On arriving on Daniel Levy’s front doorstep to discuss the possible purchase of a big-name Tottenham player, the chief executive of one Premier League club was presented with an obstacle equally as formidable and determined as the Spurs chairman.
‘It was a little yapping dog,’ laughs the well-known CEO. ‘You know the type. Jumping at you all the time. Daniel soon intervened. “Get down Lilywhite,” he said.
‘And I had to laugh because that was Daniel through and through. A dog called Lilywhite. Tottenham. Always Tottenham.’
A suitable end to that tale – and one that fits with the popular characterisation of Levy as an unbendable negotiator – is that a deal for the player was not done that day.
‘To be fair, Daniel did sell him,’ adds our source. ‘The player actually chose another club. But as a negotiator, I would say the popular representation of Daniel is entirely fair.
‘You would always ask yourself: “Am I ready for this battle. Am I up for it?” Back in the day it was Daniel and Marina (Granovskaia, former Chelsea director from 2014-22 under Roman Abramovich) who were in that bracket.
‘But, yes, Daniel would get the gold medal. He knew all the tricks. In fact, he invented most of them. Over all these years he has been an incredible asset for Tottenham.’
Across the Spurs fanbase, opinions on their outgoing chairman are split. Some recognise the transition on his watch from also-ran to modern economic football powerhouse. Others accuse him of spending too conservatively on the actual football team. Two trophies in a quarter of a decade.
Across the Premier League and in the minds of those who has worked for and against him, there is more uniformity. Quiet, studious, obsessive and reserved almost to the point of shyness. But a scrapper all the same.
‘He is so hard to read,’ a current Premier League chief executive tells Daily Mail Sport. ‘You sit at Premier League club meetings and the same old people do the talking. You tend to switch off. It’s boring.
‘But Daniel only speaks when he has something important to say. And when he speaks everyone listens. That says everything. Do I know him? No. It’s almost impossible to know him. I think he likes that.’
Levy’s obsession with the bottom line is not in doubt. Spurs are now an enormously profitable football club that some insiders believe may soon break previous Premier League revenue records. Has he occasionally taken that too far? Some do think so.
Another former Premier League club board member recalls: ‘He was an ice man. I wouldn’t want to play poker with him. Very robotic.
‘During Zoom meetings about Project Restart in Covid times he was the one driving moves to get supporters back in the stadiums and the feeling from many of us was that he wanted to get the corporate punters back first.
‘He never said it straight out but he gave that impression. The reasons were obvious. More money.’
Meanwhile a well-known representative from one of the so-called ‘Big Six’ is similarly categoric about Levy’s contribution to the conversations around the failed European Super League proposals of spring 2021.
‘I have been around a while and I couldn’t actually believe what Daniel was like over that,’ tells our source. ‘I can only describe it as an obsessive doggedness. He just would not bend and his obsession with getting what we wanted down to the very last detail actually overrode the wider picture.
‘He doesn’t do k***-waving like some blokes. But equally he isn’t naturally affable. It feels like a forced politeness.
‘Daniel isn’t rude or arrogant. Not in any way. But the boardroom is not his happy place. I always felt he couldn’t wait for the match to start so that he could get out of there.’
As it happens, the boardroom at the new and shiny Tottenham Hotspur Stadium has been the fiefdom of Levy’s wife - and former PA - Tracy. For such a shrewd businessman, Levy also had a penchant for keeping things close to home.
Tracy’s brother Alan has worked at the club as matchday security and has been seen holding up the numbers for Spurs substitutes. Tracy, meanwhile, has been known to station herself at the door to the inner sanctum.
‘She can be just as formidable,’ reveals an executive from a rival club.
‘Before one game she wouldn’t let me in to the boardroom as I was wearing what she described as the wrong sort of shoes. I actually had to go and borrow another pair to get in.
‘And of course when I sat down in the directors’ box there was a whole row of Tottenham people wearing shoes exactly like the ones I had turned up in.’
If games were afoot that day, they are not typical of Levy’s 25 years at Tottenham. Most of the Premier League rivals contacted by Daily Mail Sport speak warmly of him and certainly with respect.
For example, when Ed Woodward left Manchester United in 2021, it was Levy who organised a farewell dinner for him at a London wine bar.
