The Premier League icon could've become a legend with Manchester United if he'd avoided one simple conversation
Paul Gascoigne admits he wished he'd given Manchester United a shot over Tottenham after snubbing the Premier League giants in 1988.
The former Tottenham man spent three seasons in north London, scoring 33 goals and nine assists. He joined Spurs from Newcastle in 1988 on a deal worth £2.2million at the time.
The only problem was United had also submitted the same offer and were keen on securing Gazza's services for boss Sir Alex Ferguson. However, Gascoigne ended up having a chat with former teammate Chris Waddle who convinced him to move to London over Manchester.
Waddle spoke to FourFourTwo in 2023 and claimed his discussion with Gazza swayed the star to join him at the Lilywhites instead. 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."
However, Waddle's conversation ended up being more important than he thought. 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."
Despite Gazza's success at Spurs, where he won the FA Cup in 1991, he told Sky News years after his retirement that United could've potentially been the better choice for his career.
Discussing the potential of moving 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."