Mourinho's Benfica vs Real Madrid (Again), Qarabag’s Cinderella Run, and Knockout Playoff Chaos: European Nights 02/17/26

0:00You're listening to the Men in Blazers media network, suboptimal radio. Have Jose Mourinho or Real Madrid ever recovered from his time there? Real Madrid, yes. Jose Mourinho, no. Is Azerbaijan the next European footballing superpower? Probably not, Rog, but never say never. Can just one more managerial firing fix Nottingham Forest forever? Not one, no. Not one. But two. Two, maybe. Five, maybe. Maybe the next guy after this guy. It's the round of 32 in the Champions League, the Europa League, and of course your beloved Conference League. So let's get it to the football. No, here comes to me. No!

0:41No!

0:48Are you ready for some football? It's Rog and you're listening to European Night. That's the dulcet tune of Nuno Matos on the goal call on Portuguese radio, having a Benfica-gasm as the Lisbon club defeated perpetual Champions League winners Real Madrid in the dying minutes of your big gold league phase to advance to the knockout rounds, where they will face, checks notes, Real Madrid again. It wasn't just a goal, it was in the 98th minute, and oh yeah, it was scored by the goalkeeper. And joining me as we go deep on this moment, the impending rematch and the sights and sounds and tastes of European football, I'm joined by a gent, Not to be confused with a lad of the same name whose dad stole his chicken nuggies at the Wolves game.

1:37As far as I know, he's working with a full deck of chicken nuggs. It's Mr. Rory Smith. How are you doing, Rog? I'm ready to go. All European on your a**hole. We want to look ahead to this tie, which puts Jose Mourinho against his former club, Real Madrid. But first, let's recap how we got there. Benfica, leading 3-2, wasn't enough to advance in the next round based on all the other results. but then former Real Madrid and Chelsea and Tottenham and Manchester United icon Jose Mourinho. He didn't seem to know that. He sent on a defender with his last substitution. Then the murmurs came from the bench.

2:12The gesticulating. Suddenly, Ukrainian goalkeeper Anatoly Trubin moved up for a last gas-free kick. 98th minute. Hail Mary. And it went in. And Benfica went into the top 24. Cue the only mildly obscene Jose Mourinho celebration and gyrations.

2:36I want to give huge thanks to Bank of America, Official Bank of US Soccer and the FIFA World Cup 2026 for supporting the Men in Blazers media network. Discover what's possible in sports and in life. What would you like the power to do? Ro, can you describe for us the full body tingle at this moment? It was a genuinely extraordinary conclusion to the big gulp group phase, the flyleaf table, as I like to call it, Rog. How often do you see a goalkeeper score, Rog? I've seen it happen, I think, twice before. They're incredibly rare moments for it to happen then when all of the eyes of Europe had switched onto that game in Lisbon because everything else had finished, and the goalkeeper gets a goal to seal it.

3:18The latter stages of the Champions League always produce these memorable moments, Rog, but they're going to have to really go some to beat that one this season. Yeah, in a plot twist, so pat and cute. The football script writers honestly will be accused of being a little bit too on the nose. Benfica then proceeded to draw Real Madrid in the knockout rounds. Benfica, in a delightful piece of shithousery, posted a picture of the team celebrating Trubin's late goal in the tunnel leading to the field. When Real Madrid arrived, that's what they'll be looking at. Mourinho's revenge extended, essentially.

3:52the scalding one, of course managed Real Madrid from 2010 to 2013, it was an incredible time for Spanish football a time of peak, feisty I think it's a kind word, rivalry with Pep Guardiola's all conquering ticky-tack of Barcelona and he turned it into scorching levels he won a Clasico Copa del Rey in 2011, the league title in 2012 but really the enduring memory of the time there was the, just an awful moment in a ruck in which he poked the eye of the late Barcelona coach Tito Villanova in the 2011 Spanish Supercopa during a touchline brouhaha, which was at the time just so Mourinho. It was shocking, but it didn't surprise anybody.

4:37And Real Madrid's steady but unheralded full-back during that time, a gent 20 years Mourinho's junior, Alvaro Albaloa, nicknamed El Espartano, the Spartan. His Instagram bio reads, no retreat, no surrender, that is Spartan law. Takes it very seriously. He was essentially a dutiful soldier back then, staying faithful to Mourinho, even after the dressing room atmosphere poisoned and the club spat Mourinho out like so many before and after. Shortly before we retired, Albaloa said, quote, I try to be as Mourinho Easter as possible. It's not hard to see how Albaloa climbed the rank swiftly, from Real Madrid TV pundit to club ambassador, to youth team coach, to interim manager after just six months with the reserves.

