Jermain Defoe: boobsmacked

9 Sep 2025 · 53 min · 26 chapters

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In short

A comedic, tabloid-style life recap of footballer Jermaine Defoe, focusing on his career moves and repeated “kiss-and-tell” scandals involving cheating allegations, explicit messages, and pranks, alongside his charity work and notable relationships.

Guests

Jack (host) and Zach (co-host) plus new guest Jack Stewart, the show’s producer (long-time “lurker,” first-time on-air). No other guests are interviewed.

Guest backgrounds

Jack Stewart is an Upshot producer; he’s described as doing charity work and generally well-liked.

Key claims

Defoe was “boob smacked” in a 2007 News of the World story (Rachel, “30D” claims). He allegedly used Viagra to prank Carlton Cole (via Wayne Rooney). Multiple cheating allegations follow: Alexandra Burke (dumped; song lyrics), nurse Kirsty Crummy (explicit-photo/threesome claims), and later Donna Tierney (fake wedding for OK! Magazine; Range Rover propositioning). Post-retirement, he forms a thruple with Alicia and Paige, later photographed in a car park.

Notable examples

East London youth at Senrab FC; West Ham/Spurs/Portsmouth transfers; 5 goals vs Wigan; Toronto FC signing via Drake; OBE for charity; Rangers league win; vegan stint; candle “marry me” proposal.

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

Chapters

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Jermaine Defoe's Reputation

0:36 to 1:04

Discussing Jermaine Defoe's controversial antics and public persona.

“You sent a message, and it turned out the seller was super chatty, kind of funny, and an avid cyclist.”

Jermaine Defoe's Reputation

2:04 to 3:10

Discussing Jermaine Defoe's controversial antics and public persona.

“It's been a long awaited debut, actually.”

Defoe's Early Years and Career

3:10 to 5:30

Exploring Jermaine Defoe's childhood and rise in football.

“So Jermaine Defoe was born in East London in 1982.”

Transfer to Spurs and Early Success

5:30 to 6:28

Covering Defoe's transfer to Spurs and his early successes.

“Which, you've got to say, is a bit soon.”

Controversial Moments and Scandals

6:28 to 8:18

Retelling Defoe's infamous biting incident and personal scandals.

“Jermaine loses his head and sinks his teeth into Javi Mascherano.”

A Look at Defoe's Relationships

8:18 to 9:40

Discussion about Defoe's relationships and media portrayals.

“all the time he kept comment complimenting me about my boobs he said they must be fake because they are so huge.”

Defoe's Legacy and Future

9:40 to 14:00

Speculation about Defoe's future in football and his legacy.

“You don't see the ice cream that often anymore.”

Jermaine Defoe's Move to Portsmouth

14:00 to 15:25

Learn about Jermaine Defoe's transition to Portsmouth and the controversy over his contract negotiations.

“She's very involved, which is quite common.”

The FA Cup Experience

15:25 to 16:44

Explore Defoe's experience during Portsmouth's FA Cup win and his career challenges.

“This is the season that Portsmouth win the FA Cup.”

Return to Tottenham Hotspur

16:44 to 17:45

Discover how Defoe returned to Tottenham Hotspur and performed in his second spell.

“so only a year after he joined Portsmouth Harry swoops for him and for the third time signs him Harry loves a yeah just re-signing a player who are the others?”
Show all 26 chapters

The Carlton Cole Prank

17:45 to 19:37

Hear the humorous story of a prank involving Jermaine Defoe and Carlton Cole with unexpected consequences.

“And then later, Berbatov and someone else.”

Relationship with Alexandra Burke

19:37 to 21:41

Learn about Defoe's brief relationship with singer Alexandra Burke and the ensuing scandal.

“And then he said, I was the quickest person around that pitch.”

The Move to MLS and Drake's Influence

21:41 to 24:24

Understand Defoe's move to Major League Soccer and the role of rapper Drake in the recruitment.

“But I do think it's quite a clever defense if you are shagging her because surely no one would be that rude.”

Life at Sunderland and Unique Job Listing

24:24 to 28:00

Explore Defoe's time at Sunderland and the intriguing ad he posted for a personal assistant.

“Yes, it is Canadian rap sensation, Drake.”

The Demands of Jermaine Defoe's Job

28:00 to 29:40

Explore the extensive requirements for managing Jermaine Defoe's brand.

“It says, here's what the 60k job will involve.”

Funny App Ideas and Personal Branding

29:40 to 30:40

Discuss the humorous potential of Defoe's personal app and branding ideas.

Defoe's Romantic Misadventures

30:40 to 31:31

Delve into Jermaine Defoe's romantic life, including awkward encounters.

Defoe's Romantic Misadventures

31:37 to 32:00

Delve into Jermaine Defoe's romantic life, including awkward encounters.

“web like restoring a vintage motorcycle from a 50 page restoration block or finally break down that long article you've had open for weeks gemini and chrome is here for it ready to make anything online makes sense?”

Jermaine Defoe's Charitable Impact

32:45 to 35:30

Highlight Jermaine Defoe's charitable efforts and genuine friendships.

“and everything you need to stay ahead of your mini-league rivals.”

Scandals and Marital Issues

35:30 to 37:55

Unpack the controversies surrounding Defoe's personal life and relationships.

Defoe's Career and Retirement

37:55 to 41:40

Review Jermaine Defoe's football career and achievements post-retirement.

“from Sunderland who I think they need to offload expensive players he has a stint at Bournemouth and then of course Rangers he goes to Rangers where he wins the league I mean Stephen Gerrard is his manager right?”

The Marriage and Quick Downfall

41:40 to 42:00

Detail the rapid rise and fall of Defoe's recent marriage.

“So I think it's not the first nurse we've had in this story.”

Jermaine Defoe's Sham Wedding

42:00 to 44:35

Explore the bizarre circumstances surrounding Jermaine Defoe's wedding and its implications.

“I mean, Range Rover, if you've got to do it, then Range Rover's probably more spacious.”

The Throuple Revelation

44:35 to 47:20

Delve into Jermaine Defoe's unconventional relationships and his foray into a throuple.

“Can't wait to spend the rest of our lives together.”

