Tottenham, the Alan Sugar years (2024)

“It made me a very cynical person,” Lord Alan Sugar tells The Athletic. “I was a joking, happy-go-lucky fella before I got into football but unfortunately being in football, you’ve got this defensive wall around you.”

For many of you reading this, to think of Lord Sugar is to think of the gruff boss onThe Apprentice.For those of you reading this in America, yes, that kind of makes him our equivalent of President Trump.

But before all of that, Lord Sugar was the Tottenham Hotspur chairman — with this month marking 20 years since he sold the club to Daniel Levy’s ENIC. And having taken over in 1991, it was a decade of staggering turbulence for Tottenham.

At the start of the 1990s, Tottenham were certainly not the best team in the country, but they were the most exciting. Managed by Terry Venables, formerly of Barcelona, starring England’s finest, Gary Lineker and Paul Gascoigne, owned by stylish property developer Irving Scholar, they had a glamour that their better-run rivals could not match.

And in the summer of 1991, after Spurs had won the FA Cup, Daily Mirror owner Robert Maxwell tried to buy the club from Scholar. But it was not Scholar, Venables, Maxwell, Gascoigne or Lineker who defined Tottenham in the 1990s.

The 1990s at Tottenham will always be about Alan Sugar, the man who rescued the club from the brink of bankruptcy, stabilised the finances, fought and won a civil war with Venables, nearly brought in a thrilling new era of foreign superstars, lurched between unpopular managerial appointments and then eventually sold up, exhausted, to a 38-year-old Levy in 2000.

Sugar was never popular with the Tottenham fans, who took Venables’ side against him, who demanded he spend more money, and who never forgave the appointment of Arsenal legend George Graham. But Sugar’s legacy deserves a second thought. The club that he sold to ENIC was in a far healthier, stronger state than the one he bought from Scholar in 1991. And none of the progress under Levy — the stadium, the training ground, the Mauricio Pochettino era — would have been possible without Sugar guiding the club through the transition of the 1990s.

So, 20 years on, how do Sugar and those involved with the club at the time reflect on his time in charge. A period of stabilisation or stagnation? Was the club rescued from oblivion?

The Athletic has spoken to Sugar himself, the man he sent in to fix Tottenham’s operations Claude Littner (another you may recognise from The Apprentice), and a host of players, managers, coaches, executives and supporters from the period.

What we discovered was a period that continues to divide and surprise. A story of constant conflict and agitation, of giving Graham “absolute hell”, of telling Teddy Sheringham to “sod off” to Manchester United and being accused of “f*cking bullsh*t” by Darren Anderton.

Or as Sugar put it when asking Littner to go in and troubleshoot: “It’s like World War III there. Just go in and sort it out.”

To understand why Sugar’s reign was so valuable to Tottenham, you have to go back to the state of the club in 1990-91. Venables’ team was thrilling, but it disguised a financial crisis that put the survival of the club at risk. The finances needed some attention after expensive stadium renovations. They had to sell Chris Waddle to Marseille in 1989 for £4.5 million. Two years later, they had to do a deal to sell Gascoigne to Lazio for £8.5 million, a huge fee for the time, but one Spurs never got in full because of his knee injury. The club considered a sale and leaseback deal for White Hart Lane. And Scholar and Paul Bobroff were looking for a buyer.

This was 1991, before the foundation of the Premier League, and long before the days when being a big club meant you made money. So who would want to buy an asset like this? There was plenty of early talk about Maxwell, but Sugar, a 44-year-old Tottenham fan who had made his money in property and consumer electronics, wanted to head off the controversial media magnate, who was trying at the same time to sell Derby County.

On Friday, June 21, 1991, Sugar arrived at the office of merchant bank Ansbacher to complete the deal for Scholar and Bobroff’s shares. But Maxwell had sent a team of his employees to the office to interfere and called Sugar to put him off.

“I remember having a phone call with him,” says Lord Sugar, 29 years on. “I said: ‘Mr Maxwell, I don’t think you’ve got any money’. And he went mad. I said: ‘It’s all very well wanting to be a passive investor and all that rubbish, but we’re in the completion meeting here today. I’ve got a paid banker’s draft ready to do this deal, you’ve sent an army of idiots. And quite frankly I don’t think you’ve got any money!’”

Sugar won the battle, persuading Scholar and Bobroff to sell their shares. But it was not only Sugar who was part of the new consortium. Seeking extra backing for his bid to save the club, Sugar had enlisted Venables, who had been Spurs manager since he replaced David Pleat in 1987. Venables, at this point, was simply a far bigger figure than Sugar. He was the man who did so well at Queens Park Rangers, taking them to the FA Cup final and qualifying for Europe, then he left Loftus Road in 1984 for Barcelona, where he won one Spanish title and reached the 1986 European Cup final.

Venables was a big football figure, but a man bigger than football too. He co-wrote the James Hazell detective novels and owned Scribes West, a drinking den for the rich and famous in Kensington, west London. Venables brought football knowledge, credibility with the press, popularity with the fans and an equal £3 million investment with Sugar.

But Sugar was taking a risk by going into business with Venables. “I remember saying to Alan that when you look at the figures at Spurs, it was a basket case,” says Colin Sandy, who advised Sugar and was appointed as finance director to the Spurs board in 1991. “So what you were actually investing in was Terry Venables. And the belief in him being all that he said he could do. The theory was, when we turned up the day after doing the deal at Ansbachers, to do the press thing at the ground, that it looked like a partnership made in heaven.”

