A Chelsea cult hero was sold to bitter rivals Tottenham without a say over his future
06:00, 19 May 2026
1992: Jason Cundy of Chelsea in action during a match.
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Jason Cundy was a boyhood Chelsea fan and first team player(Image: David Cannon/Allsport)
Former Chelsea defender Jason Cundy was sold to rivals Tottenham after a deal was struck behind his back.
Cundy these days is mainly associated with the Blues, having come through the club's youth system to feature for the senior side between 1988 and 1992. As a lifelong Chelsea supporter, the talkSPORT pundit will undoubtedly be backing the west London outfit when they face Spurs at Stamford Bridge on Tuesday evening.
The fixture marks a pivotal moment for Chelsea, whose season has unravelled, resulting in them slipping out of the European qualification spots. Meanwhile, Spurs are battling against the drop, though three points would secure them a finish above West Ham, relegating the Hammers, while a draw would virtually guarantee it on goal difference.
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Despite the enormous implications of the upcoming Premier League fixture for both London clubs, Cundy's obvious allegiance to Chelsea means one could be excused for forgetting he once played for Spurs.
The centre-back joined Chelsea as a schoolboy and progressed through their academy setup in the mid-1980s, even being named their Young Player of the Year in 1987. He signed his first professional contract with the Blues in 1988 and made his full senior debut for the first team in 1990, before signing a four-and-a-half-year contract in November 1991.
Yet, despite his popularity among the fans, Chelsea conducted secret negotiations in March 1992 to sell him to Spurs for £850,000. Cundy signed for the north Londoners on loan for a few weeks until the end of the 1991/92 season, after which a pre-agreed clause was triggered and the deal was made permanent.
The transfer proved hugely unpopular with the Chelsea faithful as the club sanctioned the move purely for financial gain. Cundy, who had no desire to join Tottenham, was only told on the Monday before the deal was completed on transfer deadline day on the last Thursday of March.
Spurs player Jason Cundy (c) is congratulated by Neil Ruddock (l) Darren Anderton (back) and Justin Edinburgh after scoring a goal from just inside the Ipswich half during an FA Premier League match between Ipswich Town and Tottenham Hotspur at Portman Road on August 30, 1992 in Ipswich, United Kingdom.
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Cundy was sold to Spurs against his will(Image: Mike Hewitt/Allsport/Getty Images/Hulton Archive)
Speaking on Undr The Cosh, Cundy explained: "The reason was financial. It wasn’t a loan. It was how you manipulate the fees because I joined in March and April was the start of the financial year so that transfer wasn’t really a ‘loan’. It helped one of the clubs financially. The deal had already been done."
When asked about his reaction to the news, Cundy said: "My dream was to play for Chelsea. I’d been there since I was 11 and I didn’t want to play for anyone else. I was playing well. But I did hear a rumour, maybe two weeks before, someone did mention something to me about Spurs and I was like, ‘What are you on about? That’s rubbish.’
"We were at a hotel near Heathrow where the training ground was on the Monday before the window closed. [Manager] Ian Porterfield phoned me and said, ‘We’ve had a phone call from Spurs, they made an offer, it’s been accepted. Terry Venables is going to phone you this afternoon.’ That was it.
"I did not expect anything like that. To have this news… I just couldn’t comprehend it. I asked the manager, ‘If I don’t go, will I be stuck in the reserves?’ And he said, ‘Not if I’ve got anything to do with it.’ It’s almost like I had no say. It was so confusing, going from blissfully happy to being thrown into chaos."
Cundy felt let down by his boyhood club for not involving him in the decision-making process, as well as the fact his call with Porterfield lasted merely minutes. In contrast, Venables showed great interest in the player and clearly wanted him at Spurs.
Following his move across London, Cundy managed just 28 appearances for Tottenham. He was sent out on loan to Crystal Palace in 1995 and then both Bristol City and Ipswich Town in 1996, before completing a permanent switch to the Tractor Boys. Cundy retired in 2000 at Portsmouth, following a prolonged battle with injuries.
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