Sir Alex Ferguson suffered one of his greatest career setbacks when Paul Gascoigne reneged on a promise to sign for Manchester United, instead opting for a move to Tottenham in 1988.
The legendary Scotsman had an agreement in place with the mercurial talent, even asking him during a call, "Can I go on holiday, knowing that I've signed you Gazza?"
A confident 'yes' from Gascoigne sealed what seemed like a done deal, but it all fell through.
Ferguson, at the dawn of his Old Trafford dynasty, saw Gazza's potential to be a game-changer during a First Division game in 1987, despite Newcastle's poor display under Willie McFaul. The energetic 20-year-old dazzled against seasoned pros like Bryan Robson and Norman Whiteside, a feat that few could claim.
Gascoigne's football prowess was undeniable as he earned the PFA Young Player of the Year title and a spot on the PFA Team of the Year.
According to the Manchester Evening News, Ferguson reportedly phoned Gascoigne personally, selling the United vision, and was successful in persuading the midfielder to agree to a transfer. Ferguson was so convinced that he had secured Gascoigne's signature that he went on holiday, expecting the formalities to be completed upon his return.
In the meantime, Gascoigne returned to his hometown, where he spent time with friends. One of these friends was Chris Waddle, who played for Tottenham at the time.
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Waddle had been instructed by his manager, Terry Venables, to persuade Gascoigne to join Spurs if he saw him during his visit to the North East. Waddle recounted the events in an interview with FourFourTwo: "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. 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."
The midfielder was en route to Old Trafford when he received a call from Spurs chairman Irving Scholar, who enticed him with various perks, including a house for his family, a white BMW for his dad, and even a sunbed for his sister. This led to Gascoigne diverting his journey to London instead.
Ferguson expressed his disappointment in a letter to Gascoigne, calling him a 'silly boy' for rejecting the world's biggest club. Despite this setback, Gascoigne's impressive performances over the next two seasons earned him a place in Sir Bobby Robson's squad for Italia '90, where he became a national sensation.
Upon his return, he helped Tottenham reach the 1990/1991 FA Cup final. However, a knee ligament injury sustained in a reckless challenge saw him stretchered off the pitch, marking a tragic end to his season.
The England sensation opened up about the agony of being kept from football, his salvation, for more than a year. Amidst escalating fame and intense public scrutiny, off-pitch woes began to multiply.
Gascoigne has never shied away from discussing his former demons with alcohol and drug abuse—issues that intensified during a troubled three-year spell with Lazio. In Italy, where Gascoigne's behaviour often spiralled, it seemed only one man might have reined him in: Ferguson.
The talented midfielder laments the missed chance to be under Ferguson's tutelage at Manchester United, convinced he could have emulated other illustrious England players moulded by the legendary Scottish manager. "Maybe if I had stayed at Man United I might have still been there," Gascoigne reflected during a 2009 Sky News interview.
"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."
Ultimately, it appears that among Ferguson, forever associated with United's golden era laden with Premier League crowns and Champions League victories, and Gascoigne, the one left with lingering remorse is the player, not the celebrated gaffer.
It's intriguing to consider what could have been if the Manchester United team of the early 1990s, featuring stars like Cantona, Beckham, Giggs, and Cole, had also included a talent like Gascoigne. It would have undoubtedly presented Ferguson with one of his greatest managerial challenges, and a highly rewarding one if he had succeeded.
"In reality, you have to say, there's only one that always comes to my mind and that's Gascoigne," Ferguson revealed on the UTD Podcast when asked about the one signing that got away. "He was absolutely fantastic. I think if we'd have got him, he would have had a great career, I really do."
