What Tottenham chairman Daniel Levy is really like

Sitting in his office at Tottenham’s training ground a few weeks ago, Daniel Levy was already starting to think he’d had enough of Antonio Conte. Enough of the noise. Enough of the average football. Enough of the disrespect.

A lame home Champions League exit to AC Milan only deepened his irritation. When his manager tore in to his players and the culture of the club after a draw at Southampton, Levy knew the time had come. Manager number eleven of Levy’s two decades as chairman of Tottenham was on his way out.

The search for a replacement will now take place without Levy’s football director Fabio Paratici after the Italian was banned from football activity by FIFA. But that will not worry Levy as much as some people think. Levy, 61, has hired managers on his own before. Conte was his decision. Jose Mourinho, over the head of Paratici’s predecessor Steve Hitchen, was his decision and born of a long-standing fascination with the Portuguese coach. Before that, back in 2014, Levy chose Mauricio Pochettino when his technical director Franco Baldini had a preference for Frank de Boer.

‘Daniel will listen to people but equally, when the mood takes him, he will just follow his gut,’ one long standing associate told Sportsmail this week.

‘He is quite capable of listening to absolutely nobody.’

Levy has a liking for foreign managers. He admires their work ethic. The problem he may have now is attracting the next coach, wherever they may come from. His reputation for being hard to work for – whether it’s actually fair or not – increasingly goes before him.

For example, when Tottenham were looking to replace Mourinho in the summer of 2021, the names of Brendan Rodgers and Graham Potter were on Hitchen’s list. Both, however, had reservations.

‘They need convincing about Daniel,’ football sources claimed at the time.

Tottenham have much to offer a football manager. A first in class stadium, a magnificent training ground and some very good players. So why the toxicity? And can it really be one man’s fault?

Daniel Levy is not a man unaware of public opinion or indeed that of his managers.

His inbox at Tottenham used to be so full of complaints from supporters that he changed his email address. But that doesn’t mean he is deaf.

‘If an email reaches Daniel he reads it,’ revealed a source this week. ‘And he has people around him who tell him. He knows.’

In terms of his managers and his executives Whatsapp is a preferred means of communication. Levy will often sit and chat at the coach’s table in the canteen at Spurs’ training ground. Indeed it was there where he and Conte briefly discussed – and decided against – a move for Cristiano Ronaldo last year.

But it’s the constant beep of mobile phones that form the backdrop to Levy’s management.

‘Back in my day it was Blackberry messenger,’ explained one former executive. ‘If you don’t respond within ten minutes then he chases it. Daniel basically doesn’t sleep.’

Levy’s commitment to the club he joined at the age of 38 is not in doubt. It is described by many who know him as an obsession. Whether his years in north London have been a success is harder to answer. Off the field, they have been. Tottenham were worth £80m back in 2001 and now the club is valued at £2bn. On the field, they have won one trophy – the 2008 League Cup – and it’s this that infuriates Tottenham supporters.

Season tickets at Tottenham are the most expensive in the country while Levy is the highest paid chairman. His reputation as a hard-edged, emotionless negotiator has earned him a respect inside football. There is an admiration for the prudent manner in which Tottenham are run. But too many supporters simply see a man whose unwillingness to bend or speculate continues to get in the way of footballing progress and that sits uncomfortably next to the money they must pay simply to watch their team play.

‘Daniel has an inability to read the room,’ said another football source.

‘The fans’ view is that he pays himself well but isn’t giving them what they want in return. He also doesn’t communicate with them enough to explain his strategies and that silence drives them mad.

‘He does not want to be famous. He is a businessman. But in football a reluctance to communicate is seen as indifference and that’s dangerous.’

This week has seen this rather clunky PR at work. In the wake of Conte’s departure – announced at 10.20pm on Sunday – Spurs placed some rather empty words from Paratici on their website when what Tottenham supporters really wanted was reassurance from their chairman.

One theory is that Levy has failed to surround himself with people with personalities to make up for the shortfalls in his own.

‘Daniel would prefer it if the world was full of robots,’ added a source from football commerce .

‘He can be great one on one. Personable and open. But he struggles socially, especially in groups. He is happiest with his head in his phone or writing emails, getting things done.

‘What he has never done is appoint a polar opposite. The Spurs board are good people but too many are just like him. They do care but that doesn’t come across and it’s their own fault.’

This is a view echoed at other football clubs.

One Premier League executive told Sportsmail: ‘Certainly the boardroom on match day is not Daniel’s happy place. There is a forced politeness.’

Within football, Levy’s reputation for hardness is well known. Agents tell of turning up to discuss deals to be offered nothing more than a jug of water, others to be greeted by a man wearing a tracksuit. He once made an enquiry about another London club’s top player by placing it as the final line of an email purporting to be about something else.

Meanwhile, when Peter Crouch was hoping to continue his enjoyable time at Spurs in 2011, Levy told him there would not even be a squad number if he stuck around.

‘It was harsh and ruthless but he’s just decisive,’ Crouch recalled. ‘He won’t accept drift. If I owned a football club I would employ Daniel to run it.’

Levy’s positioning as defender of Tottenham’s best interests stretches to extremities. He has never forgiven himself for sanctioning the sale of Kyle Walker to Manchester City in 2017 and has vowed not to sell to a Manchester club again. This club policy represents the main obstacle to Manchester United’s interest in Harry Kane.

During the negotiations over Tottenham’s part in the doomed European Super League two years ago, meanwhile, executives from other clubs were struck by Levy’s demeanour.

‘I can only describe it as a staggeringly obsessive doggedness,’ revealed a source.