The saying at the time was that Venables, as chief executive would look after the ‘11 on the pitch’, while Sugar, the chairman of the PLC would ‘look after the £11 million at the bank’, a reference to the club’s overdraft. But the club’s financial problems in that first year went deeper than that, with a daily scramble to pay all of the mounting bills and debts. “Money would come in every day, and we would sit down and decide who was going to be paid,“ Sandy says. ”When I arrived at the ground every day, I was met with a pile of payments to be made, and I’d spend the next hour or so signing cheques.”

Everyone did get paid, both in the Scholar and the Sugar and Venables eras. “Normally when a company is in financial difficulty salaries and bills are left unpaid and writs are served for non payment,” Scholar says. “Not a single writ or solicitors letter was served and nobody’s salary or bill was not paid in full and on time.” As Sandy says, “it needed careful management to get out of it.”

Careful management was difficult, though, when the club was being pulled in two different directions. Sugar was working hard behind the scenes to fix the finances, while Venables was the public face of the club, bringing former manager Peter Shreeves back in to work underneath him. After the creation of the Premier League in 1992, it was Venables who would attend the chairmen’s meetings, networking with David Dein, Martin Edwards and Peter Swales. Venables and his associates would get the best seats in the directors’ box, and the fans at White Hart Lane, still loyal to their former player and manager, would still sing “Terry Venables’ Blue and White Army”.

Behind the scenes, cracks were starting to develop. Sugar’s desire for financial control was clashing with Venables’ freewheeling approach. When Sugar was on a summer holiday in Sardinia in August 1991, Venables signed Gordon Durie from Chelsea, despite Sugar’s insistence that no-one could be bought without his permission. “That was a surprise,” says Sandy. “We were pacifying the bank, and Alan was putting his own money in. And then we suddenly get these pieces of expenditure we had no idea was coming. That made life very difficult for Alan because he likes to know what’s going on.” Soon after, Venables signed Jason Cundy from Chelsea as well.

“[Sugar] would look after the business side of the club while my responsibility was the football,” Venables wrote in his autobiography Born to Manage. “Football was my side of the business, which included selling and buying of players,” he added.

“I found him very much a dominant figure, again no crime but an irritant,” Venables goes on to say. “I can only think where it went wrong between us…. was his apparent inability to share control with me. He was used to being in sole charge.”

The sad fact of Tottenham in the early 1990s is that this battle, between Sugar and Venables, overshadowed anything that happened on the pitch. As one senior insider puts it, the best model of football ownership involves separating the power and the glory, but at Tottenham, that distinction was blurred. And there was a personality clash too between the out-sized celebrity manager — who looked like the senior partner — and Sugar, the hard-working businessman. “Alan is very precise, solid, figures-driven, he likes to do things in the right way, from every angle,” says Sandy. “That’s just the way he is. And Terry was not of the same mould. I had difficulties with him. There was a clash of cultures, I suppose.”

While Sugar and Sandy worked to fix the finances of the club, they saw Venables as more interested in an easy life. “He was supposed to run the football side, but he seemed to delegate a lot of it,” Sandy says. “He wasn’t as hands-on as we thought he was going to be.” Venables appointed men such as his personal assistant Eddie Ashby, an undischarged bankrupt who Sugar could never fully trust. As things got worse between Sugar and Venables, Ashby was eventually dismissed in May 1993.

Looking back, Sugar regrets going into business with Venables and allowing his business partner to make so many appointments at the club. “They all seemedrather nice people, in awe of Terry, and most of them were up his arse, and he loved that. He loved that, people running around him.”

As for whether he was too trusting, Lord Sugar says: “I suppose there was a bit of naivety, as far as I was concerned. I look back and kick myself that I didn’t perform any of the due diligence on acquiring the business.

“I think I blindly moved into it,” he adds. “Because of the passion towards the club. Obviously, it was a very bad mistake. We entered into an era of litigation for about two or three years.”

It was soon clear that Tottenham was big enough for one of Sugar and Venables, but not both. Club employees found themselves torn between the two men. And eventually, at the end of the 1992-93 season, Sugar had to make his move. The club could not afford another season of internal warfare. So on May 13, 1993, Sugar and his legal team put a resolution to the board to remove Venables from his £250,000 per year job as chief executive, ending his six-year spell at the club. The resolution passed. Ted Buxton, Spurs’ chief scout, said it was “the worst day in the club’s history” as “Terry is the best man in the world for the job”.

Many of the players were on Venables’ side as well. He had signed or managed almost all of them. Even after Venables moved upstairs in 1991, he had continued to have a hands-on role on the football side, working through first Shreeves and then Doug Livermore and Ray Clemence the following season. To the players, Venables was always their man in a way that Sugar could never be. Gascoigne said that Spurs should be renamed “Tottenham Venables” in honour of “everything Terry has done for the club”.

Darren Anderton had been signed for £1.75 million by Venables in 1992 and felt a sense of loyalty to him. “Terry had brought me to the club as a 20-year-old, so I was gutted,” Anderton recalls. “I just remember being absolutely gutted at the news, and just didn’t think it was real. My first reaction was anger, and just fuming.” Neil Ruddock said that he had torn down his Amstrad satellite dish and put it in the bin. His then-wife Sarah protested outside Sugar’s home in Chigwell, with a placard saying ‘WE WANT T, NO SUGAR’.

The fans were just as supportive of Venables. After his lawyers won a temporary injunction against his dismissal, this set up a showdown in the High Court on June 10, Venables v Sugar, a day that would shape Spurs’ modern history. And Venables still had the support of many Spurs fans, who travelled to the court as if it were an away game, singing their support for their hero and their antipathy towards Sugar. Many of them made it into the public gallery and had to be told to be quiet by the judge during the hearing.

But the fans were powerless to stop Sugar from winning — he simply was on much better ground legally — and the dismissal of Venables was upheld. Sugar and his team had to scramble fast out of the court, racing out of the back door, through the judge’s chambers, into a waiting taxi to take them all away from the waiting photographers. But they had won.

