I shouldn’t have listened when I was encouraged to sign with Tottenham instead of Manchester United.

In 1988, Paul Gascoigne was the most sought-after player on the transfer market, but he had an abrupt change of heart after sending Sir Alex Ferguson on vacation with an agreement to join Manchester United.

When Sir Alex Ferguson received the unfortunate news of his vacation being abruptly ended, he was on Malta.

In the summer of 1988, Newcastle United had fulfilled their £2.2 million valuation and Paul Gascoigne had agreed to join Tottenham,

although they weren’t the first to do so. Manchester United has already made a financial commitment.

“Gezza, now that I’ve signed you, can I go on vacation?” Ferguson called and inquired.

The answer was a resounding yes, but the agreement was never really completed and remained unfinished.

When Ferguson first took over as manager of United in the late 1980s,

he was eager to bring in players who could win games and championships.

He saw that same player for the first time in 1987 during a match against Newcastle.

Under the direction of Willie McFaul, the Magpies were circling around the bottom half of the First Division,

but they did have a great player in Paul Gascoigne.

The 20-year-old, who was renowned for being sustained by Mars Bars and Newcastle Brown Ale, outplayed United’s midfield trio of Remi Moses, Bryan Robson,

and Norman Whiteside.

Although it’s true that nobody was particularly physically fit at that era,

Gascoigne accomplished feats with the United midfield that very few had before.

Ferguson focused on the midfield player who ended up winning the PFA Young Player of the Year award and being named to the PFA Team of the Year for that particular season.

Ferguson was so keen to sign Gascoigne that he personally chatted with the erratic midfield player, pitching the United project to him.

And he had done his magic; the two agreed that a formal agreement would be reached, allowing Ferguson to take his summer vacation.

Following his agreement to what appeared to be the transfer of his dreams,

Gascoigne relaxed in his hometown throughout the summer, visiting with old acquaintances before moving to Manchester in the south.

He had a drink with Chris Waddle, a Tottenham man at the time, during that period.

“I spent a weekend in the North East,” Waddle recently said to FourFourTwo.

Terry granted me an extra day off and instructed me to speak with my friend in the area if I saw him,

as it was widely known that he was leaving Newcastle for Tottenham.

“I made plans to see Gazza in a pub on Sunday at noon after reaching out to him.

He entered with his group of friends in tow. When I asked him who he intended to sign with, he said, “Manchester United.” “Why don’t you come to Spurs?” I asked.

I assured him that nobody would discover half of the things he would do if he got lost in London.

He would always have Alex Ferguson and a few experienced players on his side if he moved to United.

I told him Terry Venables would take care of him since he was very knowledgeable.

“No, he was still going to Manchester United,” he replied. “Fair enough,” I replied, and I wished him success.

After I left the bar, he and his pals emerged and yelled, “Waddler, see you at White Hart Lane on Monday!”

I assumed he was kidding, but on Tuesday when I got back to London,

I found out Gazza had actually signed a contract at the club the day before.”

Although Gascoigne may not have made up his mind that day, his conversation with Waddle undoubtedly sow doubt.

When former Tottenham chairman Irving Scholar contacted, the midfield player was en route to Old Trafford.

Scholar tried to court Gascoigne with a number of perks in what is now a notorious chain of events, such as a house for his family,

a white BMW for his father, and even a sunbed for his sister. Thus, the highly sought-after midfield player diverted from Manchester and made his way to London.

Enraged, Ferguson sent a letter to Gascoigne bemoaning the Geordie youngster’s rejection from the world’s largest club and calling him a’silly boy’.

It was not taken lightly that the Reds boss had been betrayed.

With his brilliant play over the next two years, Gascoigne earned a spot in Sir Bobby Robson’s side for Italia ’90,

a tournament that would make him a national celebrity. After making a comeback, he supported Tottenham to the FA Cup final in 1990–1991; however, in the first of many tragic turns, a careless challenge caused him to tear his knee ligaments, and he had to be removed on a stretcher.

The England player experienced off-field problems as a result of missing out on regular football,

which was his only genuine release, for more than a year. He also experienced criticism due to his rising public persona. Gascoigne, who spent his three years at Lazio in unpleasant circles, has been upfront about his past struggles with drugs and alcohol.

In Italy, Gascoigne became nearly uncontrollable; nonetheless, Ferguson was someone who may have held him in check.

The eccentric playwright regrets it deeply, feeling he could have gone on to become as successful in England as other talents who trained under the Scot.

In 2009, Gascoigne told Sky News, “Maybe if I had stayed at Man United I might have still been there.”

“I’m not sure, but just take a look at these players and the group of young players—you see young Rooney playing, the Neville brothers, Becks—and how Ferguson [the manager] just brought them all on and there are so many.

It took me six years to contact Sir Alex again. I requested him to re-sign us over the phone when I was in Lazio. When he was with Eric Cantona, he said,

“I think everyone knows you don’t get a second chance if you do something to Sir Alex Ferguson the way I did.” However, he would watch what Cantona did.

Given their respective trajectories, it appears that Gascoigne is the one who is harboring regret.

With their new management, United continued to have unheard-of success, dominating the Premier League period and taking home a few of Champions League championships as well.

However, it’s difficult to ignore the possibilities of what the United team of the early 1990s, which included Gascoigne in addition to Cantona,

David Beckham, Ryan Giggs, and Andy Cole, may have accomplished. More than anything, if Ferguson had done it correctly,

it would have been one of his greatest management challenges and extremely rewarding.

Ferguson responded to the UTD Podcast when asked which signing he regretted missing out on.

“In reality, you have to say, there’s only one that always comes to my mind and that’s Gascoigne,” Ferguson said.

“He was outstanding. I genuinely believe he would have had a fantastic career if we had acquired him.”

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