5:22Largely because he's willing to most forcefully parrot any conspiracy theories against the club. A tried and true Mourinho trick, us versus them. So Rory, what influence, if any, of the Mourinho era is left in that Madrid locker room? Are they going back to that type of siege mentality in some ways with double A as the interim help? I think there's a little bit of Mourinho in Arbeloa. He said when he got the job replacing his friend Xabi Alonso, he said that he wasn't going to be a Mourinho tribute act, that it wouldn't work if he just thought, what would Mourinho do in any given situation? He was his own man.

5:58He made a point of heaping praise on Mourinho, which he obviously genuinely admires him, but he didn't want to just be a caricature of Mourinho. He wasn't here to play Jose Mourinho. I think the influence is much more intangible. It's much more indirect. It strikes me you could easily build a case that Real Madrid before Mourinho doesn't feel as conspiratorial, doesn't feel as determined that the world is arrayed against them, doesn't have this kind of tendency to invoke conflict with almost everybody around it, whether that's Barcelona or UEFA or referees or whoever it might be. I think some of that is related to the kind of changes in the world that we all live in, Rog, that go way beyond football.

6:42I think part of it is Florentino Perez, the president of Real Madrid. I think that's very much how he sees the world. But it also feels very Mourinho. It feels very much like he went in to Real Madrid as the superstar coach, the Galactico manager, and just left the club with a little bit of his DNA. And these are the tricks that Mourinho has always played. and I don't mean that kind of insultingly. Mourinho, one of his strong suits as a manager is to make a club, make a squad feel as though it's them against the world. Everyone's out to get us. We are the underdog. We are the team that they don't want to win.

7:18And you look around and think, well, Jose, you're Chelsea or Jose, you're Inter Milan or you're Real Madrid. These are establishment clubs with huge amounts of money. But Mourinho's always been very good at forging that siege mentality, forging that sense of we have to kind of dig deeper, fight more to get what we want. And I think he somehow left that in Real Madrid, the most establishment club of all. It may well have happened anyway, but I just wonder whether Mourinho's presence made it faster and deeper that it kind of permeated the Real Madrid psyche. Yeah, I mean, Mourinho has gone on and since leaving Real Madrid, his tactics do seem to be about run by the constant evolution of football, probably for him the pesky constant evolution of football tactics, went back to England with Chelsea.

8:07Certainly been slumping down the list of prestigious clubs on the continent that will take him without a league title since. There's the Europa League trophy won with Manchester United, the Conference League, the world's most beloved trophy, TM, with Roma in 2022. But there's the inexorable feel of a man past his prime, most recently tucked away in Turkey with Fenerbahce, now back in his native Portugal with Benfica, the games with Real Madrid do scream and stand out because we have not seen Mourinho back on the international stage hogging the headlines, hogging the spotlight, almost like it's 2006 again.

8:44Raw, Mourinho, has he recovered from his Real Madrid stint? Did that shatter his illusion almost, dent his sense of self internally, if not the projection externally from his own ego? or is this just a case of the sands of time eventually burying us all one grain at a time? There's definitely an element of that, that Mourinho, like all managers, as he's got older, has become almost more, well, maybe this is true of all of us, Rog, you get more set in your ways. You get more kind of... I thought you were going to say, I get more David Moyes the older I get. That's what you're saying. I suppose as you get older, you do become a little bit more kind of convinced that this is the way I do things and that's not going to change.

9:23That is just me doing an impression of my dad. but I think it's probably true of all of us. There is this thing with managers where they do tend towards becoming caricatures of themselves. So it sounds a bit of a generalisation but I always think that managers after a certain point become more determined to win the way they say they want to win than just to win. That proving the point is more important than the results. Arsene Wenger is the great example of this. Late era Arsene Wenger just refused to change because he stood for something and if he won any other way, it would almost have been a personal defeat because it would have suggested that the ideals he'd always had weren't right.

10:04I think that is true to an extent of Mourinho. You wonder to an extent whether he's refused to indulge the positional play game, that Guardiola style of football a little bit, because that would be admitting that Pep had a better idea than him and he's just not prepared to do that. But I think the big thing with Real Madrid and the impact it left on Jose, it almost took him to a level that he's not been able to quite recover from not just the pressure and the stress of being at Real Madrid of being at Real Madrid at the time when Pep Guardiola's Barcelona were your rivals but all of the the conspiracy the conspiracy the controversy the need to cultivate controversy to try and gain an edge the wars of words in the press the endless press conference barbs all of the spite and the malice and the fury and the anger and the the The kind of poison of that rivalry seemed to seep into Mourinho a little bit.