Sugar finally had the power to control Tottenham Hotspur. But that power came at a price. Having got rid of the beloved Venables, Sugar was hated by many fans and players. “I feel like the man who shot Bambi,” he admitted at the time.

But in the summer of 1993, two years after the initial acquisition, Sugar finally had the chance to put his own stamp on the club with two key appointments. On the pitch, Sugar’s first real managerial appointment, he went for Ossie Ardiles, the legendary former Spurs midfielder.

Off the pitch, Sugar wanted someone new to help him to control costs. Littner had been working as a troubleshooter for Sugar’s companies around the world and had been promised a new job as Amstrad chief executive. But then Sugar called him and told him he had something much bigger in mind: running Spurs. Littner had been a Spurs fan all his life, but he was reluctant. Sugar was insistent. “Look Claude, you’re the best person, you’re the only person to do it,” Sugar told Littner. “Please, it’s like World War III there. Just go in and sort it out.”

Littner had made his name as a “turnaround expert” working for Sugar, but what he found at White Hart Lane in October 1993 was another level. “When I came to Tottenham, I realised that there were loads and loads of problems, loads of different factions,” Littner says. “There was a lot to do, and it was pretty chaotic. And there was no real long-term strategy of how I was going to tackle it. It was like the Wild West there. Everyone was doing their own thing. We had this fantastic, wonderful franchise, but under the surface, we weren’t making the best of what we had.”

Even though Tottenham were one of the most popular clubs in the country, Sugar and his team had to work hard to monetise that popularity. Spurs would fill White Hart Lane with 36,000 fans on a Saturday, but on a Monday, the money simply was not there in the takings. “We had cash turnstiles,” Littner says. “Unfortunately, these were in the family of the stilemen (people who work in the turnstiles) for years and years, and one way or another we didn’t get all the money coming into the ticket office. The numbers just didn’t add up. From the next season, we went all-ticket. Of course, that went down like a lead balloon with the people whose livelihood it was. It was very, very tough.”

The other thing Littner had to do was cut costs. On his first day at White Hart Lane, Littner almost stumbled over the crates of milk left outside the main entrance, crates that stayed there all day. The next day, even more milk was stacked up waiting to be drunk, and the next day after that. Baffled, Littner asked why this was and was told that the players wanted milk delivered to the ground in case they trained there, rather than at Mill Hill. Littner asked whether manager Ardiles might tell club staff in advance where the players would train, so they would not order milk they did not need. He was told that would not be possible either. So Littner cancelled the crates of milk and told club staff to go and get some from the local Tesco whenever the players trained at White Hart Lane.

When Spurs lost their next game, the pro-Venables anti-Sugar forces had a field day. The tabloids ran with stories blaming it on Littner taking the milk away, and he realised just how difficult it would be in that hostile media climate. “With a normal company, you can do more or less what you want without being under the glare of the newspapers,” Littner says. “Here, when anybody said anything, it immediately got into the newspapers. It was always putting a negative slant on us, making us look bad.”

But at the same time, the cost-cutting approach did upset people. Perryman, who was Ardiles’ assistant, saw the ending of the daily milk as a departure from Spurs’ traditions. Perryman has also claimed that bottled water stopped being provided on the team coach, which Littner vehemently denies. This was a club that always used to do things the right way.

“Everything I was taught that Tottenham Hotspur stood for was just knocked down every day I was in there,” Perryman says. “What Tottenham Hotspur stood for in my day was not being adhered to, it was a completely different club.”

The situation was extremely delicate, then, as Sugar and Ardiles tried to relaunch the team for a new era. The players liked Ardiles, who came in trying to play a style of play never seen before in English football. “As soon as the ball goes to Teddy Sheringham,” Ardiles told the players in his first meeting as manager, “everyone fly forward”. In Ardiles’ first season, Spurs finished 15th.

But Sugar’s attempts to move Tottenham on from the pain of his civil war with Venables proved to be very difficult. There was a Football Association investigation into the club regarding secret undeclared payments to players, long before Sugar and Venables even bought a stake. But in June 1994 the FA came down hard on Spurs: they were kicked out of the FA Cup, given a 12-point deduction and a £900,000 fine. “It was a horrible time,” Sugar looks back. That could have killed off his tenure, but he fought back.

Inspired by the sense of grievance to turn things around, Sugar went on a spending spree. That summer, with Spurs facing disaster, Sugar signed Jurgen Klinsmann for £2 million, doing the deal on Sugar’s yacht in Monaco. It was a glamorous flourish that Venables himself would be proud of. Ilie Dumitrescu came in for £2.6 million from Steaua Bucharest and Gheorghe Popescu from PSV Eindhoven for £2.9 million. It is worth restating here how thrilling and new this was in English football in the mid-90s. These players had all starred at the 1994 World Cup — Klinsmann had also won Italia ‘90 with West Germany — and now they were all playing for Tottenham.

In the first few weeks of the 1994-95 season, it felt as if Sugar and Ardiles had torn up everything people knew about the English game. Spurs were ripping opponents to pieces, Ardiles playing an attacking, expansive 4-4-2, with Sheringham and Klinsmann up front, Nick Barmby as a 10, with Dumitrescu and Anderton either side. When Tottenham beat Ipswich Town 3-1, some thought they were going to win the league.

But it did not last. Results soon turned, and Ardiles’ brave experiment collapsed like a house of cards. After a 3-0 defeat at Notts County in the Coca-Cola Cup, the fans called for Ardiles’ sacking, and Sugar gave them what they wanted. The great experiment was over, just 12 league games into the season. Spurs were still looking for their post-Venables identity, and Ardiles left calling it the “impossible job”. The legacy of 1993 still hung over the club.

