'I was living my dream at Chelsea – then they sold me to Tottenham behind my back'

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Former Chelsea defender Jason Cundy was sold to bitter rivals Tottenham against his will. Cundy these days is almost entirely associated with the Blues, having come through the club’s academy to represent the first team between 1988 and 1992.

Given he is a boyhood Chelsea supporter, the talkSPORT pundit will undoubtedly be cheering on the west Londoners when they face Spurs at Stamford Bridge on Tuesday night. It marks a crucial game for Chelsea, whose season has unravelled, leading them to drop out of the European qualification spots.

Meanwhile, Spurs are fighting against relegation, though victory would ensure they finish above West Ham , relegating the Hammers, while a draw would all but guarantee it on goal difference . Despite the huge repercussions of the upcoming Premier League clash for both London clubs, Cundy’s clear favouritism towards Chelsea means one could be forgiven for not realising he was once a Spurs player.

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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 being a fan-favourite, Chelsea went behind his back in March 1992 by agreeing a secret deal to sell him to Spurs for £850,000. Cundy joined 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.

It was a hugely unpopular transfer in the eyes of the Chelsea fanbase, with the club merely signing off the deal because they wanted the cash. Cundy, who had no desire to join Tottenham, was only told on the Monday, prior to the transfer deadline day deal on the last Thursday of March.

Speaking on Undr The Cosh , Cundy said: “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.”

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When asked how he took the news, Cundy recalled: “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 hugely let down by his boyhood club for not considering him in their 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.