The England legend admits he wishes he'd chosen Manchester United over Tottenham
Paul Gascoigne admitted he regrets not choosing Manchester United over Tottenham after turning down the Premier League giants in 1988.
The ex-Spurs midfielder spent three seasons in north London, scoring 33 goals and providing nine assists. He made the switch from Newcastle to Tottenham in 1988 in a transfer valued at £2.2million.
However, problems arose when United had matched the identical bid and were eager to bring Gazza to Old Trafford for manager Sir Alex Ferguson. But Gascoigne ultimately had a conversation with former team-mate Chris Waddle, who persuaded him to opt for the capital rather than Manchester.
Speaking to FourFourTwo in 2023, Waddle revealed how his chat with Gazza influenced the midfielder's decision to join him at White Hart Lane. He said: "I went up to the North East one weekend.
"Terry had given me an additional day off and said that if I saw my pal up there, to have a word about him potentially coming to Tottenham, because everyone knew he was leaving Newcastle.
"I got in touch with Gazza and arranged to meet in a pub at midday on the Sunday. He strolled in with his entourage, all his mates. I asked him who he was going to sign for and he replied, 'Manchester United.'
"I said, 'Why don't you come to Spurs?' I told him he could get lost in London and no one would find out half the stuff he'd do.
"If he moved to United, he'd have Alex Ferguson on his case all of the time, along with some senior players. I said Terry Venables was really knowledgeable and would look after him.
"He said, no, he was still off to Manchester United. I said, 'Fair enough' and wished him the best of luck."
Yet Waddle's chat proved more significant than he'd anticipated. He added: "I left the pub, then he came out with his friends shouting, 'Waddler, see you at White Hart Lane on Monday!'
"I thought he was joking around, but when I returned to London on the Tuesday, I was told Gazza had been at the club the previous day and signed a contract."
Although Gascoigne enjoyed success at Spurs, lifting the FA Cup in 1991, he later admitted to Sky News, following his retirement, that joining United might have been a wiser career move.
Reflecting on the possibility of a switch to Old Trafford in 2009, Gascoigne said: "Maybe if I had stayed at Man United I might have still been there.
"I don't know, you just look at these players and the squad of young kids that play, young Rooney that's there, the Neville brothers and Becks, the way he [Ferguson] just brought them on and there are so many.
"It took me six years to get back talking to Sir Alex, I called him from Lazio and asked him would he re-sign us. He was with Eric Cantona and he said he would see what Cantona was going to do but I think everyone knows if you do something to Sir Alex Ferguson the way I did you don't get a second chance."