sensibly pulled the plug when they saw the reaction. But the reaction again last night as you were sitting the oasis of calm on that sofa, the reaction around Finch Farm, the reaction on Merseyside from Everton fans to this transfer window, effectively leaving them with only one centre forward when the Balogun deal fell through and with Njai, their best player, being sold. And remember, this comes a fortnight after the Everton CEO, Angus Kinnear, had given an interview with BBC Radio Merseyside in which he said, look, it was bitterly disappointing the way the season ended.

3:20Everton didn't win any of their last seven games. So he was referring to that. But he also said it's important we retain players like Njai, who's now been sold for$65 million, which is probably quite short-priced in the current transfer market. So look, you've been in that situation as a chief executive. You understand this SPF as you see it. Do you sense some, there must be some tension, obviously between the club and the fans at the moment, but also between the club and a highly respected manager in David Moyes? Yeah, I don't think David took particularly kindly to his homework

3:59Henry:being scored as a bitterly disappointing. He made some reference, I think, to the fact that that was kind of news to him. so I definitely sense a little bit of trouble there and there's nothing like a kind of deadline day cock up and that's the most generous way to look at it to really pick at those key working relationships when things go well there's a queue of people in football clubs trying to take credit but when a signing falls over I mean I went into Sky at 10 o 'clock last night for the last hour of the window and in that hour up to Big Ben striking I was watching the on-off saga around the Balogun move to Everton and it's a really sorry look and you started by referring to Jack's loan and you've also referred to the Ndai departure if we take those in around I think There's some worrying, very worrying signals there that I think we should home in on.

5:04Henry:The fact that on the last day of the window, deadline day, you know my views that it is a very risky time to be doing business. It's fine doing odds and sods, loose ends, getting your squad players that you've all agreed weeks ago are going to leave the building off and on loan. That's a natural business to do right at the end. But when you haven't got a centre forward to replace a departed centre forward, Beto's gone and you leave that deal to the last day of the window, that's risky. OK, throw in the fact that this guy, we believe, failed a medical tells me that somebody in that hierarchy, somebody in the recruitment department hasn't done their homework early enough.

5:53Henry:and it's not to me a coincidence that, you know, let's be really frank about Jack coming back on loan. Jack hasn't played football other than a cameo in the Community Shield for City for over seven months. It was after a great couple of months when he arrived at Everton, everyone, me included, were thrilled to see him back starting football matches in the Premier League and really exciting Everton and the Everton fans. And I couldn't have been happier for him. But it was a very nasty injury. It was a disastrous injury for him because he was trying to get back in the frame for England. And the facts are that apart from City, sticking him on the pitch for a few minutes in the community shield, which seemed to be saying, come and get him.

6:43Henry:He's all right. I noticed he didn't get many minutes in the Premier League after that. I think that is pretty risky business I understand he had lots of clubs looking at him Henry and City are very firm on their financial requirements this is a boy making the best part of 300 grand a week in the final year of a six year contract and they're looking for clubs to say we'll pick up most of your wages on a guaranteed basis and then top up to get us all our money back on an appearance basis I'm guessing, I am guessing maybe 200 to 300 grand a week guaranteed and then another 100, maybe another 50 grand in appearance.

7:27Henry:So they get most of his wages back. That's what City would have wanted. Lots of people would have liked to take a nibble at Jack, but most of them would have said, we'll pay as we play. He presumably would have had another medical. yeah well he had one yesterday and um and again i don't like deadline day medicals i really don't because what happens is if it's like uh you know we've all we've all done it we all go and see the doctor it's like lawyers you get you get gray feedback you don't always get black and white feedback looks all right but bit iffy here bit iffy there and on deadline day the problem is with time pressure weighing heavily with a big gap if we don't do this deal in my personal experience standards get compromised risks get taken at the margin that you end up regretting later i hope and believe jack's fine i uh i've got no reason to doubt that he'll be fine but the facts are I think Jack's arrival as an injured player recovering as their targeted centre forward Balogun who has failed a medical to me two key signings on deadline day of players where there is an injury issue that compounds the risk and smacks to me of question marks about the process And the other feature of this that I don't like is, as you say, by common consensus, their player of the year, Ndai, last year, who they said they wanted to keep, nobody wants to sell their best player, ends up going to City.

9:09Henry:There was a bit of a tug of war. I understand other clubs wanted to buy the boy. He had a great season, looks an excellent prospect. But I think probably City being able to offer Jack as part of that deal helped them get Ndai. And this is the bit I don't like. Probably upped the ante, particularly after the interlude with the academy player you've referred to, where fans aren't just complaining. Fans are threatening to riot and an owner reverses an agreed sale. That's not an everyday occurrence in English football. Fans are unhappy all the time. But fans saying, sell that player and we're going to make your life misery.

