At Tottenham, escaping the shadow of an Arsenal legacy proves challenging, especially when plans go astray and results falter. This becomes particularly evident when a sudden exodus of key figures leaves the club vulnerable and thrust into the limelight.

Vinai Venkatesham has found himself in a precarious position just six months after taking over the day-to-day operations at Spurs following the departure of chairman Daniel Levy. His assurances of prudence and steadiness have instead ushered in a period marked by chaos and instability.

The departure of Levy initiated a significant upheaval in the executive ranks, compounded by Fabio Paratici’s short-lived return as one of two sporting directors before his abrupt exit amidst a crisis. This was followed by the dismissal of head coach Thomas Frank as the team dangerously flirted with relegation.

Venkatesham’s tenure as Spurs’ chief executive spans ten months, a role he assumed less than a year after leaving a similar position at Arsenal. He succeeded Scott Munn, who was sidelined after failing to make a significant impact in his two years as chief football officer.

Following the dismissal of Ange Postecoglou, a new chapter began with a joint interview featuring Venkatesham and Levy in June, after Frank’s appointment. The two awkwardly bantered about their mutual appreciation for red wine and hard work, while discussing the selection of their new manager and vowing to build on their Europa League triumph.

Life has become uncomfortable for ex-Arsenal man Vinai Venkatesham in the space of six months since he assumed responsibility for day-to-day affairs at Spurs

He promised to build on the success of Tottenham winning the Europa League last May

Venkatesham is now the butt of jokes at the other end of Seven Sisters Road about an Arsenal agent sent undercover to sabotage the neighbours

Levy had voiced ambitions of winning the Premier League and the Champions League, but by September, his lengthy reign of nearly 25 years as chairman came to an end as he was ousted from the club.

Peter Charrington became non-executive chairman but Venkatesham quickly surfaced as the front man, running day-to-day affairs under the watch of Vivienne Lewis, daughter of the club’s billionaire former owner Joe, and her son-in-law Nick Beucher.

This raised a few eyebrows at Emirates Stadium, where Venkatesham was well liked and admired for his decency and diligence, but seen essentially as a corporate executive.

He joined Arsenal having worked previously on London 2012, and different roles led him to the post of commercial officer, then managing director when Ivan Gazidis left in 2018 and chief executive two years later before stepping down in 2024.

At Spurs, he was thrust into a triumvirate of power with two Danes, Frank and sporting director Johan Lange. Together they were three logical minds, advocates of stability and sustainable growth. One of their first moves in the post-Levy era was to reappoint Paratici as a second sporting director, once the ban for his part in the Plusvalenza financial scandal in Italian football during his time at Juventus had expired.

Paratici resigned as managing director of Spurs in April 2023 when the ban was confirmed, although was seldom far from the club, retained on a consultancy basis. His return seemed on one hand to be Venkatesham, Lange and Frank accepting there was a gap in their expertise, and they would probably need Paratici’s vast network of contacts and deal-making influence in the transfer market.

On the other hand, it seemed to be a recipe for disagreement. And so it proved. Quite quickly, in fact.

Paratici had pushed for Roberto De Zerbi as head coach when Frank got the job and was later suggesting Frank ought to be sacked, claiming the job was too big for him and that he could still get De Zerbi out of Marseille or Tudor, who had been out of work since his sacking by Juventus in October.

Fabio Paratici’s return seemed to be Venkatesham, Johan Lange and Thomas Frank accepting there was a gap in their expertise

Venkatesham was keen to hold his nerve and back Frank despite deteriorating form, insisting it was vital Spurs broke the culture of hiring and firing

Venkatesham and Lange were keen to hold their nerve and back Frank despite deteriorating form, insisting it was vital Spurs broke the culture of hiring and firing. Venkatesham had overseen Arsenal’s transformation by staying loyal to Mikel Arteta despite teething troubles at the start when he was unpopular among many fans.

Frank, like Arteta had at Arsenal, identified culture as the key to success and Venkatesham, like he had at Arsenal, set about re-engaging with the fans’ groups disenfranchised under the Levy regime, in the hope of repairing lost connections and creating a better atmosphere inside the stadium. But the Tottenham Hotspur Supporters’ Trust have expressed their irritation at the lack of clarity, following meetings with the club, over a direction of travel.  