Tabloid Scrutiny and Scandals

47:20 to 49:32

Discuss the intense media scrutiny Jermaine Defoe faces post-retirement and the impact of his relationships.

“Jermaine Defoe is papped in a car park I quote from the tabloids enjoying a 20 minute rendezvous with a mystery woman in the back seat of his motor so good that he's finally got it back at her Same car, Range Rover.”

Is Jermaine Defoe a Romantic or a Cheater?

49:32 to 52:08

Analyze whether Jermaine Defoe's actions reflect a hopeless romantic or a cheater.

“Which I guess brings us nicely to the sort of verdict.”
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Transcript

Automatic transcript. May contain errors.

0:00Tee off on the Turkish Riviera, Europe's premier golf destination. with championship courses in Bilek and Antalya, luxury all-inclusive resorts and year-round sunshine. It is the perfect getaway under the Mediterranean sun. Play immaculate fairways designed by golf legends, then unwind beside stunning beaches and five-star hospitality. Search Turkey on TripAdvisor now to book your ultimate golf holiday in the Turkish Riviera. This episode is brought to you by Facebook. So you were scrolling on Marketplace, and there it was, the bike you'd been searching for. You sent a message, and it turned out the seller was super chatty, kind of funny, and an avid cyclist.

0:47The next thing you know, you're in a cycling crew. Well, a community cycling group. The thing about Facebook, you might find more than what you're looking for. From a browse to a bike ride, this summer, find more on Facebook. Hey Chicago, class it up with Crocs. You know back to school is coming in fast. So why wait to find your new Fave footwear? Step into a local Crocs store and step into your new look. Try it, style it, make it yours. Because the right pair doesn't just show up, it shows off. First day fits, handled. Walk out ready for whatever's next. Visit your nearest Croc store today. He's the pint-sized poacher with a naughty streak.

1:35Jermaine Defoe bonked lap dancers, bit opponents, and spiked his teammates with Viagra. From bogus weddings to backseat rendezvous, meet England's friskiest forward. Welcome back to The Upshot. My name is Jack. Zach is here as ever. Hi, Jack. Hello. And we are welcoming a brand new guest. although not so new because he's been lurking behind the cameras for some time, coming out of the shadows, is Upshot producer Jack Stewart. Thanks for having me. Welcome aboard. Yeah, long time lurker, first time? Big time lurker. First time talker? Yeah, I made one quip once. How'd it go? It made the edit, so yeah, pretty good.

2:17I mean, you did do the edit. It's been a long awaited debut, actually. Yeah, we've been pushing it for a while. finally here finally here on the sofa the big debut yeah it should be excellent I will promise no less than excellence that's all we ask for I would say Zach having done the research for this that I agree that he's a nice guy unless you're going out with him yeah I think generally people have good things to say about him he's done he does a lot of charity work Jermaine Defoe OBE we should say yeah he was OBE'd what do you call it gonged gonged gonged for his charity work so yeah I think he's he comes across as a nice guy.

2:58But yeah, there is, unless you're going out with him. There is a naughty streak, as discussed, and there are some hilarious capers that come off it. I'm sure it's all just a misunderstanding. Yeah, yeah. They're just a boob smacking, as we'll see. Yeah, should we get into it? Yeah. Take us back. So Jermaine Defoe was born in East London in 1982. He started out playing football for Senrab FC, this pretty famous Sunday League team in East London. It's where John Terry, Ashley Cole, Ledley King, a few others came through. And he ends up joining West Ham's Academy when he's 16. So Harry Redknapp is manager at this point.

3:33And Jermaine's living in digs there alongside Joe Cole, among others. They get up to a bit of mischief together. So Joe Cole tells this story of having his girlfriend over one night. They're about 16 at this point and they're watching a film in bed. But Joe says, in his words, they're doing things 16-year-olds do. which you can probably fill in the gaps yourself. Anyway, this girl's dad arrives at some point to collect her and Jermaine meets him outside. He's like, yeah, yeah, just come straight up, straight up, leads him up the stairs, bust straight into Joe Cole's bedroom. And he's just like fumbling around under the covers, like trying to compose himself.

4:16And Jermaine's just there giggling behind the dad, apparently. So just a straight up, stitch up. Yeah, yeah, I think he knew what he was doing. Because that's the sort of thing where the dad might properly lose it. Fuck it, door! Dragging Joe Cole out by the hair. Yeah. I don't know if there's much of the problem. It was always quite short, though, wasn't it? By the buzz. Yeah, yeah. So, yeah, he had Jermaine in 2000 that season. He ends up going on loan to Bournemouth, who are in League One. And he absolutely smashes it there. Scores in 10 consecutive games. and the following season he gets parachuted straight into West Ham's first team squad.

4:55Jermaine has a great first proper season in the West Ham first team. He's their top goal scorer, despite the fact he's mostly playing as a sub. What year is that, sorry? That would be 2001-2002 that year. Still Harry, just the end of Harry. No, it's Glenn Roder. Oh, it's about to go to shit, isn't it? Yeah, so the following year, Jermaine plays really well again, scores a lot of goals. But despite his best efforts, West Ham are relegated. It's 2003 now. And less than 24 hours after their relegation is confirmed, Defoe hands in a transfer request. Which, you've got to say, is a bit soon. And he does stay, but they end up selling him the following January to Spurs.

5:40Because this is when West Ham get pillaged for their star players. Yeah, there's like... It's when Joe Cole goes to Chelsea. Joe Cole goes to Chelsea. Michael Carrick leaves for Spurs as well. Anyway, there's a lot of hype around Defoe when Spurs sign him. He's this young, exciting, quick English striker who scored a lot of goals for West Ham. And instantly, he begins to deliver. So he scores on his debut. He's voted Spurs Player of the Year for 2004. and this mid-2000s era is a bit of a golden age for Spurs strikers really. They had Defoe, Robbie Keane, Berbatov, Mido as well, who was briefly really good.

6:24And maybe all that competition raises the stress levels for Defoe because in a fiery fixture against his old employers West Ham in 2006, Jermaine loses his head and sinks his teeth into Javi Mascherano. What a clip. Watch this.

6:44Just a nibble on the shoulder. I had no idea that happened.

