I was told to snub Manchester United and sign for Tottenham – I shouldn’t have listened

Sir Alex Ferguson was in Malta when he read the bad news – a holiday cut short in the worst possible way.

It was the summer of 1988 and Paul Gascoigne had agreed to join Tottenham after Newcastle United’s £2.2million valuation had been met, but they weren’t the first to do so. Manchester United had already put their cash on the table.

“Can I go on holiday knowing that I’ve signed you, Gazza?” Ferguson asked over the phone. The response was an outright yes but this deal was far from done, and it never got done at all.

Ferguson was in his early years as United manager in the late 1980s and was keen to bring in that kind of talent that won matches and titles. It was during a game against Newcastle in 1987 that he first laid eyes on that exact player.

Managed by Willie McFaul, the Magpies had been meandering in the lower half of the First Division but they had a star in their ranks by the name of Paul Gascoigne. The then-20-year-old was famously fuelled by Mars Bars and Newcastle Brown Ale but ran United’s midfield trio of Bryan Robson, Norman Whiteside and Remi Moses ragged.

Admittedly, no one in that era was a model of physical fitness but Gascoigne did things to that United midfield that few had done before. Ferguson set his sights on the midfielder who would go on to be crowned PFA Young Player of the Year and listed in the PFA Team of the Year that season.

Such was Ferguson’s desire to sign Gascoigne that he spoke to the mercurial midfielder himself, selling the United project. And he had worked his magic, the pair agreeing a deal will be formalised and Ferguson could head on his summer holidays.

After agreeing what looked to be the move of his dreams, Gascoigne took the summer to unwind back in his hometown, catching up with old friends before heading south to Manchester. It was during that time that he went for a drink with then-Tottenham man Chris Waddle.

“I went up to the North East one weekend,” Waddle told FourFourTwo recently. “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.”

Gascoigne may not have made his mind up that day but his chat with Waddle certainly planted a seed of doubt. The midfielder was on his way to Old Trafford when then-Tottenham chairman Irving Scholar called.

In what is now an infamous series of events, Scholar attempted to woo Gascoigne with several add-ons, including a house for his family, a white BMW for his dad and even a sunbed for his sister. And so the in-demand midfielder swerved away from Manchester and headed down to London.

Ferguson wrote a letter to Gascoigne in fury, lamenting the Geordie boy for turning down the biggest club in the world and labelling him a ‘silly boy’. The Reds boss had been crossed and that is not taken lightly.

Gascoigne’s scintillating form over the following two campaigns would earn him a place in Sir Bobby Robson’s squad for Italia ’90, where he would become a household name across the country. Upon returning, he helped Tottenham reach the 1990/1991 FA Cup final but in the first of many cruel twists, he tore knee ligaments in a reckless challenge and was taken off in a stretcher.

The England star missed out on regular football – his only true release – for over a year and that, coupled with his growing public image and the scrutiny that came with it, led to off-field issues. Gascoigne has been open about previous issues with alcohol and drugs, and found himself in undesirable circles during his three years at Lazio.

Gascoigne became almost unmanageable in Italy but one person who could have kept him on the straight and narrow was Ferguson. It was a huge regret of the eccentric playmaker, who believes he could have followed the path of other England stars who played under the Scot.

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

The paths of both Ferguson and Gascoigne suggest it would be the latter who harbours regret. United went on to enjoy unprecedented success with their new manager, dominating the Premier League era and adding a couple of Champions League trophies to boot.

But it’s hard not to imagine what the United side of the early 1990s – that of Cantona, David Beckham, Ryan Giggs and Andy Cole – might have achieved with a Gascoigne thrown in there as well. As much as anything, it would have been one of Ferguson’s biggest tests in management, and a hugely rewarding one had he got it right.

“In reality, you have to say, there’s only one that always comes to my mind and that’s Gascoigne,” Ferguson told the UTD Podcast when asked which signing he regrets missing out on. “He was absolutely fantastic. I think if we’d have got him, he would have had a great career, I really do.”