“Impossible because of the bad feeling towards getting rid of Venables,” says Perryman. “And rightly so because he was a great coach and everything that went with it. The fallout was such that there was a bad feeling all the time. It wasn’t to Ossie or to me. They felt Terry was poorly done by.”

If that was a hard moment for the club, it was quickly followed by a big win. Sugar was determined to fight the FA’s punishment from the summer. So he threatened to take it to court, unless it agreed to let an appeal be determined by arbitration. In November 1994, the arbitrator decided that the FA had acted unreasonably and gone too far. Spurs had their points reinstated and were let back into the FA Cup. “It was a hard thing to do, but we did it in the end,” Sugar looks back. “Graham Kelly was weak as piss in the end, absolutely, he had to give in. I threatened to sue them, and no one had ever sued the FA before. I was fed up of these people.”

With the FA Cup ban overturned and Spurs rebuilding effectively under Gerry Francis, the summer’s feel-good factor briefly returned. Tottenham finished seventh in the Premier League in 1994-95, and beat Liverpool at Anfield to reach the FA Cup semi-final.

Typically for the Sugar era, though, there was a dramatic plot twist waiting just around the corner. Fresh from a thrilling 29-goal season that won him the Football Writers’ Association Player of the Year award, Klinsmann wanted to leave.

And maddeningly for Sugar, there was nothing he could do about it. In Klinsmann’s contract, a clause stipulated that Spurs had to accept a bid if it matched what they had paid the previous summer. “I think I got played a bit there,” Sugar says. “I resurrected his career.”

Sugar was incandescent, and when presented with Klinsmann’s shirt during a BBC interview, supposedly as a leaving present from the striker, he threw it back at the reporter and said he could wash his car with it for all he cared. Klinsmann called Sugar “a man without honour”.

Francis similarly felt the chairman’s ire. “Our biggest row was when I made Klinsmann captain for his last game,” he says. “Alan wasn’t happy because of all the problems he had with Jurgen leaving.

“I said, ‘You’re the chairman, I’m the manager. I say what happens and that’s it. Don’t ever question me on that again’. But it was very frustrating. Klinsmann left, Popescu went to Barcelona.”

After the 1994 transfer splurge and encouraging season, Spurs appeared to be heading back to square one. When it emerged that star midfielder Anderton might also be leaving, Sugar took decisive action.

In one of the more extraordinary stories from Sugar’s time at the helm, a release clause was again the root of the problem. Anderton was an England regular and with Andy Cole having joined Manchester United that January for £7 million, the £4 million release clause was well below the midfielder’s value. More to the point, Anderton was absolutely not for sale.

Word got out about the clause and suddenly Manchester United were sniffing around. Anderton takes up the story. “I remember at the end of that season playing for England in the Umbro Cup (an international friendly tournament),” he says, laughing as he remembers the absurdity of the situation. “I spoke to (Manchester United defender) Gary Pallister, and he gave me a bit of a nudge saying Sir Alex Ferguson wanted me.”

Anderton had been planning to head off to America with his mates for a holiday once the Umbro Cup finished, but was instead summoned from Wembley after the final game against Brazil to Sugar’s house.

Sugar told Anderton how desperate the club was to keep him. Anderton said his desire was to stay too, as long as it was on appropriate terms.

He left Sugar’s Chigwell mansion and went on holiday. While Anderton was away, Ferguson said publicly that the winger was his main summer target. By the time he returned, Ferguson called him at home and explained that United were looking to sell Andrei Kanchelskis and would Anderton come up to Manchester to meet him and have a look around?

Anderton said he was happy where he was but could head north for a chat. United had just been pipped to the title by Blackburn but having won the title the previous two seasons, were very much still the Premier League’s pre-eminent team.

Sugar got wind of what was happening. “The next day he calls me and says come to my house,” Anderton recalls. “Jurgen had gone, and so the thought of me leaving on top of that…”

Anderton recalls Sugar launching a charm offensive to ensure would stay at Spurs. He offered him a lucrative long-term contract with terms that ensured Anderton would always remain one of the club’s highest earners.

Sugar also laid on the sort of lavish hospitality provided for teams that have just won a task on The Apprentice.

“He put on a lovely lunch for us,” Anderton says. “With all the butlers here, there and everywhere. I went in thinking I wanted to stay and it was a ridiculous offer, but if I’d gone up to Manchester it would have been a bit different.

“I remember him popping open a bottle of champagne after we’d agreed it all. The only time he got the hump was when we were in the lounge and I asked if he could throw a car in as well. Because when I first went there they gave me a new BMW. He said, ‘No we don’t do that anymore’, and pointed to his grandson’s toy car and was like, ‘There you go, take that if you want, that’s all you’re getting’.”

Sugar was delighted with the afternoon’s work and with typical attention-grabbing gusto called a press conference to announce Anderton’s new contract.

But the nature of running a football club means that no sooner has one problem been solved than another one pops up. After signing his new contract, Anderton suffered an injury-plagued few seasons, interspersed with starring for England at Euro ’96 and the 1998 World Cup. Anderton feels Sugar was probably frustrated by a feeling of not getting his money’s worth from the midfielder in those years. It led to rows.

The most explosive came a few years later in 1999 when Anderton suffered a nasty achilles injury during training that kept him out for more than four months. On the instruction of the manager Graham, Anderton left training by a different exit to avoid the press. The next day, however, he woke up to discover that news of the injury had been leaked. That would certainly have put off other clubs from trying to sign him on a free as he entered the final year of his contract.

“I was in bits, absolutely gutted,” Anderton claims. He thought it might have been Sugar who leaked it and rang him up to challenge him about it.

“My then-girlfriend was there and after the conversation was like, ‘Is that how you talk to your boss?’