6:53I think he's just trying to whisper something in his ear. That could have happened to anyone, frankly. Yeah. But there is an even bigger scandal coming for Defoe because in 2007, the News of the World revealed that he's been cheating on his fiancée with a girl called Rachel that he'd met at nightclub in London. So the News of the World article was headlined, Defoe does the double. And it uses a word that I've not heard before or since to describe him. It says Defoe is boob smacked because he likes big boobs. Oh, like gobsmacked? Yeah, it was a terrible pun. They're saying what, he saw her boobs and he was boob smacked.

7:33He was boob smacked. Can you use it in a sentence, please? Jermaine after seeing Rachel in the nightclub and admiring her 30D boobs he was boob smacked boob smacked now I understand when you first said it I thought maybe he was going to be smacked in the face with a boob and it was like a thing that could also be he was injured sort of like motorboating but it's being it's a more passive experience do you know what I mean similar sorry mind's up to you racing the receiving end of a motorboat I was falling down a rabbit hole yeah the receiving end of motorboat yeah a passive motorboat yeah yeah boob smack this was just a line from the article but the whole thing is basically a kiss and tell with her um so she says he was mesmerized by my 30d boobs in fact he talks about my breast a lot all the time he kept comment complimenting me about my boobs he said they must be fake because they are so huge.

8:31But they're not, is her point, I guess. I mean, let's not dwell on the boobs too much, but she's saying they're not fake. They're not fake. Oh, no, they're not. That is boob smacking. Can it be boob smacking? Yeah, I guess. I'm boob smacked at that. Oh, yeah, yeah, yeah. Rachel also goes on to give quite a graphic description of Defoe's manhood. She said, he used to have a nickname for his thing. He wasn't very modest and he always called it the Hulk. It was quite distinctive because he has a strange skin pigmentation down there, which means it's the colours of Neapolitan ice cream. Oh my God.

9:07This is a chocolate vanilla and chocolate vanilla strawberry. Yeah. Does she mean in the vertical stripes? I presume so. That's fascinating. I've never seen a knob like it. I'm just trying to... I reckon it's more likely to be horizontal stripes and there's three sections. Sorry to do this. Like a tricolour. Yeah. Yeah, it's sort of flying the flag. I'm thinking maybe the head is like the, I don't know, is pink? I don't know. Yeah. Which else would be, you know, so. Yeah. It's going to be the head, right? Yeah. I mean, I've never seen a Neapolitan knob before. Don't even really. You don't see the ice cream that often anymore.

9:45No, yeah. Do you think that's off play? Middle aisle of Lidl probably. Yeah, you'd probably get it. Yeah. It's probably referred to as like a different region of Italy. I don't think I'm ever going to look at Neapolitan ice cream in the same way. Has that ever been mentioned before or since About Jermaine Defoe Or indeed anyone I've never heard it before Neapolitan Nobs That's two things I've never heard before Both in this article It's a good album name Yeah Neapolitan Nobs Or Boobsmacked That's the debut That's the first track on the album It's very thin but it's got a big thick crust Oh god The other thing is I feel like this era So we're in the noughties we've obviously read a lot of these kiss and tells it's quite common that footballers have a nickname for their dick and I don't think you hear about that anymore but rightly so because it's fucking childish yeah but do you know what I mean?

10:38that's the Hulk how far are you taking that nickname? is it like while you're shagging you're being like do you like the Hulk? do you like the Hulk? yeah the Hulk is angry and you won't like him when he's angry Hulk smacks I wonder if give them like human names yeah those are always my favourite like pet names is when people give them unusual human names like Bruce, Steve my cat RIP was called Maurice Maurice which was good, quite nice that sort of makes me picture a man in like a roll neck jumper Maurice sort of like East End kind of camp inexplicably got a picture of it Maurice is Roy Keane's middle name as well, isn't it?

11:27Yeah, but I think he would say Morris. We've discussed this. Yeah, we've discussed this. Roy Keane is Morris. And Roy Keane would not have a nickname for his cock. Do you agree? Having a nickname for your cock is a bit like, I think it's, I don't know why, but I think it's like someone who's been a bit babied by their mother, and now they need like these sort of just like... Yeah, it's quite infantilising. Yeah, I don't know why I'm getting Freud about this, but something about that to me screams like, grow up. Yeah, yeah, yeah. What, like if your mum calls it your winky or something? Yeah, maybe it's that.

11:58I don't know. It's just like the need for a pet name for your dick. It's like, stop humanizing it. Yeah. It's a Neapolitan knob and you are boobs smacked. If you had a hulk of a penis, you'd have a nickname. I don't think you need one. If you've got a big cock, why do you need a nickname that means it's big? It's not a fucking 1910s shipping vessel. I don't know. I'm trying to think of the other names. You do hear quite often the same sort of names around. Yeah, they're never that imaginative. If you'd come up with a Neapolitan character, Marigama, say. or I don't know someone from Talented Mr.

12:27Ripley that would have been good or an ice cream salad if it was called like Minghella anyway mine's the pecan yeah did you imagine the pecan yeah what flavour is he got probably vanilla if I'm honest mine's a mini milk a vanilla mini milk fish food onwards and upwards though and it's now the summer of 2007 when Spurs make the quite surprising signing of Darren Bent for 16 million quid, which is quite a lot of the time. I mean, he was good for Charlton. A bit of a like for like fast. Yeah. It's just odd because I think Defoe was, was Defoe a bit injury prone at this point? He has had quite a lot of injuries.

13:10Yeah, he'd been in and out of the team for Spurs as well because they had these other good strikers I was mentioning before. Yeah, maybe they're just going for a depth thing. But anyway, Jermaine's suddenly in competition for his place and he publicly says, I'm going to stay and fight for my place. but by the end of 2007 he's getting a bit sick of basically being rotated around with the other strikers and then a call comes from an old friend Jermaine, it's Harry come and join me at Portsmouth and it's Harry Redknapp yeah so he's his Pompey manager and this is quite a different Portsmouth certainly than the one we know today so they're kind of like reliably mid-table Harry Redknapp's at the helm they've got quite a good squad you know they've been spending a lot of money which will ultimately be that downfall and Jermaine you know he's already worked with Harry at West Ham where he thoroughly enjoyed himself and so he thinks do you know what I'm gonna head off I'm sick of playing second fiddle to Darren Bent so he goes goes and has talks with Portsmouth and it's all looking good until this cozy reunion between him and Harry is disrupted when contract talks get serious and Jermaine's mum Sandra is she's in there with his agent.