9:50Henry:That's quite extreme. The owners reverse out of that H. And I think, and then they're thinking, Christ, we're going to sell Ndai our best player. We need to give the fans something they like. And I think that just probably shifted the balance to let's get Jack back. He's exciting. He's a fantastic fella. The fans like him. Maybe that mitigates some of the issues with the fans. I don't like any of those aspects to this overall puzzle. CP, take me into the boardroom and let's just see if we can see it from Kinnear and the board's perspective. With Balogun, was there an element of, he failed the medical, but actually, because they rushed it, as you say, it's on the last days, had 79 days to prepare for this.

10:34Obviously, there was a World Cup in the middle of it, which would obviously sort of delay things like that. But if it was just a niggle, couldn't they have done some deal, which actually then, whether it was a loan until January and then a sort of obligation to pay then if he played a certain amount of games?

10:55Henry:Look, I think that the point about the last minute aspect to this business for Everton is that when it goes wrong, you really do have limited room for manoeuvre. what actually happened was that they clearly had a problem with the medical i would argue in the conversations leading up to yesterday they should have known there was a risk of that at a minimum um they bounced on to trying to take xerxi out of manchester united you know on the last night of the window after a long time man united said no tammy abraham they had a look at okay so so and then when neither of those were feasible, they appear to have bounced back to, can we do Balogun on a different basis?

11:41Henry:And the good news for Everton was that they somehow persuaded Monaco to recut that deal. So we know they agreed. We don't know what those changes were. We don't even know whether it was a transfer or, as you suggest, whether they said, how about we loan him until January? And if he plays minutes, plays a certain number of games, we have to buy him on the same terms in January. That's the deal I would have done. OK, I certainly wouldn't have said, look, at 40 with an injury, we don't fancy. But at 30 with an injury, we do. For me, you're either injured or you're not. I don't think that goes to a price reduction.

12:17Henry:But we don't know. We also don't know whether they tried to modify the terms with the player in any way, shape or form. But what we do know is it was the player who pulled the plug on the deal. He didn't like the feeling. He's sitting there getting his dream move to the Premier League, expecting to start Everton this weekend. He's getting told by Everton's backroom staff, there's something here we don't fancy on the medical. He just didn't like the feeling. He pulled the plug. Either way, they're left high and dry in the centre forward department. And I think when you compare that, and this is something that must be starting to really become into focus with the Everton fans, who I know well.

12:58Henry:You compare to Roma, by common consensus, they've had a great window. Also owned by the Freakins. Also owned by the Freakins before they bought Everton. So this kind of multi-club model and question marks about where their priority lies. Well, all I would do is contrast the strategic approach at Roma, the approach to finances, the approach to relations with the manager at Roma to where we are with Everton. Gasparini, you know, it's quite clear that Chelsea really fancied a Roma star midfielder to replace Fernandes. Kone, again, highly regarded central midfield player. Gasparini, head coach at Roma, says, no thanks, this boy's not going anywhere.

13:40Henry:Freakins say, no problem, we're keeping him. Chelsea got told. So Everton, what you're saying, is Everton second in the pecking order? I think the Freakins are running the risk of giving that impression. and we both know there is no fan base where I think that's going to be less welcome than Everton Football Club. Well, they've always, I mean, just the reaction of the fans. I mean, the 1878 group who do so much good work for the atmosphere at the new stadium with banners and TIFOs and flags and all that, they say, they've just released a statement just saying, you know, they're not going to be contributing any more of that.

14:18You've got a mutinous support. you've got tensions with the coach, you've got absentee owners. What would you do if you were Kinnear?

14:27Henry:Well, the first thing is you need to make sure these day-to-day working relations are squared away. If there are any tensions with David Moyes and the sporting director, Nick, they need to be ironed out. The risk here is that when the criticism starts to fly, finger pointing kicks in and that can really turn a crack into a great big wide fissure. So that needs to be nipped in the bud. That is a job of leadership. That is absolutely the job for the chief executive. But the bigger issue I'm alluding to here is the relationship between the guys running the football club, Angus, Kinnear, Nick, the sporting director and David Moyes and ownership.

15:12Henry:And I think this sense that they're running a kind of two-speed economy here. Roma, six major signings, widely viewed in Italy as being bona fide title contenders, a manager who, when he says I'm keeping my best player, keeps him. And we compare that to Everton's business this window. It's a bit underwhelming. Two million quid of net spend. You know, they buy a league championship player as a marquee signing in the middle of midfield. They buy Norgard, ex-Brentford, ex-Arsenal,£7 million central midfield player. Seem to be overloading in the wing department with George and with Brannan and the swap deal with Palace.

15:55Henry:But overall, leaving a glaring hole at centre forward, everyone tells me they need and want a right back. It's an underwhelming£2 million net spend and crucially selling your best player from last season when you said you wouldn't. It adds up to a really, really underwhelming window that is bound to shine a light on whether ownership is as focused, as supportive, as committed and as ambitious as they seem to be for Roma. I think we have to watch this space, but there are telltale signs. And H, I think we should come back to this in due course and do a proper deep dive. This is, we are looking at some symptoms from this transfer window as to behaviour, as to the strategic plan, as to the people relationships and as to money.

