Daniel Levy’s nine most controversial moments as Tottenham chairman

After 24 eventful years as Tottenham chairman, Daniel Levy’s reign is over, ending as swiftly and abruptly as some of the managers he dismissed.

As the Premier League’s longest-serving and highest-paid chairman, Levy’s departure sent shockwaves through English football. He retains a 29.88 per cent stake in the club, but is no longer calling the shots.

Levy’s legacy is partly defined by the magnificent shiny dome in north London, the impressive modernistic training ground, and the club’s top-10 position in world football’s revenue league.

However, he also faced criticism for some of his other decisions. Here are nine of the most controversial.

Tottenham Hotspur manager Thomas Frank (left) and chairman of Tottenham Hotspur Daniel Levy arrives to the stadium ahead of the pre-season friendly match at Kenilworth Road, Luton. Picture date: Saturday July 26, 2025. PA Photo. Photo credit should read: Nigel French/PA Wire. RESTRICTIONS: Use subject to restrictions. Editorial use only, no commercial use without prior consent from rights holder.
Levy with his final managerial appointment, Thomas Frank (Photo: PA)

Jol’s departure at half time

Martin Jol was the first successful managerial hire of the Enic era, and one that was almost an accident. He initially joined as an assistant to Jacques Santini.

The Dutchman quickly gained popularity among fans for his amiable outlook and entertaining, end-to-end football.

It came as a shock then, when he paid the price for a poor start to the 2007-08 season. News of Jol’s demise filtered through at half time while he was overseeing a Uefa Cup tie against Getafe.

Stratford move interest

Spurs needed to move on from White Hart Lane to increase their revenue potential and initially, they identified Stratford as a potential new home.

The club planned to take over the Olympic Stadium, demolish it and build a football stadium in its place, while also refurbishing Crystal Palace as a bespoke athletics stadium.

Naturally, it caused uproar among fans given Stratford’s east end location. A bullet dodged, given how unpopular the venue is with West Ham fans now.

No signings for 18 months

Mauricio Pochettino inherited a mess but transformed Spurs into Premier League and European contenders, despite limited backing in the transfer market.

Spurs famously went the whole 2018 summer transfer window without signing a single player.

Improbably, they reached the Champions League final that season, but the squad had become stale and the hugely popular Pochettino left soon after.

Replacing Pochettino with Mourinho

LONDON, ENGLAND - FEBRUARY 26: Tottenham fans hold up a banner protesting against their owners ENIC and chairman Daniel Levy prior to the Premier League match between Tottenham Hotspur FC and Manchester City FC at Tottenham Hotspur Stadium on February 26, 2025 in London, England. (Photo by Visionhaus/Getty Images)
Spurs fans have protested against Levy and Enic in recent years (Photo: Getty)

Although he didn’t win a trophy, Pochettino was the longest-serving manager of the Levy era.

Just five months after masterminding Spurs’ run to the Champions League final, the Argentine was ruthlessly sacked after a poor start to the 2019-20 season.

The following day, he was replaced by Jose Mourinho. It was a bold choice, given his abrasive nature and connections with fierce rivals Chelsea.

Furloughing club staff during Covid

In 2020, the government subsidised workers’ wages through its furlough scheme as businesses were locked down around the country.

Big football clubs worth billions of pounds attempted to use it for non-playing staff, drawing ire from the Department for Culture, Media and Sport, which said it exposed the “moral vacuum” at the heart of English football.

Tottenham reversed their decision, but only after vociferous criticism.

Sacking Mourinho before a Carabao Cup final

The logic behind hiring Mourinho was that his trophy-winning expertise would help a talented young squad, spearheaded by Harry Kane and Dele Alli, finally win some silverware.

Strangely, given that rationale, Mourinho was dismissed six days before a Carabao Cup final, with 29-year-old Ryan Mason put in interim charge.

Spurs lost 1-0 to Manchester City at Wembley.

Signing up for the Super League

In April 2021, 12 clubs, including England’s “Big Six”, plotted to break from their domestic divisions and join a European Super League.

The backlash was intense and instant, including at Spurs, where fans protested against the plans and the ownership outside the stadium.

“The actions of the current board have shamed and humiliated the club,” said the Tottenham Hotspur Supporters’ Trust.

Spurs withdrew from the Super League, with Levy apologising for “the anxiety and upset caused by the ESL proposal,” in a statement.

Sticking by Paratici

Fabio Paratici was one of Levy’s more successful sporting directors, but resigned in disgrace in April 2023 after being served a 30-month ban from football activity for being implicated in a financial scandal with his former club, Juventus.

Spurs insisted that due process was followed, but sticking with Paratici months after numerous board members had left Juventus wasn’t the best look.

Had it not been for his excellent track record in the transfer market – Cristian Romero, Dejan Kulusevski, Rodrigo Bentancur – Paratici surely would have gone far earlier.

Sacking Postecoglou after Europa League win

The crowning moment of Levy’s tenure at Spurs came mere months before his exit: the Europa League triumph in Bilbao.

It was only the second trophy Spurs have won this century (after the 2008 League Cup) and was overseen by Ange Postecoglou.

Thousands of Spurs fans gathered outside the stadium and along Seven Sisters High Road to celebrate the triumph, and roared in approval as Postecoglou said: “In] All the best TV series, season three is always better than season two!”

Alas, Postecoglou was cancelled after the second, ruthlessly, if justifiably sacked after Spurs’ shocking 17th-placed finish in the Premier League.



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