“Because I said to him, ‘How dare you? I could have gone off to United, but I’ve been loyal to you. This is f*cking bullsh*t, I’ve gone out and played with a torn groin (a reference to a game against Sheffield Wednesday in 1997 Anderton was asked to sit on the bench as he recovered from injury to give the crowd a lift. He ended up having to come on for the final few minutes).

“I was in tears after this injury and the next day I have to read about it. It’s f*cking awful.”

But Anderton was guessing and Sugar has always denied the story came from him.

Anderton and Sugar, who generally got on well, had also disagreed on how Anderton best recover from a groin injury before the 1998 World Cup. On England manager Glenn Hoddle’s advice, Anderton had started to see the faith healer Eileen Drewery.

“Hoddle was complaining to me that Darren Anderton was one of his star players, and we had to keep him in cotton wool so that he was available for England and that Gerry Francis had the audacity of making him run in a forest at pre-season training. Are you having a laugh or what? And then Anderton got injured, he sent him, he recommended that Darren Anderton go and see this woman called Eileen Drewery.

“I didn’t know who she was. I thought she was some kind of physiotherapy expert. Until my chief physio said she’s not a physiotherapist, she’s a faith healer. ‘You’ve got to be bloody kidding me’, I said. I’m paying Anderton £20,000 a week and this woman rubs her hands over him and is making him think of England.”

Sugar was becoming increasingly exasperated with his playing staff. “I remember some of the players saying to me, ‘Why don’t you buy some more players? We need some more players’.” Sugar recalls.

“I think Teddy Sheringham said that to me. I said, ‘Really? OK, perhaps you could tell me which players? Who’s the bad player? Would you like to point the finger at who are the bad players and which ones should be replaced? Should I replace you? And then he shut up because he realised he was talking a load of crap.”

Sugar ultimately sold Sheringham to Manchester United in 1997 after a disagreement over a new contract.

“Sheringham was young. He’s far more mature now and in hindsight, he would have spoken to me with far more courtesy and respect but he used to speak to me as if I was some kind of toe rag, and of course I wouldn’t stand for that. In the end, I said, ‘You’re going to clear off because if you don’t want it (the new contract), sod off. Go somewhere else’. And that was it.”

There were others too who acted up in front of Sugar: “The goalkeeper (Ian) Walker sometimes acted like a clown.”

Sol Campbell’s refusal to sign a new contract and ultimately leave for bitter rivals Arsenal soon after Sugar had sold up is a source of regret. As he recently explained to The Athletic, Sugar angrily confronted the defender after he claimed no one at the club had spoken to him about a new deal. Sugar also revealed that if he had had the authority, he would have chucked Campbell in the reserves.

Perhaps it was a case of familiarity breeding contempt. Sugar was a frequent visitor to the dressing room before and after games (even occasionally at half-time according to a few of the Spurs players), which was appreciated at some times, less so at others. Some felt it undermined the manager, while Francis himself remembers that: “He came in once when I was giving a post-match team talk and I had to tell him I wasn’t finished.”

Goalkeeper Espen Baardsen, who later quit football for a career in the city, remembers receiving stock tips in the dressing room from Sugar. On occasions like these, Sugar’s gregariousness was appreciated, and former Spurs colleagues remember two sides to him: the ferocious Apprentice-style boss, and a softer family man. “When I met him at his house with his family, he was a different personality,” Francis says. “He used to take my parents on his plane to games. They loved it. He was my best chairman.”

And you could joke with him, kind of. Francis remembers a tense Sugar ordering him to finalise a professional contract for a young Ledley King after a run of losing their best prospects to other clubs. The deal went through without a hitch, but Francis told Sugar that King had instead signed for Manchester United. “He went absolutely mad,” Francis recalls. “I just moved the phone away from me as he ranted. ‘You f*cking this and that’.” Eventually, Sugar saw the funny side of it.

Then there were events like the Christmas party thrown on Lord Sugar’s boat. “We had quite a few drinks on there,” Anderton remembers. “I think he ended up having to kick us off.”

The playing side of things continued to be problematic, however, and by the start of the 1997-98 season, Spurs had failed to kick on under Francis. After the promising 1994-95 campaign, they finished eighth and 10th, and weren’t much closer to escaping the mid-table mediocrity that defined the Sugar years.

A big problem was recruitment, which after the success of that 1994 summer became defined by near misses and a lack of clarity. Spurs decided against pursuing Dennis Bergkamp, who would have been open to a move because they felt, perhaps justifiably, that they already had a similar player in Sheringham. The following year Sugar coined the phrase “Carlos Kickaballs” to describe the foreign mercenaries he feared coming to England to ride the Premier League gravy train.

During this period, Spurs were also pipped to the signature of Emmanuel Petit, who underwent a medical at Tottenham and then used a cab paid for by Sugar to head to Arsenal vice-chairman David Dein’s house and sign for them instead. He and Bergkamp won the double the following season.

Tottenham could consider themselves unlucky on that occasion having watched Petit all season only to be scuppered by his close relationship with his former manager at Monaco Arsene Wenger.

On other occasions, it was a slowness to act that cost them. Take centre-back Ramon Vega, whom Spurs identified as a target and could have signed for less than £1 million in the summer of 1996. Instead, they waited and by the time Euro ’96 started, Vega, on the back of impressive performances for Switzerland, was firmly in the shop window.

Reflecting on it now, Vega recalls meeting Francis at the upmarket Langan’s restaurant in Mayfair during Euro ’96, but having stood out against England in the tournament’s opening game, many other clubs were now circling. In the end, Serie A side Cagliari moved quickest.