16:48Henry:And I think that combination raises real question marks about where they are going with this club. I think we should come back to it. We definitely should. And the Everton fans' frustration must be when they look around and they see the type of money being lavished around by clubs, okay, clubs in the Champions League. But, I mean, let's go into those£400 million players. Why are there Anderson, Rodgers, Enzo and Barcola, obviously, to Everton's neighbours? Liverpool, why are we seeing such huge fees? Well, I think there's a couple of factors and I think we should maybe draw a contrast here. And we talked about Jack going for 100 million, followed by Declan Rice, 105 million not long after.

17:40Henry:And then I think if we add to the list of England internationals, Elliot Anderson and Morgan Rogers, I think there's a common theme there. Financial investors value companies, value investments as a combination of risk and return. Risk is a key variable that drives valuation It drives valuation in the stock market, in the bond market And it drives valuation in the transfer market And I would argue that a player who has played in the Premier League Multiple seasons with a high playing record I.e. a high percentage of minutes over the full season And so low injury risk with demonstrable success, culminating in regular caps for his country.

18:36Henry:That is about as low risk a transaction as you can do. Jack Grealish from Villa to City, Declan Rice from West Ham to Arsenal. And I think Elliot Anderson and Morgan Rogers are continuations of that trend. It doesn't get less risky or put another way as a financial investor age, it doesn't get more valuable than those sites of sorts of signings. Throw in across the whole of the market, continued upward, meaningful upward growth in revenues for the biggest clubs in Europe. Total transfer spending this window is three and a half billion pounds. It's no coincidence that total revenue for the biggest 20 clubs in Europe was up last year about 11 percent.

19:23Henry:And all the key revenue drivers in top club football are up. Meaningful growth in commercial income still. Really meaningful growth in match day income as these new owners in many cases are driving ticket pricing, driving expansion of capacity, even driving new stadia. and most important of all, continued growth in TV money. All adds up to revenues for the biggest clubs in Europe growing double digit. That feeds into their willingness to spend. But how much they spend, H, I think is fascinating. As I've said, Premier League to Premier League, England internationals who've absolutely demonstrated their quality outside the big six and get bought by the big six with their revenue advantage.

20:11Henry:Anyone can see what drives that. And then we see, interestingly, with Barcola coming out of PSG, a slightly different phenomenon. That is where the four biggest clubs in Europe, PSG, Bayern, Real and Barcelona. Fascinatingly for me, Henry, slightly bigger than the next six biggest clubs in Europe, which are our big six. There's the top ten, four and six. They're the biggest ten clubs in Europe by revenue. Interesting that those really mega European clubs, continental European clubs, with the exception of Diamandis to Real Madrid, we don't see quite the same appetite for spending 100 million dollars, euros or pounds, do we?

20:53I mean, it's fascinating. I mean, the sporting directors of those clubs and many of the clubs in Europe must look at the Premier League and think that's absolutely the Wild West. What is actually going on, throwing the money around. But it's interesting. I mean, I've been through so many of these transfer windows and there's so many sort of immediate sort of hot takes on it and people saying, oh, the Premier League is doing this or Europe's doing that or is it wages? Is it transfer fees? Is it agents? And try to look through what's actually more stained glass window than a sort of simple window to actually look cleanly through because it can be risky making generalizations.

21:32And to come back to your point about the big English clubs, three of our biggest clubs have not addressed issues which have been clear for for a while so just just take me through just maybe we should go through bit by bit on obviously Manchester United you covered superbly and it's interesting the word that you used austerity I now read um in a lot of the sort of takes on it but but take me through that because

21:58Henry:my industry media we tend to generalize a bit I agree and very very well said I would argue that In all those clubs, there is a contextual aspect to each transaction which should suggest to us to be wary of overgeneralisations. There is a strategic backdrop, and I think Manchester United is a strategic explainer. They are running what I called an austerity style regime and a good bet. And I like to relate these strategies to the data. The data shows that the top 10 transfers by value in this window were all done by the so-called big six. Man United had one deal in that list and it's number 10 in that list, which was a£70 million purchase of Belieber.

22:52Henry:At no point in the last 40 years would we have expected to see a ranking of transfers by English football clubs where Man United are number 10 in terms of the biggest deal in the window. That's significant. That tells me it is a strategy. They are not being sucked into these£100 million plus transactions of buying world leading stars, proven top international footballers. And that is a decision. It's a strategy to give its name. I would suggest that perhaps the next club on that list who have a perceptible strategy around the issue of finance and valuation are Arsenal. because we said on our show about Arsenal two months ago, given their phenomenal revenues they're now generating on the back of on-field success, which, by the way, has helped them grow their commercial and match day as well, but fundamentally massive improvements in their revenue, biggest revenue in the league.