Levy had always been dead set against statues of heroes around the stadium, but Venkatesham was open to the idea – Arsenal legends dot the surrounds of the Emirates after all, with Thierry Henry, Dennis Bergkamp and Tony Adams among those cast in bronze. 

A singing section was trialled at Spurs’ FA Cup tie against Aston Villa. Arsenal created an area at the Emirates for the ‘Ashburton Army’ to improve the atmosphere at the ground. 

Spurs in the past have been accused of having an unhealthy obsession with their neighbours. Postecoglou thought it indicated the ‘foundations’ of the club were ‘fragile’ when fans celebrated losing to Manchester City in May 2024 because it damaged Arsenal’s title hopes.

This was reinforced in the wake of the departure of Frank – pictured holding an Arsenal coffee cup before a recent Spurs match at Bournemouth – when it was suggested he had been undermined because he repeatedly made his admiration for the Gunners clear during his eight months at Spurs. So much so that it reportedly annoyed the Spurs players.

Of course, results trump everything, even the best intentions, and as a decent start faded and Frank’s team plunged down the league, Paratici grumbled about the way the club was being run post-Levy and leapt at a chance to leave when Fiorentina approached in December.

Spurs demanded that he stayed in post until the end of the January transfer window, although his mind seemed to be elsewhere. Fiorentina made five loan signings in January after all. 

Spurs, despite Frank’s claims that they had been busy making plans since September, spent £35million on Conor Gallagher only when Rodrigo Bentancur was injured in January

Frank, pictured holding an Arsenal-branded coffee cup before a game at Bournemouth, irritated some Tottenham fans with his positive comments about their rivals

Meanwhile, Spurs, despite Frank’s claims that they had been busy making plans since September, spent £35million on Conor Gallagher when Rodrigo Bentancur was injured and signed teenage left back Souza from Santos in Brazil.

The transfer window became another disappointment for Spurs fans. They wanted to see more activity to arrest the slide, especially as more injuries piled up. There were five serious injuries in five games in January. Claims that they were ever serious contenders for Antoine Semenyo or Marc Guehi hinted at a misguided recruitment policy when both those players ended up at Manchester City.

Spurs considered testing West Ham with a bid for Crysencio Summerville and the idea of Raheem Sterling as a free agent was discussed as the injuries took hold, but Frank said they decided not to interfere with summer recruitment plans.

Paratici started at Fiorentina on February 4, one week before Frank was sacked and yet his lingering influence was clear when Tudor was appointed interim head coach. The Croat and the Italian know each other well from Italian football and worked together at Juventus in 2020-21 when Tudor was assistant to Andrea Pirlo.

Spurs had drawn up contingency lists of interim managers at the start of this season when Paratici was part of the committee, so Lange and Venkatesham simply turned to the working list of options when they sacked Frank after losing at home to Newcastle.

Hardly a case of Venkatesham and Lange thinking on their feet and the whole episode has served to enhance what Paratici had been telling his contacts, that the new Spurs regime did not have much of a plan without him.

Tudor comes in with a clear challenge to keep Spurs safe from relegation. Three wins from 12 games should be enough and that is achievable, especially when players start to return from injury over the next month and onwards.

Igor Tudor comes in with a clear challenge to keep Spurs safe from relegation. Three wins from 12 games should be enough

Tudor will hope for more from Tottenham’s key men in the run-in, including summer signing Xavi Simons (pictured)

Venkatesham, though, must prove he has what it takes to run one of London’s finest and most illustrious clubs without Levy or Paratici there at his side. Not only to escape relegation but to hire a new head coach to launch a long climb back to respectability and convince fans there can be better times ahead in N17.

Unfortunately, it begins against Arsenal, the club where his reputation was built and their fiercest rivals, who just happen to be top of the Premier League and chasing four trophies.

All of it adds to the heat on Venkatesham. And without Levy, Paratici or Frank, he is exposed front and centre. Vinai and dry you might say.

The ex-Arsenal man who led Spurs into a relegation fight. He needs the Tudor spell to hasten success and find some solutions fast.