Spurs still wanted the defender and approached Cagliari about a transfer that summer, but didn’t want to meet the £1.8 million asking price. By the following January, Sugar had taken hold of the situation and Spurs finally got their man — for £3.75 million, almost four times what they could have originally paid.

Once Spurs really put their energies into the deal it was an easy sell, recalls Vega, who received a call from Sugar while the chairman was in Florida for Christmas. “This very direct way of talking surprised me — it was not the usual fluffy English way of talking,” he says. “It made me immediately decide, ‘yes’.”

Ronny Rosenthal, who was signed by Spurs during the Sugar era in 1994 and has since gone into the world of talent-spotting, believes the club were hamstrung by their recruitment. “Tottenham fell a bit short then because some other clubs at that time maybe had better scouting,” he says. “Spurs started looking at foreign players around 1994. For me, it (the lack of trophies) was to do with scouting, not with how the club was run.”

The most salient example of this was the disastrous appointment of Christian Gross as manager in 1997. The relatively unknown Swiss was appointed on the recommendation of Klinsmann’s agent Andy Gross (no relation of Christian), whom Sugar trusted. Sugar even had to a steer from Arsenal’s Dein, who informed him that Sir Bobby Robson might be available.

“Christian Gross, it was a mistake,” Sugar says now. “I was listening to bloody agents there.”

“Alan thought, ‘Here’s a guy (Andy Gross) we can trust’,” says Littner. “And so when he suggested Christian Gross, I think Alan was all too ready to say, ‘OK, fine, you’ve found us a very good player before, so maybe this is the right manager’.”

Gross failed to win the respect of the players, and in a sign of the building chaos at the club, his first signing was Klinsmann — against the chairman’s wishes. “I didn’t want to bring him back but Christian Gross and Andy Gross, who was Klinsmann’s agent, had a plan,” says Sugar. “Before I knew it, they said he’s coming back. I said, ‘I think it’s a bit of a slap in the face’.”

In the end, though, Klinsmann’s goals saved Spurs from relegation but the club finished 14th, just four points above the drop zone — a sign of how little the club was progressing.

Gross’ authority was shot, and at the start of the following season, Baardsen even recalls an incident when he was left wondering if the manager had total control of team selection. Baardsen told The Athletic in January that: “I was in the training ground on maybe the Wednesday and we were going to play Everton away on the Saturday. On my way in, Sugar walks in and goes, ‘All right son. You want to be in the team on Saturday?’ I was like, ‘Sure.’ He was like, ‘OK, you’re in’.

“I didn’t think anything of it. I thought he was joking or testing me. I certainly didn’t think he picked the team but I played the next match ahead of Ian Walker.” It could have been a throwaway line from Sugar or maybe Gross had already told him Baardsen was in. Certainly Sugar has always denied being involved in team selection.

The Everton game Baardsen refers to, a 1-0 win, was Gross’ last in charge. He was sacked just three games into the new season in September 1998, having lasted less than 10 months in the job.

The catastrophic Gross era was catnip for a press that was increasingly hostile to Sugar and his Spurs project. “The media really had a go at us,” says Littner. “Maybe just because of Alan’s profile, maybe it’s because they all loved Venables. And to a certain extent, if somebody attacked Alan, he felt obliged to defend himself.”

The media criticism was nothing compared to a fanbase who were becoming increasingly disillusioned. “It was a period of stagnation,” says Tottenham fan and blogger Alan Fisher, who since 1970 has been to around 95 per cent of the club’s home games and, with Martin Cloake, wrote the book A People’s History of Tottenham Hotspur.

“It felt like there was no direction. It was when another of the Spurs cliches came about: transitional seasons. This was a decade of transitional seasons. Gross was a disaster.”

Such was the frustration among the fanbase that a small section of supporters even became violent. “When the fans were unhappy they became quite brutal,” says Littner. “We’d very often find our cars vandalised. I can understand it. The fans — and I am a fan — just want to win. They just want to enjoy watching their team. And so, when you fail to do that even though you’re not responsible for that, the obvious targets are the directors.”

After sacking Gross, a baying media and febrile fanbase awaited Sugar’s next move with bated breath. Who would he appoint as manager to appease Spurs’ increasingly agitated supporters?

The answer was not a safe choice or someone who might have provided a public relations boost. It was a man synonymous with Tottenham’s loathed rivals Arsenal, and seen by many as the antithesis of what Spurs stood for.

George Graham was, in trophy terms, Sugar’s most successful manager. He won the only silverware of the period — the 1999 League Cup — and the side reached two FA Cup semi-finals.

But Premier League finishes of 11th and 10th underlined the lack of consistency, and it was the circus around the appointment and subsequent sideshows that eventually convinced Sugar to sell.

More than 20 years on, Sugar regrets the appointment, believing then-Leicester City manager Martin O’Neill would have been a better option. David Pleat had been brought in as director of football since the Gross appointment, and Sugar feels he could have been stronger in making the case for O’Neill. Instead, Sugar pressed on with appointing Graham despite the likes of Pleat and deputy chairman Tony Berry warning him of the risks of appointing an Arsenal legend.

Sugar claims that at the time he made the decision because he was told that Graham was in the same league as Wenger and Ferguson, the two dominant managers at the time. In reality, Graham’s last league title had come in 1991, and having been sacked by Arsenal because of an alleged bribe scandal, his most recent job at Leeds had been a solid if unspectacular success. They’d finished fifth the previous season. Was this enough to justify appointing an Arsenal legend who was so associated with the kind of dour football that was deemed anathema to Tottenham?

As with the Gross appointment, did bringing in Graham reflect a lack of footballing expertise at the club? Sugar points to the likes of Pleat and Tottenham legend Martin Chivers in response, while World Cup-winner Martin Peters was one of those at the club saying Graham had the best credentials for the job. But a sense remains that Sugar, by his own admission no football expert, needed more support.