23:58Henry:We haven't yet seen the 26-year-end figures. They're going to be, I think, probably setting a new English record for revenue with one of the richest families in the world as their owner, with an excellent management structure that allows for quick decision making, I thought they would make sure they're building on strength and add three marquee signings in defence midfield and in the forward line to take them to the next level. To compete not just with their rivals in the Premier League, where by common consensus they're already favourites to win the Premier League. but to actually recognise what we all saw last May, that there was a perceptible quality difference in the forward areas between Arsenal and PSG in the Champions League final.

24:49Henry:Brilliant squad addition with Konza. Excellent signing in Grimoireis out of Newcastle to strengthen depth in the midfield. By the way, the bench the other night when they played Villa was absolutely extraordinary. They had two world champions on there. Yeah, Eze, Konza, Bruno Guimaraes. Marino Zubamendi. An incredible bench, showing depth. But what I'm alluding to, H, was not depth. I was alluding to, was there a final piece of the puzzle to add quality? And the obvious comparison is to Liverpool. And Liverpool went and got Barcola. Do you think Arsenal, if they pushed London element, the club of Thierry Henry, do you think that they could have, they should have pushed more for Barcola?

25:36Henry:I can't see on the, listen, behind the scenes, the skills of recruitment, the skills of the sporting director, you know, getting ahead of the curve, building a relationship with the player's agent, having good lines into the selling club. You know, that's the job of recruiting. I can't imagine why on the face of it, side by side, Liverpool v Arsenal, that couldn't have been a fair fight. And you just got the sense, as we did with the Morgan Rodgers deal, that Arsenal just weren't going to play that game. Because Arsenal looked at Morgan Rodgers and thought, there's an 80 million player. They've briefed heavily.

26:17Henry:They thought it was 80. And when Chelsea got into the 116 level, we're not playing in that game. Is that sensible or a false economy? Look, I think if Arsenal, as much as anybody in the Premier League, can afford to be the winning bidder when you are competing for absolutely elite talent. And for whatever reason, the price of elite talent now has a one in front of it in the Premier League. Barcola's come out of the double European champions World Cup a player that was not satisfied by being a bench player at PSG for reasons when frankly the two players ahead in the queue are even more elite global superstars it was a player, we said on this show three months ago we'll leave this summer the perfect recipe not quite happy with his non-starting status at his club incredible pedigree on the world stage internationally and on the club stage and to me that was a Premier League elite signing and I thought Arsenal would be more competitive there so I'm scoring them eight and a half out of ten for the window as high as that yes I think the Konza Grimoraes signings are brilliant signings well priced but I sense that Arsenal have an approach to spending which is controlled.

27:43Henry:That Cronky and Cronky Senior, Cronky Junior and Berta, who's doing their bidding in the transfer market, they are disciplined. And here's the key word we didn't hear a lot of last night on the Deadline Show. We don't hear enough of when we talk about the transfer business. It's not the 100 million price. It's the wage side of the equation. I also sense that Arsenal are very, very disciplined on wages. And if that means they miss out on players where rivals are paying a little bit more or a lot more, so be it. And one person's, you know, prudent financial regime discipline is another person's lack of ambition.

28:23Henry:If you're an Arsenal fan, you decide. I see a really well-run club. I see an incredibly disciplined and tightly run club. But this window, I would have pushed the boat out, particularly given I got Trossard and Martinelli out of the building, that's half the funding required to go get Barcola. So that is a strange decision. There's a broader issue here. And again, we sort of try to jump to generalisations. But why don't the elite superstars of Vinicius Junior and Alvarez, players like that, come necessarily to Premier League football? Because the wages are here. We always say it's the best league in the world.

29:01Not many of the superstars are here. that Real Madrid, Kane elected to go to Bayern Munich. Why? Is there any particular reason? Because the wages must be commensurate.

29:11Henry:It's interesting. We talked about those four huge clubs, Real Barca, Bayern and PSG. With the exception of Jan Diamonde going to Real Madrid for, I think, 125. Bayern's biggest signings, about 50. Paris Saint-Germain, maybe a bit more, 60 or 70. Barcelona, I think Anthony Gordon was their highest-priced signing at 70. Isn't that fascinating? So the notion that these transfer fees are driven by the superior revenues of our big six may be true, relatively speaking, within the Premier League. But the four clubs in Europe with even bigger revenues than our big six aren't quite playing in that same marketplace or certainly without the frequency and volume of spending we see.

29:58Henry:I suspect that the wage side of the equation is quite important. And I think there's another very boring but very important variable, which is taxation. And all of these key European economies have different approaches to income tax, top rate taxation, etc. And let's face it, I think, you know, the United Kingdom has become a little bit less welcoming at the very top end on that side of the equation as well. in recent times. And it's no coincidence that agents would be looking at that and taking a view. We all know this great old Italian word. It's been around your and my whole lifetime. Netto.