14:18She's very involved, which is quite common. Is this again, going back to his, why is this where you got your theory? You researched this part. Totally concocted. He's got a nickname for his Willie and his mom does his contract. Anyway, so Sandra, she apparently is insistent that Jermaine should get a goal bonus on top of his salary, which at the time is, you know, now it's standard, but at the time it's like a relatively new thing. And Harry Redknapp isn't impressed. His reaction, as he recalls later was a goal bonus? He's a striker. What do you think we'll be paying him 50 grand a week for to fucking miss him?

14:54I think that's a fair point. You can't be demanding a goal bonus. I don't get a bonus every time I put up an Instagram reel, you know? Yeah. Well, I should have my mum in my negotiation. if your mum had only come to the contract talks. Yeah, but they are standard now, aren't they? It's weird. Yeah. It is your job. That is literally, that is literally what you've done. Anyway, this is free spending Portsmouth, so I think they just agree. The deal gets done and Jermaine Defoe heads to the south coast. And they have a huge season. This is the season that Portsmouth win the FA Cup. So they get to the final and then it's Cardiff, which is a decent draw.

15:32And they win 1-0. Unfortunately, Jermaine plays no part because he's cup tied. So he does not play in the FA Cup for Portsmouth. But he was there. He's around there. He's near the FA Cup. He actually doesn't win a lot of trophies throughout his whole career, does he? He wins the League Cup with Spurs later. Yeah, but again, he's injured for the final. I really, I get it. He has an unfortunate thing of being ruled out for big games. He wins the title of Rangers, as we'll come on to. But yeah, he's no part of a Pompey FA Cup winning team, but it's nice to be around it. And he's still the following season banging them in for Portsmouth.

16:06He's a really good, reliable striker. As for Harry Redknapp, he is the first to realise that Portsmouth's castle is built on sand and they are spending way beyond their means and are about to have to start flogging all their players. So Harry's, you know, starting to think about jumping ship when a call comes in from Tottenham Hotspur who snap him up as manager. So he hotfoots it over there. And for Defoe, you know, things are starting to look a bit wrong. There's talk that the club maybe can't afford all these players. His mentors left. And pretty soon he's agitating for a move as well. and in the January transfer window that year so only a year after he joined Portsmouth Harry swoops for him and for the third time signs him Harry loves a yeah just re-signing a player who are the others?

16:53Krenkjahr Nico Crenshaw yeah Ben Watasio Okoto as well he had in two clubs didn't he? did he? he had him at QPR as well Peter Crouch as well Peter Crouch I actually get it Eddie Howe's a bit like that if you've worked with him before you know you can trust him if you're that sort of manager who's like really involved 10-Hag yeah 10-Hag less exactly 10-Hag so back to Tottenham he goes you notice Jermaine Defoe usually moves in the January transfer window which is quite rare I think but he's the sort of player you would buy in January I think because he's just going to come and give you some goals immediately anyway he does very well at Spurs in his second spell the 0-9-10 season is probably his best scores 24 goals including three hat-tricks one of which is five goals against Wigan five in one game Yeah, one game.

17:40It's the, I think at the time, he's only the third player to do it. Shearer and Andy Cole. And then later, Berbatov and someone else. He's playing regularly for England at this point, which of course you wouldn't have missed a game. I am a big fan of England, of course. The three lines. It's three, isn't it?

17:59Those lions. That was our lions. Yeah, Jermaine. So he's like, I don't know if you'd say he's like first choice striker, because obviously you've got Rooney. but he's sometimes paired with him off and off the bench. He's very much like a key part of every squad and very much one of the lads as well. Him and Rooney and the other senior players, they're all really matey. And when fellow striker Carlton Cole is called up for a friendly in 2009 against Spain, Jermaine and Wayne Rooney decide that he is the perfect character to play a little prank on because Carlton's quite bright-eyed and bushy-tailed, enthusiastic.

18:36He's up for anything. and so in the dressing room before they run out for training Jermaine and Wayne take him aside and are like, Carlton do you want some vitamins that'll really help and Carlton's like oh yeah I'm big on vitamins, yeah yeah so they hand him a little blue pill which of course was Viagra and poor old Carlton swallows it and within about 30 to 45 minutes he is left with a big old boner he has to stagger through training with an erection that lasts three hours he says wow so that can't be very helpful when you're trying to run around I imagine no mark someone at a corner yeah well it's quite good for putting them off isn't it poking them in the back it's probably a crime but is it Erling Haaland who farts at corners yeah I think having a boner pressed into you would be more that would be yeah you'd give the defenders some space or the attacker actually I should say it's perfect for a striker Carlton said later about it he said the stonker was there I wasn't sexually aroused but it was just there.

19:38And then he said, I was the quickest person around that pitch. I had three legs. Makes me think he's told that story before. The Hulk and the Stonker. Yeah, the Hulk and... The Stonker's a good name for a bone, for a cog. Yeah, so quite a good nature prank, I guess. Quite a weird one, I suppose. Probably a crime. Yeah. Almost definitely. Again, just, you know, misunderstanding. You probably shouldn't be, especially as a professional sportsman, just taking random pills from people who don't... Yeah, what if it had been like an ecstasy tablet? or steroids got banned yeah I think Viagra's it's quite funny that's just knocking around as well I do remember a phase of like people having it on nights out as a joke Viagra yeah spiking people with it not spiking but just like lines of it taking it and finding it funny I won't go into details we've said 30-45 minutes that was a research or did you happen to roughly my experience anyway Carlton's not the only one swinging his horrible bone around where it's not wanted because Jermaine is at it too.