‘It wasn’t opulent, just really nice,’ says a source who was there. ‘Daniel wanted to do something kind for someone he liked and respected. It was that simple. And he didn’t tell anyone. Classic Daniel. Not showy.’
Certainly the chief executive greeted so enthusiastically that day by Levy’s dog recognises the impact the 63-year-old has had in North London and across the Premier League.
‘What he has done for Tottenham is unbelievable,’ he says. ‘The stadium is fantastic and the training ground is probably among the top three in the world. His vision around the women’s team and establishing the club in the heart of the community has been fabulous.’
Some Premier League clubs – burned in the past – have grown wary of doing player business with Levy’s Tottenham. At Manchester United, for example, long-protracted sagas required to extract Michael Carrick in 2006 and Dimitar Berbatov in 2008 left scars that didn’t heal.
Former United manager Sir Alex Ferguson described the Berbatov deal – concluded at midnight on the last day of the summer window – as ‘more painful than my hip replacement’.
And when Harry Kane made it clear privately that he would like to move to Old Trafford in summer 2023, club executives just couldn’t bring themselves to get involved in a process they feared would last all summer, then ultimately lead to Levy saying no when it was too late to recruit an alternative.
‘Yes, he is a very difficult negotiator,’ explains one of chief executive. ‘It was always a hard fight but a fair fight. He wouldn’t lie. There would be no tricks and he wouldn’t go back on his word. And more often than not it would be just you and him talking, one on one.
‘Ten or 15 years ago, it was a big three or four clubs in England. Now it’s a Big Six. Daniel fought hard to put his club in that group and he did it. As a person he is intelligent, reflective.
'He doesn’t rant or raise his voice and I would probably even describe him as marginally shy. He has no ego. He is a thinker. And he gets things done.’
Levy’s relationship with one of his more successful managers, Mauricio Pochettino, was warm. They even went on holiday together. But that’s the outlier.
Previous members of Tottenham’s backroom staff provide a less generous take. ‘He is just cold,’ says one. ‘You initiate conversation and just get nothing back.’
To some players, agents and coaches, Levy seemed unnecessarily parsimonious regarding contracts and bonuses and at one stage this hawkish obsession with money even extended to stressing about the amount of water players were drinking during training.
‘He would moan about the amount of wastage when players would take a single swig from a bottle before throwing it away,’ an ex-Spurs staffer explains. ‘It was a huge bugbear of his. He’d be on at us all the time to do something about it.’
Tottenham’s failure to qualify for the Champions League after players were famously laid low by food poisoning before the final game of the season in 2005-06 at West Ham infuriated Levy so much he considered calling the police. Again the financial loss – as much as the sporting disappointment – was said to be the driver.
Inside Tottenham Levy would discuss transfer targets in code. A1, A2 etc. It’s a way of ensuring even his own staff don’t know the identities. His preferred form of communication, meanwhile, has always been WhatsApp.
‘If you don’t respond within 10 minutes then he chases it,’ says a former Tottenham executive. ‘Daniel basically doesn’t sleep.’
Over the years, he has left an impression on managers, players and rivals alike. Agents have their memories too. One prominent representative still tells a tale of arriving suited and booted for a meeting with the Spurs chairman only to find him dressed in a hoody and jogging bottoms. The only tipple on the table was water.
Another big English club, meanwhile, bought one of Tottenham’s star names from them only to realise they were due to play each other a few days later. When they arrived at White Hart Lane, Levy presented their coaching staff with a bin bag with the player’s boots in. 'There,' he said. 'He’s your problem now.'
That, of course, would suggest Levy takes things personally and occasionally he did.
The rivalry with Arsenal was certainly real. Any red flowers that poked their noses through at the training ground would be gone within hours, while he vowed privately not to deal either of the two Manchester clubs again after City took Kyle Walker from him for £50m in 2017. Levy considered the deal undervalued.
Years later when Daily Mail Sport ran a report suggesting United may bid £150m for Kane, Levy told an associate: ‘I certainly won’t be selling him to them!’
Indeed, whatever the Tottenham fanbase say and however football judges him, Levy undoubtedly takes his leave with his club well-positioned to make the next steps.
Maybe it’s time for his Premier League rivals to throw a party for him. ‘It’s a thought,’ muses one of them. ‘The problem is that he probably wouldn’t come.'