A year earlier, meanwhile, two League chief execs came off a Zoom call to discuss the return of fans to stadiums post-Covid with one remarking to the other that Levy would open his doors to corporate customers first.

‘We were joking but only just,’ laughed one of those execs this week.

At Tottenham, Levy has had a habit of discussing transfer targets in code. A1, A2 etc. It’s a way of ensuring even his own staff don’t know the identities. Some of his work has been extraordinary. He took only 90 minutes to get Rafael van der Vaart out of Real Madrid in the final moments of the 2010 summer window and got a world record £85m out of the same club for Gareth Bale three years later. When Bale returned on loan two and a half years ago, he did so with Levy having persuaded Real to continue paying most of his wages.

But this cleverness can also backfire. The failure to spend the Bale money well has left a scar while some agents say Tottenham have lost players on the back of Levy’s focus on fine detail and exact structure of transfers. What’s more, agents have been known to walk away from talks disenchanted enough to then leak the details.

Supporters argue Levy’s record in the market comprises too many misses and their memories are manically long and selective.

Spurs have actually spent quiet heavily in the four years since appearing in the 2019 Champions League final but the recruitment has been scratchy while many still talk about the summer of 2008 when Levy drove United chief executive David Gill to distraction over the sale of Dimitar Berbatov. Levy eventually squeezed £31m out of Gill right on deadline by using late interest from City as leverage. But Spurs fans cared only that it was too late to buy a replacement.

Four years later with Harry Redknapp’s Spurs poised for a title tilt in January 2012, the manager asked for Carlos Tevez and Gary Cahill and was delivered Ryan Nelsen and Louis Saha. A two-point deficit behind eventual champions City had grown to 20 by the season’s end.

Spurs have reached that Champions League final since then and registered six top four finishes. In the era of the superrich of Manchester, Chelsea and now Newcastle, this feels like Tottenham’s level. Levy’s public say otherwise.

Tottenham’s best recent years were spent under Mauricio Pochettino. Levy and his Argentinean coach built a young, physically impressive and tactically smart football team that could have won the Premier League and the Champions League but ultimately won nothing.

It is hard now not to wonder how much this affected Levy and how much it has influenced the way he has approached life at Tottenham ever since.

The Pochettino/Levy relationship was all-in. They spoke so much Levy’s wife Tracey described Pochettino as the third member of their marriage. As he looked to build a football club in Pochettino’s inclusive, holistic and future-proofing image, Levy even took mini-breaks with his manager, to his own chalet in the French mountains and to South America. He gave him a Bentley and expensive bottles of red wine, a shared passion.

‘People don’t realise how much it took for Daniel to do this,’ revealed a Spurs source.

‘He is so far out of his comfort zone with that bonding trip stuff it’s untrue.

‘But he did it for Mauricio. Other clubs were buzzing around him. Barcelona. Manchester United. Daniel knew he couldn’t keep him with money so he kept him with love. It was smart.’

In his book about the 2016-17 season, Pochettino wrote: ‘It is difficult for a chairman and manager to trust each other but Daniel and I are looking for mutual understanding. It’s part of a process to rediscover the club’s identity’.

If this was to be a new Spurs ID then it was impressive. Young players, a strong academy, attractive football. After one win against Chelsea, Levy confessed he couldn’t sleep due to the excitement. He broke a habit by occasionally appearing in the home dressing room. When Spurs beat Ajax to reach the Champions League final, Levy ran on to the field.

The only problem in the long-term was that when the Pochettino era ended – when he finally lost his energy and willingness to work within the financial parameters imposed on him by the construction of a new stadium – there was no succession plan.

Transitioning from Pochettino to Mourinho only a few months after a Champions League final that should have acted like a springboard was like moving to night from day. Levy sacked Mourinho days before the 2021 League Cup final.

The former Wolves manager Nuno Espirito Santo was a Paratici appointment and then came Conte. The identity that Pochettino and Levy had constructed was allowed to disappear like dust, replaced by what has looked like a short-term desperation simply to win something.

Last summer with Spurs back in the Champions League, Conte was given a lot of money to spend. That in itself was another departure and now that it has failed Levy is left with a wasteland on which he himself must now rebuild doubtless with the help of favoured agents such as Leon Angel, Pini Zahavi and the Dutchman Frank Sedoc.

Tottenham are fourth in the Premier League but there is disquiet among some who love the club. They say the support staff under Paritici is bloated. ‘Too many Italians with lanyards,’ was one pithy observation. Others think a disconnect with the academy has developed. Some close to Spurs think Levy may have asked his football director to leave this summer anyway.

Levy’s desperate will for the club to succeed remains. The father of four is not a machine. He has a human side. He organised a leaving dinner for Ed Woodward when the United executive vice-chairman quit Old Trafford. Once, on a trip to Moscow, he took the microphone at a karaoke and his rendition of Elton John’s Crocodile Rock is believed to live on in mobile phone footage. His wife Tracey will arrange dinners for coaches’ wives while her brother Alan works at the club as security, even holding the board up to signal Tottenham match day substitutes. On the day Tottenham left White Hart Lane in May 2017, Levy gave a speech of gratitude in the boardroom that reduced some present to tears.

Back in the days when Levy was new to football, he would not go alone to Premier League board meetings. That was due to shyness and a lack of understanding of the industry.

‘He was quiet as a mouse,’ a source said.

That is not the Levy of 2023. In English football, he has become a major player. When the FA cut the ribbon to the national teams’ new base at St George’s Park in 2012 Levy went along and left satisfied it was not superior to what he was building in north London.

He’s like that, Levy. Competitive. Single-minded. But football is not won and lost in bricks and mortar. Success comes from what you do on the grass. After two decades of trying, this is the part Levy and his beloved Tottenham are yet to get right.