20:40In 2012, he begins probably his only sort of like celeb relationship. He goes out with Alexandra Burke, who is the X Factor winner. God, there's a blast from the past. Yeah, I actually rewatched one of her songs just now. And he goes, yeah, it's quite like of its time sort of R &B pop. You know, she's got one with Flo Rida, one with Neo. Okay. All the comments are like, how did she not get bigger? But it's like, it's quite like a dated genre now i think yeah yeah yeah that's good quite talented emotional um sort of talent show yeah yeah so she's definitely not bad i don't know what she's up to now but anyway they're having like quite a it's a relatively brief relationship but it's it's she describes him as my best friend you know that sort of thing right she's she's head over heels until germaine is accused once again of doing the dirty so the tabloids published an interview with a nurse called kirsty crummy um who says that they've been shagging um she she says that they met on facebook which is kind of sweet now actually isn't it how do you meet on facebook you just see them in a group or something yeah i guess it's like mutual friends got poked yeah yeah poked by the hulk yeah with carlton's corner

22:01I forgot my Carlton stunk but like how do you even come across random people on Facebook do they just DM you maybe I don't know who knows but what happens next according to Kirstie is that Jermaine begged and pestered her for explicit photos and asked her for a threesome I've noticed a standard tabloid devices if someone asks for something they begged so take it with a grain of salt but yeah she says they had an affair Jermaine's actually quite unkind in his response because he tweets and basically says, he points out that Kirstie bears a slight resemblance to the comedian Peter Kay and just says, apparently I'm shagging Peter Kay, which is mean and wrong.

22:40But I do think it's quite a clever defense if you are shagging her because surely no one would be that rude. And I think it probably buys him some time with Alexandra Burke. Unfortunately, there are then more cheating allegations and eventually Alexandra's had enough and she dumps him. And she then writes a song slagging him off Which includes a lyric You're used to fucking substitutes Which is sort of wordplay on cheating But also warming the bench It kind of works Yeah, yeah, it's also Dig at him, isn't it, really? Well, yeah The other lyrics were a bit more just like I thought you were my friend It was a bit sad But I enjoyed that little dick Not sure Jermaine did Anyway, he's onwards and upwards He has a great Tottenham career.

23:27There's regular sort of top six finishes. There are Champions League games. Again, this thing of like, when you look at a big game, he's weirdly absent. So like, I don't think he was in that famous Inter Milan two-legger. Where, you know, when you came back from like 4-1 to 4-3 and it was in a way felt like a win. Do you remember that? Bale just shredded Mike on. And then the home leg Tottenham won 3-1. That was like Bale becoming a megastar. Anyway, as for Jermaine, by 2014, it's time to move on. He's had two great stints at Tottenham by this point. Both of them, like, you know, sort of 150 games each.

24:00He scored more than 100 goals for the club. But, you know, there's a bit of a sense he's probably lost his pace by this point. He isn't quite, you know, the player that they want going into big Champions League challenges. You've probably got the likes of Harry Kane starting to come through. He's told him everything he knows, yeah. Yeah. So, you know, for Jermaine, though, it's not like he's in a bad place. There's plenty of clubs in the Premier League who will have him and, you know, might be a great move. You know, maybe he'll go back to West Ham. Michael Landrop's doing some quite exciting things at Swansea.

24:26But then Jermaine gets a phone call. Hello, is this Jermaine Defoe? Yeah, who's this? This is Drake. Yes, it is Canadian rap sensation, Drake. Hotline bling star. What do you want? You used to call me on your cell phone. Oh. Drake, it turns out, when he's not recording, he's already getting quite big at this point. Yeah, he's quite... I don't know if he was a big Defoe head before, because he's very into British culture, isn't he? He loves his grime. And he funded Top Boy, you know, the series. He saw the first two series and then approached them. It was 10 years later and basically was like, I'll pay for you to make more.

25:13Yeah, he likes English culture, I guess I'd call it. I don't really know. Yeah, he's a negative fire. and you know if you are an Anglophile living in Toronto he named himself after Sir Francis Drake I think that much that much he lionises English culture much like you Jack oh yeah just the same what's the curry favor with Elizabeth I which one is Sir Francis Drake he's not the potato guy is he no Francis Drake he was is he an explorer is Walter Raleigh the one who brought the potato back I don't know that era though yeah one of them yeah you know one of your heroes oh yeah yeah and one of Drake's I thought Walter Raleigh made bikes or something yeah probably said family no idea Drake you know obviously besides Sir Francis and you know Richard Attenborough and Elizabeth II his other grey hero is a little known English striker by the name of Jermaine Defoe who he's always always loved and Drake is working as an ambassador for Major League Soccer side Toronto FC who are on the hunt for a new striker.

26:19So when they hear that Defoe's moving on from Tottenham, they swoop and, you know, sending in Drake is a masterstroke. What is it about Defoe that's just irresistible? He's pretty fucking handy, no? Yeah, I mean, I think probably in the MLS. He was still relatively young. How old was he at by that point? He was probably 32, 33 or something. Yeah, he's only 42 now. So yeah, about that. Early 30s. Early 30s. So he'd do a job in the MLS. Well, he does. So when Drake calls, you come. So he heads straight over to Canada. And he bangs in. I think it's 11 goals in 14 games. So got their money's worth.

27:01But despite being prolific on the pitch, he does struggle to settle into a life of maple syrup, dogshit teammates, and unnervingly pleasant locals. Anyway, so after a year there, he is soon agitating for a move back to Britain. And so, you know, Toronto, it's a cosmopolitan city for all its faults. It's, you know, it's a very pleasant place. There's only one place you can head after that, Wearside, because Dick Advocats Sunderland have come calling. And clearly the hectic pace of life on Wearside is a bit much for Jermaine because shortly after joining, he puts up an ad for a personal assistant.

27:41So you might be wondering what a personal assistant to a Premier League footballer, what that job might entail, maybe sorting out his calendar, replying to some emails, booking hotels. But it turns out Defoe is a slightly more demanding boss. So this is the advert he posted. It says, here's what the 60k job will involve. manage and organize calendars for individual family members create an inventory for holiday villas so kind of standard stuff then it gets a little bit more exacting create a global brand for the Jermaine Defoe name book all social events such as theaters, concerts, cinema and musicals create Defoe's own clothing line slash fragrance for sale at his website select and organize his wardrobe produce Defoe's own iPhone apps so you need to be a coder as well as well as sort of a clothing designer brand guru grow his online database and social networking platforms and be flexible to travel abroad and across the country throughout the year at short notice and on call 24-7 that's like four jobs what would the Defoe iPhone app do?

