The 56-year-old former Chelsea defender is on a ‘generational run’, going viral on a near-weekly basis for his antics on talkSPORT
Younger football fans could be forgiven for not having heard of Jason Cundy until a few years ago. A playing career that had so much promise would drift into relative obscurity after his time at Chelsea and Tottenham in the 90s, and he was even forced into early retirement.
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Now, though, he is going viral across social media on a near-weekly basis for his on-air antics. Cundy is a talkSPORT stalwart after more than 20 years with the radio station, but his emergence as a master wind-up merchant has seen his popularity soar.
In fact, the 56-year-old’s ‘generational run’ means there there is an argument he should be sweeping sports broadcasting awards in 2026.
Chelsea, survival & early retirement
Cundy started his career at Chelsea before going on to play for Tottenham, but his playing days were hampered by a series of health problems
While he is now arguably more synonymous with being a broadcaster after more than 20 years in the business, Cundy actually enjoyed a top-level professional playing career that incorporated spells at Chelsea and, ironically, their London rivals Tottenham, whom he now spends a significant chunk of his time tearing into.
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A lifelong Chelsea fan who used to watch the Blues at Stamford Bridge as a boy, the tough-tackling centre-back came through the club’s academy in the 80s, earning their Young Player of the Year award in 1987. He spent four years in the first team in west London before being sold to Spurs in 1992.
Hampered by persistent fitness issues throughout his career, Cundy was forced to be patient for opportunities at White Hart Lane and headed on various loans before permanent spells with Ipswich Town and Portsmouth. It was during his time with the latter that the defender was diagnosed with testicular cancer in early 1997, undergoing surgery to remove one of his testicles and eventually making a full recovery, returning to the pitch later that year.
However, his playing days would be curtailed three years later. In December 2000, aged just 31, he was forced to retire on medical advice following a serious knee injury that he had actually suffered in training when he was still an Ipswich player, with his final appearance coming almost a year prior on Boxing Day 1999.
“I haven’t put my boots on since that game at Swindon,” Cundy said at the time. “I cleaned them after the game, put them in the boot of my car – and they’ve been there ever since. It’s a sad day. I’m now an ex-pro footballer. When I signed as a 17-year-old for Chelsea, I never imagined it would ever come to this.”
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Duck to water
Cundy launched himself straight into a career in broadcasting after being forced to retire early and has now worked with talkSPORT for more than 20 years
But Cundy didn’t dwell on the heartbreak of his early retirement, instead launching himself first into coaching, and then into sports broadcasting almost by accident. His loud-mouthed nature, infectious sense of humour and unmatched ability to wind people up have made him absolutely perfect for talk radio.
Speaking to Martin Tyler on the ‘Joy of Football’ podcast, the former player revealed he was initially invited on talkSPORT for an interview about his experience with testicular cancer in the early 2000s, while he was coaching in Chelsea’s academy. He made such an impression that he was invited back to be a voice on the club he loves after Roman Abramovich’s takeover and Jose Mourinho’s subsequent arrival in 2004.
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Writing in a Reddit ‘ask me anything’ (AMA) in 2025, Cundy said: “I’d got to terms with retiring. I was still a young man. And I went into the academy and coached. And from that moment on, I’m talking about football every single day of my life now.”
Initially, the ex-defender would feature on talkSPORT’s ‘Football First’ programme alongside Ian Danter and Alvin Martin, and would occasionally guest host on ‘Evening Kick-Off’, before becoming a permanent fixture of ‘The Sports Bar’, the show he continues to front today. He also has an enduring connection to Chelsea, commentating for their in-house media.
While he was on holiday in October 2008, Cundy found himself at the centre of a bizarre incident when talkSPORT DJ Andy Goldstein announced on air that the former defender was absent from ‘The Sports Bar’ because he had fallen off a boat on holiday and drowned, with Chelsea fans even laying flowers outside Stamford Bridge the next day.
Goldstein later revealed it was supposed to be a joke, and the radio station was forced to apologise. “It was a silly joke by Andy that backfired,” Cundy said at the time. “My wife got weird texts and someone even changed my Wikipedia page. I’m sorry if people got upset.”
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‘HAAAS ANYONE SEEN…?!’
Cundy’s on-air rapport with Jamie O’Hara – and ability to wind him up – has seen his popularity soar in recent years, as they go viral time and time again
Despite being in the industry for more than 20 years, it feels as though Cundy has only recently come to the fore in football media, and that is undoubtedly courtesy of his on-air chemistry with current ‘Sports Bar’ co-host and fellow ex-Spurs player, Jamie O’Hara. Crucially, the show is livestreamed, making for some sensational social media clips.
The pair make for excellent radio, ribbing both each other and their callers in equal measure with the help of some perfectly-timed sound effects from one of their producers, known as Hairy Al. However, it’s Cundy’s unmatched ability to wind his co-star up and use of a hilarious visual prop that has seen the duo go viral repeatedly in recent years.
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While Tottenham fan O’Hara laments his side’s latest negative result, of which there have been many, Chelsea-supporting Cundy will whip out a mask with former Spurs boss Ange Postecoglou’s face on it, pull it over his head and continue to have a semi-serious discussion with his co-host while it is distorted absurdly and expressionless across his face.
The resulting content is always absolutely hilarious, and the fact Postecoglou was sacked by the Lilywhites more than a year ago makes it even more relentlessly funny. O’Hara simply can’t help himself, and is unfailingly left completely exasperated by the ridiculousness of the situation, the debate already lost.
In the most infamous example of Cundy’s masked antics, a riled-up O’Hara actually stormed out of the talkSPORT studio following Tottenham’s calamitous 5-2 Champions League defeat to Atletico Madrid back in March, during Igor Tudor’s ill-fated interim tenure. Wearing his Postecoglou mask, a clown hat and a oversized bow tie, Cundy kept poking at his fellow pundit until he exploded.