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30:40Henry:You know, how much am I getting net of tax into my pay packet every week remains the prevailing priority of every footballer I've ever met and their agents. And so net pay after tax is a huge driver of where players want to go. And if I'm right, just finishing on Arsenal, that the perceptions out there, that they're a little bit more disciplined on the wage side of the equation, and they're in England where, you know, taxation is high now at the top end. I just wonder whether that explains that, why those Uber stars aren't beating a path to the Emirates. You mentioned Neto, which immediately brings to mind the great Ruud Hullett, former Chelsea player, former Newcastle manager.

31:32But from the Chelsea perspective, we see the transfer record now belonging to Enzo Fernandes, who's actually gone, he's a member of the 100 club double over following his move from Benfica to Chelsea and now from Chelsea to Manchester City. I mean, I think Chelsea have had a really good window. When you look at Morgan Rodgers, you look at Emi Martinez, a goalkeeper that you know well from Villa, it looks like, you know, Lacroix coming in to defence as well. You look at that front line they've got now with Rodgers, Gio Pedro and Cole Palmer. I mean, that's one of the best attacks in Europe, let alone in England.

32:16Henry:They clearly did decide that though they have Rhys James, who can play the dual pivot role with Kaysido when everyone's fit, though they have Lavia, a very highly regarded player. It's fair to say Lavia and James do have tricky injury records recently, but both of those can play that role. Everyone's forgetting because he's injured that Jordan Henderson can play that role. And don't forget, you know, they don't have European football. So I think they thought that's decent cover. But Xabi said, I'd like I'd like to strengthen. And we know they were rejected by Roma, but they seem to have identified Kamara as an excellent potential signing and they didn't get him.

33:02Henry:And that's just a bit of bad luck. I think the way Monaco were conducting their business on the last day of the window, trying to maybe get one or other out the door, that is regrettable. Chelsea have used some very strong language to describe Monaco's behaviour in that discussion. It is what it is. Had they done that, then this would have been a 10 out of 10 window for Chelsea. Coming from Chelsea, I think a lot of fans will say. I agree. I think all's fair in love and war. I look at the big picture here on, let's start with the numbers. You know, they've generated a net profit with huge volume, maybe 10 ins and outs, plus or minus, you know, 360 of spending, 400 of generation of revenue.

33:53Henry:They make a profit. Let's not forget that is the regime they're operating under with what I've called the UEFA ankle tag, them and Villa, both in the so-called settlement agreements where their every move is being scrutinised by UEFA. And for our audience's benefit, keeping it really simple, essentially what you buy, you have to have paid for with a sale, what you pay in wages, you have to have paid for with a wage reduction. So think of the agreement is a general direction of travel to improve your financials, i.e. to improve your profitability, to improve your sustainability, to improve your wage bill and improve your transfer balance.

34:39Henry:So it's no coincidence that when it all when all is said and done, when I look at that net spend league table, this window, the two teams in the Premier League with positive net spend, they made more money selling than they spent are Chelsea and Villa. So big tick for conducting their business, for meeting those financial regulatory inquirements. And in the case of Chelsea, we'll come to Villa. In the case of Chelsea, I agree with you. Meaningfully improving their line-up whilst balancing the books across a huge volume of business. I say, I nearly swore badly, very well done. I've been there. I've done it.

35:24Henry:The volume aspect of the transfer business is also underappreciated. Every deal is tricky. Every deal has its complexity. Every deal has the risk it doesn't complete. We've seen that with Everton already in this show. And Chelsea got a lot of stuff done. And we used a phrase on this show, didn't we, in the day after Liam Rosinia left the building. time for a mid-course correction and they have had a the strategy of this club on the management side hiring a proven winner at Alonso I think he's the best signing of the window by the way but signing some experience just look at what they did to their spine Martinez Henderson and Wellbeck goalie central midfield centre forward in toto about 10 million quid on those three players bloody brilliant business okay and I like what I'm seeing and I completely agree with you the sexy signing of Morgan Rodgers filling out a front three of Rodgers, Parma and João Pedro who looks to be the glow up of the summer I think that's the best three in the Premier League I think everybody would agree I think most people would say that is a much more exciting front three than Arsenal how did Arsenal let that happen that's what I'd be saying it's interesting and you mentioned the fact that they are very good at selling.

36:45They've been particularly good with Enzo Fernandes because if he goes for 125 million to Manchester City, I mean, those figures tend to rise when there's an auction. But Real Madrid showed pretty much towards the end of last season they weren't interested in bringing in Enzo Fernandes despite his very public flirting with Madrid. but if there's no auction, if there are no other bidders for Enzo Fernandes, how come they got£125 million out of Manchester City?

37:19Henry:It's a great question and I agree with your assessment, which is they are very good sellers. They obviously had to establish the thought in City's mind that they would happily keep Enzo if they didn't get their number. and I think City believed that and I think they would have kept Enzo if they hadn't got close to their number. I agree with you. I think it's a brilliant sale given the contextual factors would have led you to believe a lower figure would ultimately have been achieved. There was. The day him and Cucurella slagged management off back end of last season was the day I thought those two footballers would leave.