Read the full transcript

29:01ready question yeah you can do you can engage with his global brand you can engage with his global brand it generates penis names yeah yeah I love that it's just like you know once you've once you once you finished off the clothing line this afternoon do you reckon you could just knock up a global brand for us and then code the app yeah code the apps as well obviously and also come up with the app idea yeah I actually have no idea what the app would do highlights Yeah

29:34Also You know when you're talking about the managed calendars For family members which looks like it's like his mum And dad and siblings and it also Says family pets Manage their fucking calendar Where was this ad Place On his app It's a very circular That's what you go there for To get the chance to work with him on his brand I wish he'd done a fragrance I think that would have been fun have any of these things happened I well I think whoever he hired is slacking a bit because I've not I'm yet to see the Defoe clothing range we're not working with the app first and then obviously once that's done then the clothing line, the fragrance and the global brand will follow that dog's calendar is seriously well colour coded

30:24that's literally five jobs as a team 24 hour short notice on call as well like christmas day you get a call you knock up that global run now um to be honest though defoe could probably do with a personal assistant to help with his chat up lines uh because around this time there's a pot bitch story about him meeting this woman at a charity function for sunderland and apparently over the next few weeks he'd text her each friday uh asking if she'd like to come and see him and the two things that he always sent to entice her number one dick pics and number two free tickets to a sundling game which would you rather yeah well this was the season that they got relegated so not entirely sure which one of those prospects was more unappealing is that like a dick pic is sort of a greeting in that context it sounds like it is just like occasionally occasionally you'll get in touch and it's just like dick pic and you're in row row b block seven she just thinks you're getting a picture of somebody this episode is brought to you by google chrome you think you know a browser but gemini and chrome that's new it can help you with practically anything on the web like restoring a vintage motorcycle from a 50 page restoration block or finally break down that long article you've had open for weeks gemini and chrome is here for it ready to make anything online makes sense?

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32:30Find the biggest voices in sports on the Sports Social Podcast Network. Like me, Andy, from Let's Talk FPL, you're home for everything Fantasy Premier League. Whether you're playing for the first time this season or you've spent years picking the wrong captain, I've got you covered with transfers, captaincy, chip strategy and everything you need to stay ahead of your mini-league rivals. With new episodes throughout the week, all season long, search for Let's Talk FPL wherever you get your podcasts and let's get you that mini-league win. Sports Social Podcast Network. I screamed. Sounds like a nice day out.

33:02Cumberland, frankly. I do feel hungry now. I'm not in a hot way. Something sweet. So it's also during this spell that Jermaine befriends Bradley Lowry, the kid who was ill with, he had a rare form of cancer, he was a Sunderland fan. And Jermaine comes out of this really well. He met Bradley when he was a mascot for a Sunderland game and Jermaine was captain. And they strike up this friendship. Defoe visits him a lot, takes him to games and events. It was really lovely and genuine. a six year old boy right six year old boy yeah but DeFoe really goes above and beyond I think for him I think he's still in touch with his family no he is yeah because we should say that like a lot of footballers do like a lot of like actually really impressive charity work with their free time that they don't have to do including like you know like someone like John Terry actually does a lot of like really good stuff I think it's worth mentioning because we always tell the other side of their lives but even by those standards Jermaine Defoe sort of like I don't know it just felt like a genuine friendship with Bradley John Terry stands on the end of the hospital bed and pisses into a glass to entertain the it's what they want to see that'll be my request I think John Terry is actually really good on it but like loads of players are they're pretty amazing but Jermaine Defoe also prior to this had set up like a charitable foundation where he gives a lot of money to kids yeah I don't know what the specific focus is but yeah he does he does a lot of really good work I think he's deep down a really good person.

34:42Yeah. Apart from the shagging. Anyway, apart from the shagging. Verdicts later. Yeah. I get the feeling as well that he's not popular with every local family in Sunderland though because around this time he's accused of breaking up a couple of marriages. Oh, there it is. So first, first the press report that Jermaine has hooked up with this Geordie lap dancer who then ends up dumping her husband in an asda car park and moving in with defoe that's tough yeah i i quite i mean it's tough on the guy it was on valentine's day no is that because he was being romantic and she was like i can't do this anymore or maybe because he brought her to asda for valentine's day

35:32final straw as to got these they go off today at the end of the day the flowers are actually cheaper he did he did have a juice yeah it's like christmas day turkey shopping yeah i think apparently he did um yeah i think they were like on a break and then they'd arranged to meet up on the neutral ground it's nowhere good to get dumped were they married they were married so we're good to dummy a husband but no one has to car park on Valentine's Day also I quite enjoyed the angle that the press had was that he was they'd apparently spoken to to pals of this bloke who said that he was especially pissed off because he was a Newcastle fan which does twist the knife a bit it's like not only has your wife left you but she's left you for the star striker of your hated rivals can you imagine every time Jermaine DeVoe scores you see it like you're just in the pub or whatever match of the day it's like oh for fuck yeah yeah yeah it's not good uh and then a year later the heart fm radio presenter ben weston accuses defoe of having an affair with his wife um so apparently she was a hot tub saleswoman and defoe had come into her showroom to take a look at the tubs and they'd ended up shagging what do you think it was like i mean that sounds like a porn film why don't we try it out yeah get the bubbles going imagine if you walked into a hot tub warehouse whatever they're called shop and Jermaine Defoe was shagging the salesperson in a bubbly bath yeah Neapolitan ice cream knob just poking above the surface of the water yeah PAs in the car knocking up a global brand shit was it did he he Defoe I don't think he denies that they hooked up but he says they had nothing to do with the breakup of their marriage and she actually says that she left Ben Weston for other reasons which we won't get into anyway Sunderland as you say they end up relegated that's the David Moyes season which we've done an episode on Sunderland where we get into all that but while Jermaine is staring down the barrel of a season in the championship there is some good news because this is the year he gets his OBE for his charity work so this is good news and he quickly heads off from Sunderland who I think they need to offload expensive players he has a stint at Bournemouth and then of course Rangers he goes to Rangers where he wins the league I mean Stephen Gerrard is his manager right?