10:58There's a little bit of a misconception of what Mourinho was like when he first arrived in England. I think Jose Mourinho was quite fun when he arrived in England. There was a little bit of a glint in his eye when he said the things that made him such a character, that made him so beloved of the media. After Madrid, the glint in the eye disappeared. He believed the kind of caricature that he had created of himself. and I think it's not unrelated that he's not quite been able to recapture the heights of Chelsea and Inter Milan, the two greatest kind of roles in his career, that he does feel like a man who was in just some small way slightly broken.

11:36Maybe not broken, but has never fully recovered because he had to give so much of himself to Real Madrid that there wasn't all that much left. God, I know, I know, dear listeners, many of you are no doubt screaming at your pod radios, saying this isn't the Mourinho derby. No, everyone should be thinking about the 1962 European Cup final, when two goals in three minutes from Eusebio, that legendary Portuguese striker, a pearl known as the Black Panther, still a 5-3 victory for Benfica over Real Madrid, giving them a second consecutive European Cup. Others undoubtedly think about the time these two teams met in the 1965 quarterfinals.

12:17Yeah, Benfica advancing then 6-0 on aggregate. Any way you slice it, Benfica have a sneakily good record against Real Madrid. Three wins to one, especially since that 1962 meeting was the last time Benfica won the whole enchilada. Real Madrid have gone on to win it a record 15 times. This 2026 edition, there's no Eusebio knocking around, unfortunately, for Benfica. is this where the fine record meets its demise? What kind of game do we expect as Mourinho pull one off over his old launch pad? Logically, yeah, I think so. It feels like he and Benfica had their moment with that Troubin goal. It's really hard to see them picking away past even a flawed Madrid.

12:59Abelho has not had a brilliant start at Madrid in a knockout game over two legs. This Benfica is different to kind of what we think of Benfica as being in the last five or ten years. There's no João Neves who's about to take the world by storm. There's no really young talent who is going to kind of grasp this Benfica team and carry them through. They've gone for a much more win-now kind of approach. They've spent quite heavily on players in their early to mid-twenties. There's no teenagers particularly in the side. We saw it a few weeks ago, have the quality to beat Madrid over one leg. I think over two, it's pretty unlikely, to be perfectly honest, especially with the second leg in the Bernabeu.

13:38You'd expect Madrid's ability, their talent, the level of Galactico stardust they have to tell eventually. But, I mean, there won't be a manager in the world who's more motivated for a game than Jose Mourinho for the two legs of this one. So you never know. But I think Benfica have already had their moment this season. Remember the old John Oliver mantra, spite is the rocket fuel of human motivation. I do believe this one is actually tied at the end of two legs. That's dispenser the football, yeah? Let's plop a table in the middle of the Bernabeu. Make Mourinho. Oh, and Arbolowa. Just have a Russian slap fight to find out who progresses.

14:15Who wouldn't want that? But first, Tuesday, February 17th, 3pm Eastern. We're off to Lisbon for the first leg. And even before that, we're off to meet the Azerbaijani Alex Ferguson. Yeah, after this quick break.

14:31Cast you from the turn!

14:37Amazing! That, dear listener, is the sound of silence. Not the Paul Simon kind. It's in fact a shock Benfica home crowd collectively, quietly, surrender Copa Ringo. I don't know how you say that in Portuguese. After a shocking third goal by Alex Ligalchuk in the opening match week of this year's Champions League. All the way back September 16, 2025. They were down 2-0 in the first half. But Carabag went out to score the final three goals. still all the points in what was an opening salvo to a quite remarkable run to the knockout round by the Azerbaijanis. Since that night in Lisbon, Carabag have gone on to beat the likes of Eintracht Frankfurt.

15:17Copenhagen grabbed the point from Chelsea at the bridge, something, by the way, Everton haven't done in nearly three years, but you're all more for a Carabag-style point, securing themselves as really the tournament Cinderella darlings along the way. Don't know how you say UMBC and Azerbaijani, but Ro, I'll be the first to admit, But back in September, I did not have Carabag beating out Marseille, PSV, Ajax, Napoli and that Royal Rumble cage match of a group stage. It's a bit like the Eurasian footballing version of a Spud Web winning the dunk contest. So tell us, who are they? What is a Carabag?