38:03Henry:Anyone else who's shown that kind of attitude at Chelsea has been out the door, including a few managers. So I thought he would leave. And when Real said they didn't want him and Maresca landed at City, it seemed to me that was the only place he was going to go. And I thought it would be a lot nearer the hundred than actually an up pricing on what they paid for him from Benfica and a new record. I think that's absolutely superb salesmanship by Chelsea Football Club. To get that number points to a club who get a lot of criticism off the park, and who, in my opinion, run their club a bit like you run an elite stock portfolio.

38:45Henry:You know, players are like securities. They're like commodities. They are bought and sold. But fair play, they're bought and sold for profit and balancing the book. So I think fair play. Is there an extra dynamic here? And again, I'm slightly sort of drifting into, against my argument, we're drifting into sort of generalisations, but that clubs are backing new managers. So Maresca comes in, he clearly knows Enzo Fernandes, they have a good working relationship from his time at Chelsea, so City back him on that. I think the City side of the Fernandes equation is a really good question. Yes, quite obviously the sort of marquee back Maresca signing, the fact the player is well known to him, the fact there's obviously a good relationship there.

39:35Henry:This goes to my earlier comments about valuation and how you achieve those really, really high numbers. The only difference between Enzo Fernandez and those. Starting or growing your own business can be intimidating and lonely at times. Your to-do list may feel endless with new tasks and lists can easily begin to overrun your life. So finding the right tool that not only helps you out, but simplifies everything as a built-in business partner can be a game changer. For millions of businesses, that tool is Shopify. Shopify is the commerce platform behind millions of businesses around the world and 10 % of all e-commerce in the U.S., from household names like Gymshark, Rare Beauty, and Heinz, to brands just getting started.

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40:57Henry:And start hearing... Sign up for your$1 per month trial today at shopify.com slash realm. Go to shopify.com slash realm. That's shopify.com slash realm. Four English hundred million pound club members I named Declan, Jack, Elliot Anderson and Morgan. The only difference is he's Argentinian. All other aspects apply. One, absolutely proven Premier League performer, absolutely proven international performer, two World Cup finals, a World Cup winner. And then adding that third ingredient of known to the manager, my metric, my way of thinking about valuation here, they are all risk mitigation factors that go to higher value.

41:50Henry:And alongside Elliot Anderson, an Anglo-Argentinian rebuilt central midfielder of starters, by the way, across the pair of them, about£240 million as the starters. And we saw Reinders, Gonzalez and Rodrigo for about£170 million. I'll leave Buardi on the side as a one for the future, big investment in the future type deal. But in out, Anderson and Fernandes, funded by those three very highly priced exits. Probably a cost to change there. 170 plays 240. 70 million quid to get England and Argentina starting central midfield pairing. I think that's bloody good business. I described it yesterday and I'll say it again.

42:41Henry:Sorry to repeat myself. I like win-wins. I like deals that both sides feel good about it. And I think Chelsea, frankly, are happy to be shot of Fernandes for lots of off-field reasons. And they're delighted to bank£125 million. And so they should be. And I think City have got themselves a very exciting midfield. And they genuinely look like, in terms of line-up, squad capability, the side that can run Arsenal closest right now. And the one interesting bit on Chelsea is, is Zabi, obviously, because we know he's in a more powerful position, perhaps, than some of his predecessors. He must have said last night at the 11th hour, when I was sitting on that sofa, H, in Sky Studio, watching that clock click down to 11 o 'clock, when the news came in that they couldn't get Kamara and they followed through on the Enzo deal.

43:37Henry:Zabby must have said, I'm all right with that. I'm all right with that. I can make this work with Lavia, with Jordan Henderson, with Rhys James, and we'll have a look and see how we go to January. We don't have European football. That's quite a lot of cover. There's no way in the new structure that he got a phone call saying, sorry, mate, we didn't get your replacement. That would have been, I believe, a grown-up discussion manager to ownership. And having seen some of the clips of Xabi Alonso controlling balls and pinging 40-yard passes in training at Cobham, maybe he could step in there. I mean, one of the players that you mentioned that they brought in to sort of get Chelsea given that spine is Emi Martinez.

44:22And we talk about managers being the central force in all this. Obviously, Unai Emery, a manager you know well at Aston Villa. It's one of those ones where everyone's looking at it. why is there almost not a file sale but why are there so many players six or seven of the players players presumably who you know and you bought into the club ollie watkins fair play to me he scored uh last night that they have left what is that and they all seem to be to have left for individual reasons i mean some of it's financial some of it's sporting ambition some of it's the club wanted to move them on so again coming back to the sort of general point about it's difficult necessarily or dangerous to generalise.

45:08But just looking back at your old club, a club you have huge affinity with, you know, a lot of the people there, huge affection for supporters, staff, club generally. What do you make of Aston Villa? And do you think that Unai Emery must look around going, I mean, he sounds very confident in interviews, but he must be a little bit frustrated to lose effectively his spine.