No one doubted Sugar’s financial acumen, but the uniqueness of the football industry meant that what worked for Sugar’s other companies would not necessarily work for Spurs. He has since admitted, for instance, that he saw appointing Graham as no different to hiring someone from IBM to his computer business.

Vega — who after retiring from football moved into hedge funds, private equity and asset management, and now operates as a sports business consultant — has an interesting perspective on this.

“Tottenham was extremely well run under Sugar. But no doubt he needed to learn what the football industry is all about. Like most owners, they go into it thinking it’s like whatever business they made their money from, but it’s not. Football is completely different, which is something investors and owners underestimate quite a lot.

“Sugar learned that football is not as clear and transparent as the business world. You have to have business knowledge if you’re running a football club, yes, but you also need to know the politics of it, understand how things work behind the scenes.”

Francis adds: “He was learning on the job. The strange thing with football is that most football owners are people who have earned their money and built their reputation in completely different industries. And they don’t really know about the industry they’re going into.”

Either way, appointing Graham went down extremely badly with the Tottenham fans, who would not sing his name, even when results were good. “Man In a Raincoat’s Blue and White Army”, was his terrace chant.

“Appointing Graham didn’t endear Sugar to supporters,” says Fisher. “Tone-deaf is a polite way of putting it. George Graham is the anti-Spurs. Whatever Spurs stand for, he’s the opposite — including winning things, you could say!

“But as well as the Arsenal stuff, it was clear Graham was past his best and on a downwards slope. So it felt like a message that Spurs were second best and aiming to be also-rans. That also didn’t sit well with the fans, especially in the context of feeling very distant from the club. Sugar often made us feel like we were kind of getting in the way of whatever he was trying to do.”

Drawing parallels with Jose Mourinho, another manager about whom fans were dubious when he was appointed, supporters would have been more willing to accept Graham if there were tangible signs of progress. Instead, following the League Cup win five months after his appointment, Spurs never looked like being much more than a mid-table side.

And for Sugar, Graham’s perceived arrogance and untouchability with the media brought back painful memories of the Venables days. “God’s other gift to football,” Sugar sardonically describes Graham.

He was enraged by Graham’s frequent pleas for more signings, often delivered via the media, and their relationship ultimately completely broke down.

It still irks Sugar that he allowed himself to be “hung out to dry” by Graham, and perhaps surprisingly one of his regrets from his time at Tottenham was that he wasn’t more belligerent: “That, if anything, was the biggest mistake I ever made — being allowed to be hung out to dry by some of the managers. Like George, classic George Graham.

“My only regret is that I never hung the manager out to dry, particularly George Graham.”

Two of Sugar’s biggest bugbears with Graham were his “very frustrating” perceived cosiness with the press, and his frequent complaints that he wasn’t being backed in the transfer market.

“George Graham every three months would say, ‘We just need another three players, we just need another three players, just another three’,” Sugar says. “He bought 15 players under my watch and didn’t do that well.”

The two issues combined when after an embarrassing League Cup defeat by second-tier Fulham in December 1999, a story appeared in the Daily Mail with the headline: “Why miserly Sugar must come out of his counting house and give George the money”.

“That’s when I really lost it,” Sugar says. “I went into the training ground the next day and I gave Graham hell, absolute hell.

“I told him I’m going to court with this guy (journalist Jeff) Powell and you are going to get on the witness stand and you are going to give evidence. He sh*t himself quite frankly and right up to the 11th hour, he still thought that he was going to be called as a witness.”

Sugar won the libel case in February 2001 and was awarded £100,000 in damages, which he donated to Great Ormond Street Hospital. At the start of the trial, Sugar broke down in tears — the culmination of a bruising decade as a football chairman. “Absolute frustration brought me to tears,” he has said since. “Total frustration. When you’ve got in the court room sitting along the back there, you’ve got vultures. Vultures with their pens out all from the backpages of the newspaper.”

It was a similar sense of frustration that had led Sugar two months earlier, in December 2000, to agree a £21.9 million deal that saw ENIC become the majority shareholder. Relief was then the overwhelming emotion for Sugar.

Another dismal League Cup defeat to a second-tier side, this time a 3-1 home loss to Birmingham City, at the end of October convinced him to go. The supporters were in a state of open rebellion. “There was a real groundswell of opposition to Sugar,” says Fisher. “He’d been there nearly a decade and it felt like we’d achieved nothing.”

Did the fan criticism sting Sugar? “I’m quite thick-skinned and happy to go through tough things if it’s fair. In business nothing is smooth and you have to be thick-skinned but in football, nothing was fair towards the chairman. it was the chairman’s fault for everything and that makes you very cynical.

“A lot of the supporters if you talk to them in the street they say thank you Alan, thank you for rescuing the club, because a lot of them are very sensible. A lot of them really hold the club in their heart but then you’ve got another section of the supporters who are academically taxed if you know what I mean and I think a bit thick. If someone scored a goal against us, it was my fault, screaming and shouting (at me).”

Supporters’ frustration, Fisher says, stemmed from the fact that “it seemed that Lord Sugar was more than happy to accept mid-table mediocrity and the club’s finances being on a relatively even keel”. Again, perhaps it is the disconnect between the feelings of a supporter and the economic considerations of a businessman.

In any case, Sugar’s relief was palpable when he completed the sale to ENIC in December 2000. His son-in-law later joked when he asked to take his daughter’s hand in marriage that he hadn’t seen Sugar so happy since he’d sold Tottenham.

The takeover itself was set in motion when ENIC, headed by Levy, approached Sugar a few months before he decided to sell. Sugar knew the Levy family, who had also lived in Chigwell, and after the “last straw” of the Birmingham game, decided that he had to step down.