38:05Is he? Yeah Sort of 2020, 21 Yeah that was because it was their first Celtic had won nine in a row was it and then Rangers got the time It's a seriously long career if he was playing at the first time in 2000 Yeah and he only finished playing like a couple of years ago so he does win the league I think he's his appearances are relatively limited. He actually, he went vegan around this time, 2017 to prolong his career. Oh really? Yeah. That worked. He had a long career. But he does hang up his boots, which means at the end of his career, the numbers are pretty good. He scored 163 Premier League goals in just under 500 games, 496.

38:42And he played for England 57 times, scored 20 goals. That's a good, good return. Good career. Especially, I think, you know, he came off the bench a lot, particularly for England, but just in general, he would. So those numbers are almost better than they look. But retirement is where the scandals really start to kick off. So in 2021, while he's still finishing up with Rangers, Jermaine finds love with beauty therapist Donna Tierney. And it's a probably whirlwind romance. Within seven months, he's proposed. Apparently, he books a hotel room. She walks in and he spelled out the word marry me in candles.

39:18That's really romantic. He'd seen that in a wedding magazine. His PA was very busy doing that. just lighting them up there's no way he did that well yeah I think you can pay the hotel maybe it's his long suffering yeah but yeah just called her like some stupid hour K.W.M head over to the hotel and he follows it up with an even more romantic ceremony so in 2022 they tie the knot in a lavish 200 grand wedding ceremony at Clifton House, which is this Berkshire country house, famous one. It's where Meghan stayed the night before the royal wedding. It's the scene of the Profumo scandal, that like famous scandal that rocked English society in the 1960s.

40:06What was that again? A couple of blank looks on your faces. A government minister slept, a government member of the cabinet slept with an escort at Clifton House who turned out to be dating a Russian spy. So it was a sex scandal, but it was actually also like a spying security issue. And I can't remember what happened next but he lost his job. It was a huge establishment scandal. You remember it well. Of course, yeah. 1963, if I had to guess. Cold War paranoia meets fruity 60s shagging. That sounds great. What a time to be alive. Ooh, maybe a movie. You can see why Jermaine Defoe was attracted to that house.

40:43Anyway, the ceremony, gorgeous. We're looking at some of the beautiful pics that were splashed all over OK Magazine. God, roses everywhere. Roses everywhere. He's in white tie, is that? A white jacket. It was a black tie. I don't really know. She's in a lovely dress. Lacy detail on the arm. Is this what people want to hear?

41:06Suddenly we're watching Loose Women. Wonderful texturing, Dan. It's a gorgeous pair of happy couple. But who's she wearing? She's wearing Jermaine Defoe's global brand. You can imagine his PA the night before on the sewing machine with that lace making a corsage. Anyway, sadly, it's all about to turn predictably pear-shaped. So just a month after the ceremony, Jermaine Defoe, OBE, is exposed by the tabloids once again for propositioning a nurse for a shag in his Range Rover. So I think it's not the first nurse we've had in this story. No, he's got a thing. In his Range Rover. Yeah. He wants her to come and shag in the car, which I've never seen the appeal of shagging in cars.

41:59No. I mean, Range Rover, if you've got to do it, then Range Rover's probably more spacious. But like, I guess you've got to be... If you're cheating on someone, I guess you're not doing it in your... Yeah. But you've got to be slightly excited by the idea that you might get caught, I think. Do you know what I mean? It's a bit exhibitionist, but for me, not enough space in there. what's wrong with missionary with socks on and the lights off anyway uh yeah he's he's um he's done once again by the tabloids he's had pretty bad luck with kiss and tails you'd have to say and um that's it the mcdonald calls the marriage off and you know it's pretty sad he's just got married for the first time but fortunately jermaine isn't facing any long drawn out divorce proceedings because it turns out that the entire wedding ceremony was in fact a sham acted out for the hacks at okay magazine after germaine and donna couldn't agree the terms of their prenup so they were going to get married uh but then they couldn't agree their prenup but okay magazine had basically offered them all this cash to get married and have photos in the magazine so they just went through the motions as a wedding so he's not even cheating here.

43:13Well, I mean, he's cheating. They are a couple. They still want to be together, but they're not married. I kind of rate that. They still get to have the fun. They get their big day. Yeah. It's just a fake ceremony, which is, yeah, I quite rate it. And actually, do you think OK magazine? They get their picks. Yeah, if it comes out later, they've flogged their magazines. They're flying off the shelves. Everyone wants to get a pick of the inside scoop on Defoe's weather. The inside scoop. I can't imagine it's great for Donna sort of like, you know, that moment before you walk down the aisle with your dad and it's like he's getting a bit teary I can't believe my little girl's getting hitched and in her head she's like it is a wedding I mean, okay magazine hitch Anyway, so it does make calling it all off a bit simpler and having broken up with Donna Jermaine goes on a shagging rampage, so first off he jets off with this influencer, Alicia who had actually been a guest at the wedding and he'd actually, it turns out, been having an affair with all along.

44:20So besides the nurse he propositioned, he'd been chagging Alicia. I mean, he'd basically been going out with her. So Donna, the one who he was marrying, but didn't marry, if you're still following, she later found some love letters between Jermaine and Alicia, which she posted on Instagram. And the one from Alicia's like, happy birthday, Jermaine. Can't wait to spend the rest of our lives together. And then she rocked up at the wedding. And then she went to his, this world is warped. It's a bit like the Roderick Giggs description. So Alicia is writing letters like that to Jermaine, and then she's going to his wedding, which I guess she knew it was a sham.

44:50And then he's ditching the wedding, and yeah, they're fucking off for a fling. And then at the same time, Defoe also shacks up with a woman called Paige, who happens to be a wedding planner. Which, not his wedding planner. No, not his wedding planner. but just page donna alicia they just sound like names that they're having affairs with people it's just their proper donna is such a sitcom affair name isn't it it's just yeah it's a modern day for weddings i mean in a way you know we we've talked about germaine devoe being a hopeless romantic you can kind of see it with this it's like he wants the big wedding day he wants to be with a wedding planner yeah do you think that's what that's how they they bonded was just we both have a love of, you know, speaking about like, which, which, you know, which car do you dream of having?