15:51What type of football do they play? And how did a club from Azerbaijan just bulldoze their way into the knocker rounds of the most prestigious club tournament in the world? Well, obviously, you're not that familiar with Karabag, because you're a Necce Baku man, aren't you, Rog? You've always said that. It's always been obvious. I've seen you my tattoos. You can see it on your face. You're Necce till you die. Yeah, Karabag, for a long time, were not a particularly significant force, even in Azerbaijani football, certainly not in Soviet football before that. They are from the disputed territory between Azerbaijan and Armenia, and Adorno-Karabag, hence the name.

16:24But they haven't played there for more than 30 years because of the war. They play in Baku. But they have been able, in the last decade or so, not only to really establish themselves as the dominant force in Azerbaijani football, but to begin to make inroads in Europe. And I think what's really interesting about that is the way they've done it. Because obviously Azerbaijan is not a major league. It's not a place where players would dream of going to play, unless they are from Azerbaijan, to be honest. Karabakh have kind of mastered the art, and we've seen other teams do this, of dominating a minor league and using that as a passport into European football, which is what an awful lot of players want.

17:05So obviously, they've had their fair share of Brazilians. They've had their fair share of imports from across South America, from across Africa and Eastern Europe in particular. They've been able to attract players to a league that offers a reasonable standard of football to a city that I think feels increasingly modern and cutting edge in Baku. but crucially they can say to them if you come and play for us you will be in the Conference League the Europa League and now the Champions League and that means you get Champions League quality footballers. Yeah, you can come and play in our stadium in Baku named after one of the greatest Azerbaijani football legends of all time Tofiq Baramov the linesman who awarded Jeff Hurst infamous goal non-goal depending if you're English or German and in England's 1966 World Cup final victory, the ball bounced on the line.

17:59He was the linesman who gave it and was, I think this is an apocryphal story, was asked on his deathbed how he knew Germany had conceded the goal and he was alleged to have just said, the siege of Stalingrad. And if that doesn't make you love Karabag, I don't know what will. I'll say success did not come in earnest until 2008 when they hired current head coach Gerben Gerbanov. The manager so nice, they named him twice, known as the Azerbaijani Alex Ferguson Gerbanov, now in his 18th season at the helm. I think Nottingham Forest have had about 5 ,483 managers at that time. He completely transformed the club, securing 11 out of the 12 last Azeri titles, 190 European appearances since his hiring, including Carabag's coming-out party to the world stage two years ago when they so nearly took down Xabi Alonso's end, undefeated by Aleva Kuzin, the Europa League round of 16, losing 5-4 in aggregate after conceding twice in stoppage time in the second leg.

18:59That was an agony, Carabag heartbreak, but also a warning shot across the bow that they could compete with the best in Europe. Also the point where the world started to wonder if it was time to call Alex Ferguson the Scottish Gerben Gerben of. Carabag, pretty unique from other small country domestic giants they are. Should be mentioned, the richest Azari team owned by a state-backed agricultural conglomerate, Azazoun Holdings, presumably flush with free popcorn for life. They sound like something that a company you'd hear about in industry, but they don't bring in the end-of-career cash grab star signings like your Saudi or Turkish or Greek leagues, nor do they sell off their best talent like the Dutch or the Belgians.

19:41Their all-time record spend was all the way back in 2012, 1.5 million. Their record sale, just over 5 million. And Karabag legend Maxim Medvedev has said, quote, we never sign top stars for Gerbanov. All the players are equal. That's a line even Ted Lasso writers couldn't make up. So, Roar, how does a Karabag team on this budget remain successful? And do they offer insight into the kind of teams that can now thrive in this modern incarnation of the Champions League? I think you have to give credit to the scouting for a start. They have an ability to get players in for not huge sums of money in terms of fees, although I would just say that their salaries, I think, are quite generous to that there is a cost to getting players to Azerbaijan, who have proved to be more than good enough to compete in first Europa League and now the Champions League.

20:27And I think that can be testament to casting a wide net. If you look at where they recruit players from, it's not kind of obvious places. They're not trying to kind of compete with Portuguese teams or Italian teams or German teams for players. They're looking elsewhere. Their relationship with agents, I think, will be very strong. But also their pitch. Their pitch is a really convincing one. it is you can come and win a league with us which we will do almost certainly every single year and we can guarantee you European football and for particularly South American players that's a huge attraction I think in a lot of ways Karabag are a slightly further away Shakhtar Donetsk that's exactly what Shakhtar did for a long long time and it's what gave European football Willian and Elano and Fernandinho and all those players who came went Brazil Ukraine Europe I I think Carabao are trying to do something similar, maybe at a slightly lower level, maybe without that level of investment in the initial kind of purchase.