45:30Henry:I'm not so sure about that. And I agree with you that it is really dangerous to generalise in that particular case for sure. It is easy to slip into a narrative that they're being forced to sell all the best players because they've got FFP issues or even worse, you know, the manager would wish to keep all these players, but he's being told what to do by the suits. These sort of narratives swirl around football and they're rarely true. And in the case of Villa, I think it really is a situation here where every single one of those sales has a different factor driving it. The start point coming away from the sheer joy and glory of winning the Europa League.

46:22Henry:That's the start point. and the people, the strategy, the finances, SPF. So I think strategically, first of all, we absolutely all know that Unai now with Pep out the equation, Jürgen out the equation, really is the senior citizen, any way you want to look at it, the grown-up in Premier League managers today. Very, very, very powerful and influential in decision-making. He's earned the right at Villa to be a driver of strategy as opposed to the other extreme where he does what he's told. So the notion that he would just be told, we're getting rid of all your best players because we've got an FFP problem, take it.

47:09Henry:Utterly and complete fantasy land. This guy is a key player. And I think that when I look at the programme, start with finance. It's UEFA, the UEFA ankle tag analogy, the settlement agreement, the need. If you want to bring players in, you've got to sell players for at least the same amount of money. If you want to sign a player, then those wages have to be paid for by wage reductions. That's the financial framework. The people and strategy side of the equation is a manager who always wants to improve. so as night follows day coming out of that final if Unai wants to continue to improve and bring new players in he knew he had to sell players and that start point would have been the Morgan Rogers sale because the Morgan Rogers sale is one of those sales which says we've got a very ambitious player coming off the back of a incredible two years since being signed for very little money out of Middlesbrough, now a star player for England, hanging out with all his England colleagues, the sort of profile player who would like to move on on the right terms, significantly improve his salary.

48:23Henry:That deal looks to me to have been a well-constructed player, player agent, football club. If we can get absolutely top dollar, it helps deal with our need to make a meaningful dent in our FFP calculations, or more accurately, the new UEFA and Premier League squad cost rule calculations. So that was the start point. It didn't in one fell swoop fix those FFP related issues, but it made a huge dent in them. And I would describe that as an agreed consensus led strategy. Then we look at the other four. OK, and I do think it is undeniable that the five best players have left and they do form the spine of the team.

49:09Henry:But let's look at Martinez and Watkins. Those two players have been linked with moves for the last couple of years repeatedly. Several centre forwards have come into the building permanently or on loan. It's never been quite clear whether Oli was Unai's absolute nailed on starter at centre forward. He's always seen off those rivals. He's ended up being a record goal scorer and a club legend. OK, and lo and behold, interest comes in from Saudi for the player. Life changing, life changing, generational wealth changing opportunity in terms of his earning power. What does that mean? Three times as much as he's on?

49:52Henry:Yeah, I reckon you take a really good Premier League salary and Oli would have been on a really good Premier League. I know his salary has gone up a lot since I left. A lot, by which I mean maybe twice. But let's say he's in the mid-hundreds, seven, eight, nine million pounds a year paying 50, 55 % marginal tax rate. Maybe he's taking home four, five million pounds a year. These are my rough guesses. I think you can see, you know, with no tax to pay, with a much higher basic pay going offshore for three years to Saudi, he may be taking home three times that figure, maybe more to replace Benzema.

50:33Henry:That's generational wealth. And the point is, if that bid comes in and Villa say, not on your nelly, you're our star centre forward. We don't want you to go. You're not going anywhere. Maybe it plays differently. But what I read, and I'm only seeing what I read, was not at that value. With the right value, we would consider it. And I think from that moment, the cat's out the bag. Ollie's going. They've shown a willingness, if the price is right, to sell a 30-year-old who they've had brilliant service from. and they've shown the football has been allowed to smell a fantastic opportunity to look after his children, their children and their children with generational wealth and seems willing to give up, you know, let's face it, the glory and the excitement of playing in the big five leagues in Europe and go to Saudi and get rich.

51:22Henry:Uri Tielemans had a clause, Man U lifted it. Do I suspect Villa deeply regret the fact he had a clause in the 30 millions? I think so. No way Uno would have wanted to lose that player, but somebody gave him a clause and United lifted it. Good business. And Esri Konza, he's the other one that got away. But that story is as old as the Hills, Henry. Another player has done brilliantly for the club over the long run. League champions come in. He's a London boy, probably a significant improvement to his wages. And it's really tough to hold a player in those circumstances. That's always been true. And it's about can you get a decent price?

52:02Henry:And it turns out that over 50 million quid for a near 29 year old centre backs, a very good price. Not a player they would have wanted to lose. But once Arsenal were in for him, they lose him. So in total, I think Unai is backing himself here with one crucial objective. Let's get our age profile down. Let's get our wage profile down. Let's try and once and for all be rid of these FFP SCR shackles, drive the average wage down. And Unai backs himself to replace like for like, quality with quality. The jury's out because for the first time, it is a bona fide new Unai recruited team. And two good kids from the academy in Hemmings and Maggio.