“Daniel, who I’d known slightly, expressed a wish to buy Spurs,” remembers Littner. “I think Alan, at that stage… I’m not saying he’d fallen out of love, but he’d had enough of the abuse.

“So Daniel said to me, ‘Can you see if there’s an opportunity for ENIC to buy the club? I went back to Alan, they then carried on negotiating and ultimately he decided that it was time to exit. There was no friction. The two parties came together and decided that the price was right, the time was right, and the deal was done.”

When Sugar met Levy he thought, “I’ve got out of jail.” He said to his ultimate successor, “Thank god for that, Daniel. I don’t need this aggravation and thank you. I’m still going to come to the club, I’m still in the boardroom.”

“I went to every game afterwards”, Sugar continues. “I was very supportive of the club, no sour grapes.”

If he held more than 29.9 per cent of the shares, Levy would have been forced to make an offer for the whole club. So instead, he bought enough shares from Sugar to get to just under that figure, paying the former chairman £21.9 million and leaving him with a 13 per cent shareholding in Spurs. Sugar then sold those remaining shares to ENIC in 2007 for £25 million.

Sugar and Littner have both been extremely impressed by the job Levy has done at Spurs.

“Daniel’s one hell of a shrewd bloke, don’t you underestimate him,” Sugar says. “He might come across a bit quiet, a bit lacklustre in personality from time to time but don’t ever underestimate him. He is a tough cookie.”

Sugar could have held on for longer to try and extract more from the sale but it was clear the time had come. “He’d done his best,” says Littner. “He’d had some great success. But ultimately, the fans didn’t appreciate him, the press didn’t appreciate him, and he saw other opportunities elsewhere.”

For the first six months after the sale, Levy was sometimes on the phone to Sugar and Littner asking for their advice. But over time he settled and has since taken Spurs to another level.

Reflecting on his time at Spurs, Sugar shoots back with, “Nothing. Nothing,” when asked what he feels proud about from his time as chairman.

He goes on to say that putting the club on a sound financial footing and redeveloping the stadium were notable achievements, but adds that “nothing much went well on the pitch”.

He stands by previously calling his time at Spurs “a complete waste of my time” and expands by saying: “Because I’m a clever man and if I’d deployed my brilliance, if you like, for 10 years into something else, I would have made a lot more money than I did in football.”

The close to £50 million Sugar recouped for his shares was, he says, “unprecedented” but running the club took a big toll mentally: “You have to be very, very, very careful with every single word you say, or they’ll sell the story to The Sun or whatever.

“And that made me not a nice person. It was quite a relief when I left there because I didn’t have to have this barrier around.”

Sugar still feels fondly towards Tottenham, though according to some of his one-time adversaries around the club, a degree of bitterness remains. One source who clashed with Sugar over a player’s contract says the former chairman will absolutely look the other way should they ever run into each other at a match.

Others, though, enjoy a more cordial relationship with the owner and are sanguine about his time at Spurs. Despite their run-ins, Anderton says he and Sugar get on fine now and had a nice chat when they ran into each other on Bond Street in central London last year. Anderton also says that when Levy came in, “I realised the dealings I’d had with Sugar were probably better than I thought because I always knew where I stood with him”.

Francis, meanwhile, is still in touch with Sugar and speaks regularly with his son Danny. He, Anderton and the likes of Vega and Rosenthal think Sugar did a good job at stabilising the club and putting Spurs on a sound financial footing.

For the Spurs fans though, the league finishes of 15th, eighth, 15th, seventh, eighth, 10th, 14th, 11th and 10th and a sense of disconnect still rankle.

“It was a period where fans felt more and more distant from the club,” says Fisher. “There was no consultation with the fans. It felt like Sugar was treating us as mug punters — that we would always turn up. Which was true. So who’s the mug?

“Towards the end when fans complained, the feeling was he’d turn around and effectively say: What do you expect? We don’t have loads of money to compete with the big boys. We don’t have a massive ground, I inherited loads of debt.

“Well, OK, we understand that but he didn’t seem to understand that there were ways of investing in the team so that we could get to that position.”

While for those like Perryman there remains a feeling that the period was a departure from Spurs’ traditions.

How do those in charge look back on it? “It was a cultural change because I’m very much an autocrat,” says Sugar. “I was told at a very early stage that I don’t get involved in the players or anything like that. So you shut up and you let the manager do all the talking.

“An autocrat is a person who’s always in control of everything that they do,” Sugar continues. “To be completely out of control was a bit alien. Not only that, but to then be blamed for it (bad results) when it had nothing at all to do with me… it was difficult.”

“If I reflect on my time at Spurs, I think that I made mistakes,” says Littner. “I didn’t appreciate that the heart and soul of the club is the football. I was too focused on putting things right, just like you’d do in an ordinary company. Getting it organised, managing properly, having things under control, when really it didn’t need that level of control. If I had my time again, I’d try to befriend the managers.”

Littner points to the close relationship between Levy and Mourinho now and says the club appears to be, “Much more ‘we are one’. And I think that’s what we didn’t achieve.”

Like Sugar though, Littner believes the 1990s was a stabilising time for Tottenham and laid the foundations for the Spurs we see today.

And Scholar, before Sugar, looks back with pride at his own era of stewardship of the club. “I am proud to have been one of the five founding members that were responsible for the creation of the Premier League,” he says, “that Spurs and so many other clubs have benefitted from since its creation.”

One thing that is clear is that it was one of the most tumultuous periods in the club’s history. Twenty years on, it continues to throw up surprises.

So what did Sugar learn from his decade in one of the most pressurised roles in the sport? “The biggest learning,” he says,“was discovering the horrible world of football and the hopeless task of trying to create success in that industry.”