21:21But you're right, Rog. It shows how European football has changed because it's probably better now to be Carabao, a large team in a small league, with all due respect to Azerbaijan, who can dominate it, who can turn that league into a procession so they can then attract players because they want to play in Europe and you can guarantee them that you'll be in Europe. It's probably easier to be them than it is to be an upper-mid-table team in France or Spain. It's probably easier to be Carabag than Valencia, for a start. It might even be better to be Carabag than Ajax or Feyenoord or possibly PSV Eindhoven, because they have to compete with each other in those leagues, so you can't ever guarantee Champions League football, whereas Carabag can.

22:08God, as an Everton fan, but you're on off to be carabin. Quickly, taking a step back for one moment, we are 23 years removed from that Porto-Monaco final that gave us the origin story of Jose Mourinho. Also the last time that we saw two smallish clubs with an asterisk on small there or compete for a final. In this modern age, with a first round knockout by effectively awarded to all the superpower and the leftovers filtered to the playoff phase, those smaller clubs now got to go through an extra round of football just to make it even to the round of 16. It's never before seemed so out of bloody reach for a mid-tier club to compete deep into the tournament, let alone a Carabag, not no further than the 6-0 drubbing that Carabag took to Liverpool and Anfield in the last match week.

22:57This year though, we start to see these teams from the corners of Europe pile into the knockout rounds. Your Carabags, your Bodo Glimps, your Olympiacos, Club Bruges, travelling to back over the Arctic Circle on your Tuesday afternoon could spell real trouble for a team that just played a league game three days prior. Roar, not to get too all-exessential on s***, but also maybe too romantic. What is the hope for small clubs in this tournament? Is there any, will the geography of these teams actually give them any kind of meagre advantage over the smaller-sized clubs that play in France or smaller Portugal?

23:30Is there a world where we see a Carabao sneak their way into a quarterfinal? Yeah, I mean, it has happened before. It is getting harder and harder. Apuel Nicosia, I think, made a quarterfinal about 10, 15 years ago. It is possible that an absolute outsider can do it, but they need, number one, quite a kind draw, and I'm not sure Carabao have got that, because I think for Newcastle, they're not one of the favourites, but they will see, you know, get into the last 16 is a massive achievement for Newcastle in itself. I do think there's a bit of hope, though, mainly in the form of our beloved Bodo Glimt, Rog.

24:03Because if you look at the teams that Bodo have beaten in Norway recently. I think there's no reason to believe that Inter will go there and kind of sail through. It's difficult that, you know, the second leg will obviously be in Italy. But I think there's potential for a shock there. Ultimately, for those sides from the corners of Europe, like you say, who want to kind of make an impact on the Champions League, the deck is stacked against them and is getting more and more stacked against them every year. What you need, I suppose, is regular Champions League football. that's a huge advantage because it means you have access to a better standard of player you need to have to perform as well as possible to get as high up that mega table as you can to try and get a home leg second and you need a bit of luck you need to hope that the team that comes out from the bottom half of the draw is is the slightly easier one of the two and at that point you might be able to make the last 16 and then you'd need to kind of roll the dice a little bit on getting through.

25:01It's a shame, not maybe for Carabao and Bodo, who I think are from countries that would always have been outsiders and would probably always be outsiders in European football. I think for teams like Olympiacos or for the Dutch teams or for the Portuguese teams, it is a shame that everything has been weighted against them so much. And I actually think that the bigger teams from the bigger countries suffer as well because it removes just a little bit of the magic from the competition and that makes it slightly, just a tiny little bit less attractive. Karabag will host Newcastle at the aforementioned Tophik Barama of Republican Stadium long live Tophik this Wednesday February 18th 12.45pm Eastern Time it's a 9.45pm kick-off local time Rory so bring your PJs your hair rollers and several six packs of whatever the two fans will be drinking okay Rory Dahmer prediction time how do you see this one playing out?

25:54Yeah I can't see I can't see Karabag going through over the course of the two legs but I think they'll get a result in Azerbaijan The 6-0 against Liverpool was really weird, because in every single other game, Carabao have been competitive. They haven't always won those games. But even against Chelsea, they ran them really close. They were leading at one point. It wasn't an easy game for Chelsea. So I would think Carabao will draw the first leg, maybe 2-1, but ultimately Newcastle will go through. I believe Carabao will play valiant, prideful football and lose 2-1. I think Tonali will score and that ginger Benedict Arnold, Anthony Gordon will net the winner.