“If we stick with this guy [Tudor], we’re gone. This club is gone. It can’t get any worse,” O’Hara raged. When Cundy responded by saying that Spurs had ‘drawn the second half’, O’Hara lost it: “Stop going on about the second half! Seriously, mate. Seriously, shut up. Honestly… I’m trying not to swear. You’re a professional pundit. You can’t keep saying that.”
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After attempting to compose himself, O’Hara then walked out. The clip has now been viewed 1.4 million times on X (formerly Twitter) alone, and Cundy even wore the mask at O’Hara’s wedding in April.
The 56-year-old’s other go-to bit comes at the top of the show, as he taunts whichever club has had a particularly bad day with shouts of ‘HAS ANYONE SEEN [insert team name]?!’, before he runs through a list of people and things associated with that club, riffing off a famous piece of Norwegian commentary from the 80s, which came after an unlikely victory over England for the Scandinavians. The words “Can you hear me?! Your boys took a hell of a beating!” make up the rest of the incoherent routine. Throw in his signature mask and it is unadulterated chaos.
‘Gift that keeps giving’
Former Chelsea man Cundy has no plans to go easy on O’Hara, but he insists the show and his jokes wouldn’t work without his co-host
Discussing his antics in a recent interview with the Daily Mail, Cundy insisted he has no plans to rein it in. Asked whether he takes pleasure from winding O’Hara up, he said: “A huge amount. I don’t feel for Jamie. Every single game, they lose or manage not to score. Never has the expression ‘the gift that keeps giving’ been more appropriate to Spurs at any other time.”
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Addressing his infamous mask props, he said: “I came up with the idea to get masked because talkSPORT is so visual. I didn’t realise it would take on a whole life of its own. We bought them from South America and we order a new mask every year.
“We bought the Ange mask when he was the manager at Nottingham Forest, and by the time the mask turned up he’d got sacked, so I had to find a role for it. We’ve got a Gary Neville one, an Arne Slot one, and now we’ve got a Jamie Carragher one, that’ll come out soon.”
Speaking about his on-air rapport with O’Hara to The Observer recently, Cundy insisted that his new-found success is very much down to his connection with his co-host. “Without Jamie, it simply wouldn’t work,” he said. “We’re both lucky that we found this chemistry. I could be his dad, but it doesn’t feel like that. We have really similar senses of humour, we both have a similar path – football, going out, ex-wives. It has to be authentic, he’s the perfect foil for me. You couldn’t manufacture that.
“He knows what’s going on, he’s brilliant. I love him dearly. And don’t worry, Chelsea will fall, and he’ll be there for it, and I’ve got to be there for it as well. Jamie will have his day.”
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Generational run
Cundy took on the notoriously difficult Piers Morgan during October’s international break as they clashed over Portugal’s treatment of Cristiano Ronaldo
But this isn’t to say Cundy can’t do serious punditry, too. The former Chelsea man reached new heights during the October international break when he was invited on Piers Morgan’s Sports Uncensored show to debate the fallout of Cristiano Ronaldo’s monumental tantrum after being left on the bench by Portugal.
Morgan claimed Ronaldo had been “lied” to by manager Jorge Jesus following the 41-year-old attacker’s 1,900-word statement on the matter, but Cundy gave that argument short shrift to achieve yet more virality. Responding to Morgan’s defence and pandering to his so-called friend Ronaldo, he said: “Piers, this is not Soccer Aid. We’re talking about elite-level football here. You follow Arsenal, right? You watch [Mikel] Arteta. Can you imagine Arteta promising [Martin] Odegaard to come off the bench? Can you imagine Odegaard doing the same thing?”
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After a dig about ‘elite-level football’, Morgan then sniped back with the claim that Ronaldo was ‘promised’ he could come on, to which Cundy responded: “There’s no promises, it’s a plan. I’ve been in the dressing room. I know what it’s like. Managers have plans. I’ve been in changing rooms on a Friday when the manager’s put the team out on and on Saturday he’s changed it. That’s his prerogative. He is allowed to do that. That’s his job.
“He doesn’t owe Ronaldo anything. His job is to get the best result for Portugal, and if he thinks by not bringing on Cristiano Ronaldo is the best way to get result, that is his job.”
For once, divisive broadcaster Morgan was left without much of a response. The clip has now been viewed close to four million times, and a subsequent tweet stating that Cundy was “on a generational run” has racked up 26,000 likes.
Juggernaut
Cundy has no plans to stop anytime soon and believes other outlets are trying to copy what he and O’Hara have created on ‘The Sports Bar’
At the moment, there really is no stopping the Cundy juggernaut. Something of a late bloomer in the broadcasting world, he has no plans to slow down, in the belief that his and O’Hara’s show – and a format where hilarious moments are clipped up before exploding on social media – is now the envy of the established order.
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“When I first joined, the BBC and Sky would look down their nose at us, now they copy us,” Cundy tells The Observer. “They can’t do it as well as us, but they’re trying to copy what we do.”
He continued: “Look, Roy Keane’s not going to wear a mask. There is a space, and especially in the social media world, where you can have fun and take this and have a laugh in the world. We are so shallow, but I think people do take football too seriously, and we definitely don’t.”
Asked about his future, Cundy said: “I’m thinking how can I still stay in this industry? I absolutely love it. I’m the luckiest guy in the world. I don’t know what the next 10 years look like, but I’d like to think I’ve got a chance to ride whatever’s thrown at me.”
Disclaimer : This story is auto aggregated by a computer programme and has not been created or edited by DOWNTHENEWS. Publisher: Sports.yahoo.com