52:50I mean, Hemmings, impressing. and Madjo in that first game. He had four chances and took the most difficult one. So a little bit of homegrown prospect. I know you were very supportive of the academy during your time there. We need to look at the bottom of the table and look at Tottenham Hotspur, who have spent a huge amount. Well, it's all performance-related, CP. You keep telling me that. Yeah. Were you surprised? I mean, there's so many different transfers to look at, but were you surprised, coming back to our old friends at Chelsea, that they took Mudrik on. And is this just another reflection on managers, strong managers, almost being empowered by their clubs?

53:29Because De Zerbe kept spurs up, got this transfer window, knows Mudrik from their days at Schachter. I've interviewed Mudrik. I mean, he's quite an interesting, complicated, very intelligent character. But would you as a chief executive have been happy to take on that sort of loan with a player who does, let's be fair, come with a bit of baggage and he's not played for two years, partly because of the doping ban.

53:54Henry:I think it's a rounding error across a staggering window for Tottenham Hotspur. I think alone, I don't know what the terms are. There'll definitely be a performance element to it in terms of pay more if he plays more. If he turns out to rediscover the player that, by the way, Chelsea and Spurs went head-to-head for, Chelsea probably win that equation because there is no option or obligation to buy and Chelsea get him back and if Spurs rehabilitate him, brilliant for their trading model. But I think we need to focus on Tottenham on, to me, the big picture issue here is rarely do you see a profound change of strategy and a profound change to the management of finance when ownership doesn't change.

54:47Henry:and Joe Lewis and his family have owned this club for a very long time and frankly, you know, it was crystal clear that when Daniel Levy was running the club for them, you know, he was barely asking them if they would, you know, expense, you know, his taxi fares to go and buy footballers. At no point was the club asking ownership to inject large amounts of money. He ran the club balancing the transfer equation, a very tight ship on wages and delivered by the way the best stadium in europe with again virtually no money required by the best training ground magnificent training so so that was a no money in make it more valuable and cut your cloth strategy for the best part of 30 years overseen for the owners by by daniel as a co-owner but fundamentally managing the day-to-day and it's almost unbelievable that since Daniel left, that ownership group appear to have said to Tottenham's management team, let Roberto have what he wants.

55:54Henry:Don't mess about. He can identify the players he thinks make sense working closely. It's quite clear there's a very close working relationship between Roberto De Zerbi and Johan Langer as his sporting director. Empowered, Get Roberto the player he wants is Johan go and execute the business and don't mess about. You know, if you're up in competition, don't be frightened to win the auction on the transfer side of the equation. And obviously the equally, I would argue, more important part of getting deals done, be willing to pay the right wages to get top players. And that is the story of Tottenham's window.

56:35Henry:A complete change of heart. Do I think Spurs fans give a damn that they've spent 300 million quid net? I think about 170 when the owners haven't spent very much, if any, at all for 30 years. No, they don't. You know, could they could I with maybe a slightly more disciplined approach to purse strings have taken, I don't know, 50 million off that total spending? Maybe, but let's be clear. If this strategy works, then and by that, I mean Tottenham finishing the top five this year and are back in the Champions League. No one will be quibbling about whether it was 300 spent or 250 spent. Nobody, even Joe Lewis.

57:16Henry:And for me, I think it's a welcome change of strategy for a brilliant club. What is the point of having the finest stadium any of us have ever sat in and not having a team fit to grace it? They are backing this fella, De Zerbi. They're allowing their management team, Johan and the chief executive, Vinay, to go and get the business done early and rebuild this team completely. And I look to you, H, to explain. I can see strategy and finance there. Big ticks, if it works. But if, seems to me, to centre on issues around blending new players quickly and changing the culture. That seems to me to be Deserby's challenge.

58:02Henry:What do you think? I just really liked Zerbe and I think if the players respond to him Tonali didn't have the best game the other day Newcastle were terrific we must congratulate them they lost three big players brought in a relatively unknown manager and he's getting the best out of Alanga and Wissler as Spurs fans it's only two games H absolutely it's only two games and that's the point coming back to Spurs Tonali will absolutely I'm sure deliver he was almost a member of your famous 100 million club. So, look, they bought some interesting players. Savio, I mean, we talk about City, Chelsea being good sellers.

58:42City did good business there with Savinho, who is now Savio. Mudrik will see. I still think they need a centre-forward. Marmouche can deliver, but he's almost a support striker. But, you know, they bought some experienced players in the back, Andy Robertson, and SC players like that. So they have got, I think they've, they've done pretty well and they've got a good manager and if they respond to him then Spurs will be fine

From the publisher

In the wake of another record-busting transfer window, Christian and Henry pore over the big deals and pick apart the phenomena driving the market forces.

Who are the main winners and losers? What’s the recipe for a £100m deal? And why are so many of these transfers being done between Premier League clubs?

Email in via: getintouch@thefootballboardroom.co.uk 

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