Jason Cundy's public life seems to have one main purpose: to make Jamie O'Hara as miserable and mortified as possible. 

Cundy is, by now, football's biggest wind-up merchant. It is a role he revels in, and one which has brought talkSPORT's Sports Bar show immense popularity on social media.

He is in his element with that ridiculous Ange Postecoglou mask stretched comically over his head, firing wisecracks and shameful stats about Tottenham over at O'Hara, who can only sit with his head in his hands and take the mockery. 

So, how much pleasure does Cundy take in tearing his radio co-pilot to shreds? 

'A huge amount,' he tells Daily Mail Sport. '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.'

There is something relentlessly funny about the Postecoglou mask. Something about the sheer smugness of it, the expressionlessness, as O'Hara sits a metre away having meltdown after meltdown as this warped face just... watches him, unblinking. 

O'Hara couldn't even escape the haunting face at his wedding to Keziah Grubb this year. On one of the biggest days of O'Hara's life, there was Cundy, head wrapped tight in his favourite Postecoglou-themed plaything. 

In the week after our interview, Cundy posts no fewer than eight clips of him ripping into O'Hara's former club Tottenham, who are bottom of the Premier League and winless. In one, he diagnoses the club with 'Spursitis', something nobody in football wants. 

TalkSPORT has often fallen foul of accusations of ragebaiting its listeners too much, but the mask is almost universally loved by its viewers on social media – unless they're Tottenham fans. 

'I came up with the idea to get masked because talkSPORT is so visual,' Cundy says.  '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.

'It's the same mask each time. It absolutely stinks! It's got a weird smell about it. I tell Jamie it's the smell of failure. That's what it stinks of. 

'I did clean it but think it's best to just leave it now, just to do what it does, somehow just let it lie in its own stink, and the worse the mask gets the worse Spurs get.'

Cundy was speaking to Daily Mail Sport on behalf of TENA Men, who were sponsoring the 2026 Prostate United launch event. The 56-year-old is a survivor of testicular cancer, so the issue of men's health is close to his heart.

'I have a voice to speak and spread a message - go and get yourself checked for testicular cancer, or get a PSA check. You have a duty to yourself and your family.' 

He has brought his cancer experience onto the airwaves before, recording a long-form interview with talkSPORT on the subject in 2022, showing a deeper, more sensitive side to his personality than the joker we typically get to hear. 

There is a pitfall in the show's reliance on Spurs being bad: namely, what if the north Londoners start being good? 

Maybe O'Hara would then have the chance to turn the tables on his mate and have a dig at his alma mater Chelsea. 

In any case, Cundy isn't too worried about Tottenham becoming sensations overnight.

'You can't finish 17th, 17th, and go into a new season expecting there to be a huge dramatic change,' he says. 

'Spurs aren't in the big six. Spurs would be in the big six in the Championship if they're not too careful.

'If they carry on being c***, Roberto De Zerbi will get the sack. That's football. That goes for every manager, not just him. But because it's Spurs, history is repeating itself.

'They've signed players that don't score goals: Omar Marmoush scored eight last season, Savio four. Mathys Tel, meh, four. Richarlison's not in the Premier League squad. 

'If you put Erling Haaland up top, he still wouldn't score. They don't create chances.'

Jason Cundy was speaking on behalf of TENA Men, who sponsored the 2026 Prostate United launch event. To find out more about Prostate Cancer UK’s football fundraising challenge visit – prostateunited.prostatecanceruk.org