45:38The stationery, all of it, the song, the first dance. I kind of see it. He's like, and he's promising these people the world want to spend our lives together. You can sort of picture him like guzzling red wine and indoor chocolates, crying himself to sleep in front of love actually for the 17th time. It's a key part of his global brand. Yeah. Global brand involves being a romantic figure. So yeah, I mean, there's a lot of coverage in the press at this point of him just openly dating both Paige, the wedding planner, and Alicia, the influencer. It's like one day he'll be pictured kissing one, the next day the other.

46:15So I guess they know about each other. And in the end, he decides to take the obvious step, which is inviting both Alicia and Paige to shack up with him in his North London gaff and join his thruple. So we talked about thruples before in this pod because among the proponents are Ronaldinho, who lived with I think at one point three different girlfriends at the same time. Adriano, the Brazilian footballer, he it wasn't technically a throuple, he installed them both in next door rooms in the hotel and didn't tell them about each other. And David Hay, the boxer, who he had a throuple and he actually cycled one member out and cycled a new one in.

46:54It's sort of a crop rotation. Yeah, it's a rotation. It's a bit like a Jermaine Defoe as a footballer. It's like squad rotation. It's like the sugar babes. None of the original line-up remain. Those were still the sugar babes. I'm going to bring on Mido now yeah I don't know there's varying reports about how into it Alicia and Paige were but it doesn't last forever the honeymoon period for the three-way relationship because one year after forming this throuple Jermaine Defoe is papped in a car park I quote from the tabloids enjoying a 20 minute rendezvous with a mystery woman in the back seat of his motor so good that he's finally got it back at her Same car, Range Rover.

47:35According to what the tabloids call an onlooker, which is presumably one of their hacks in camouflage with a long lens hiding in a bin, they said a jacket appeared to have been tied between the two headrests of the front seats. It was all very odd. This is quite Stan Collymore. What, dogging? Dogging. Is it? They met in the car park, right? Yeah, it was sort of like, go past the war memorial, turn off the M62, go past the war memorial, meet me in the car park. but is dogging dogging's when you're shagging publicly and other people are watching and they're pretending to walk a dog right that's where the name comes from I think for it to be dogging people gotta be watching I really okay I thought dogging was just like meeting up for maybe it is I don't know check out our Patreon episode it's all explained there yeah we actually could do quite a good Patreon on dogging yeah we have have we?

48:22Wimbledon oh yeah we went dogging yeah maybe we now need to learn more about the art so what's the jacket do? hiding because I guess they know so they know there's people that just fucking move we don't actually know what they'd be doing in the back of the seat what are you thinking he's stamp collecting they're swapping yeah swapping a penny red trading you go cards yeah yeah you know like football stickers they used to be those meetups swap shops where you'd meet up with people and swap cards he's just in the backseat with her being like got got got need yeah you've got the shiny you've got the Toronto FC shiny the Drake edition yeah I choose to believe it was something really innocent like that.

49:00But I think maybe he's just so used to being followed around by the paps. It's weird. In this day and age, there aren't many footballers who are getting like this level of tabloid scrutiny. Yeah. Especially for like a retired footballer. Yeah. Yeah. It's quite fuck off. I live my life. I'm happy to hypocritically talk about those stories. Yeah. Yeah. That's kind of where we're up to then. I think there's going to be more. All those like post retirement ones. That's like an 18 month, two year period. It's just like bang, bang, bang, bang. I learned he has broken up with, he's no longer with Alicia or Paige.

49:31So he's single. Yeah. Single and ready to mingle. And ready to, yeah. Marry three different women at once. Which I guess brings us nicely to the sort of verdict. I think like good footballer, nice man, a lot of work for charity. Yeah. There's really only one area to focus on, which is like, is he a piece of shit with women or is he a hopeless romantic? Could he be both? Column A, column B kind of thing. Yeah. I mean, I think I don't know I think he is a bit of a hopeless romantic in terms of like he does I think he wants that he believes himself he believes that he wants to you know have this dream wedding this dream life settle down but then when it actually comes to it I think he can't can't resist the lure of I just wonder if he's really sort of obsessed with this global brand thing I'm a bit obsessed now he faked the wedding and he knows that the paps are watching him in the car and I just wonder if it's all kind of he's trying to keep himself that's why you know you said why are the paparazzi following him he's encouraging it you know it's all a part of his if he doesn't have a scandal in the news because he's not shagging four women at once yeah well you think he's calling he's his own I've just seen Jermaine Defoe in a car park of a golf club and he looks it's a heat magazine and his clothes look amazing have you smelled his fragrance yeah I actually quite like that idea it's all a big big there's a conspiracy yeah but I think he is also shagging I think with footballers like the more you talk to people who know them just from like an early age they are surrounded by women throwing themselves at them so they find it quite hard to wean off I was talking to someone connected to a football club who was saying that like the press team you think the job of like the press team at a football club is to like do press you know PR statements and stuff apparently 90 % of it is hiding footballers cheating scandals like every day a footballer's coming to you being like yeah I did this didn't wear a condom apparently they have to lecture they do like workshops being like please wear a condom so it's like it is endemic in the game he's not unusual and it must be hard then to move to the sort of like family man role there's my defence wrong and or not wrong and rating out of 10 we used to do these and this episode feels quite early upshot in some ways just like simple capers I think not very well I need to score 3.5 2.5 Good guy In half his life Bad guy In the other half You wouldn't want Your sister Or mum To date him No But it wouldn't last For a friend So If your friend was like I'm seeing this guy I met on Bumble Jermaine Defoe What do you think?

52:14I'd actually be really keen Yeah Fucking marry him I met this guy In this weird app Called Jermaine Defoe Yeah He's the only one on there I just kept swiping Through pictures in the same flow. Just dick pics and sunlips. And his fragrance. Yeah, I think it's sub five, isn't it? Logan's score. Three and a half feels right. Thanks a lot, Jack. Thank you very much. Come again. Zach, thanks a lot. Thank you. And if you enjoyed that episode and you've got friends who are fans of Neapolitan ice creams or global brands and apps engineered by Spurs legends, then please do share this episode with your friends or any Upshot episode.

52:52It really helps us grow. our global brand. Thanks a lot for listening. We'll see you next time.

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From the publisher

He’s the pint-sized poacher with a naughty streak.
Jermain Defo bonked lapdancers, bit opponents and spiked his teammates with Viagra.
From bogus weddings to back seat rendezvous, meet England's friskiest forward…
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