Over nearly 25 years at the helm, Levy transformed Spurs’ fortunes off the pitch, built a stadium admired worldwide, and frequently flirted with glory on it.

But along with those achievements came controversies, criticism, and a legacy that will always be judged by what was built, and what was not.

From the Boardroom to the Top

Levy’s journey to becoming Spurs chairman began through ENIC (English National Investment Company), which gradually bought into Tottenham.

After acquiring approximately 27-30% of the club in late 2000, Levy replaced Alan Sugar as executive chairman in early 2001. Under his stewardship, ENIC eventually gained majority control by 2007, and the club was moved into private ownership in 2012.

The vision Levy carried was not just to compete, but to modernise. Spurs under Levy embarked on an ambitious programme to bring the club up to the standard of Europe’s elite: improvements to infrastructure, increases in revenue, and commercial expansion. But that vision would prove as much a test of patience as it was a triumph.

Achievements: Building More Than Just a Club

One of the first fruits of Levy’s tenure was silverware: in 2008, Tottenham won the League Cup, the only major domestic trophy in his earlier years. That win, while modest relative to the scale of expectations, offered proof that Spurs under Levy could deliver tangible success.

Arguably the most visible legacy is the Tottenham Hotspur Stadium. Completed in 2019, this vast, modern arena replaced the old White Hart Lane, not just as a home ground, but as a centrepiece for a transformed club identity.

It hosts concerts, NFL matches, boxing events, and thousands of fans each matchday, generating streams of revenue and global exposure.

Alongside that, the training complex at Enfield (Hotspur Way) rose under Levy’s leadership, offering one of the most advanced youth, medical, analysis and practice facilities in England.

Levy also consistently managed the finances with caution and commercial sense. Spurs under his leadership became one of the richest clubs in the world by revenue, placing regularly in the Deloitte Money League and avoiding many of the financial catastrophes that have befallen less prudent clubs.

While criticism often focused on lack of trophies, Levy’s ability to ensure financial stability, grow global brand appeal, and negotiate profitable player sales (Gareth Bale, Harry Kane, Luka Modrić among them) marked him as one of the Premier League’s most formidable executives.

On the pitch, there were also moments of near-glory. Spurs reached the UEFA Champions League final in 2019 under Mauricio Pochettino, and most recently (2024-25) lifted the Europa League, breaking a 17-year trophy drought.

Those successes, though unevenly spread, showed that Levy’s leadership could align with sporting achievement, yet always seemed just short of the greatest prizes.

Failures, Frustrations, and Unmet Ambitions

For all Levy’s off-pitch successes, many fans and pundits believe Tottenham underperformed on the field relative to its ambitions. Major domestic trophies, most crucially the Premier League title, remained elusive.

Despite multiple top-four finishes, the consistency required to challenge and overtake the dominant clubs in England was never fully achieved.

Managerial instability became a recurring issue under Levy. Throughout his reign, entrance and exit of managers followed often.

There were moments when high-profile appointments, Jose Mourinho, Antonio Conte among them, were expected to bring transformation, yet either failed to deliver or found themselves on short leash. Spurs’ 2024-25 campaign typified this frustration: lifting the Europa League came amid a dismal Premier League season, finishing 17th, and still led to another managerial change.

Perhaps most publicly resented was Levy’s perceived prioritisation of profit, negotiation, and infrastructure over bold investment in the squad.

His reputation as a tough negotiator is well earned, but many believe he pushed bargains too far, delaying or avoiding big spending that could have closed the gap to Spurs’ rivals. When fans chant “Levy out,” it was often less about him personally and more about the frustration of nearly-missed potential.

Legacy: What Will Levy Be Remembered For?

Daniel Levy’s legacy at Tottenham will not be simple; it will be complex, full of contrasts. For many, he will be the man who moved Spurs firmly into the modern era: from the old White Hart Lane to a breathtaking stadium, from middling finances to high revenue, from an occasional contender to a club that regularly qualifies for European competition.

He will be praised for his commercial vision, his unwillingness to overspend irresponsibly, and his patience, though for some that patience was patience delayed.

On the other hand, his legacy will also be marked by what was never quite achieved. The Premier League title slipped through Spurs’ fingers despite multiple solid campaigns.

Domestic cup success was rare. At times, the gap between ambition and results sparked discontent among fans, especially during seasons that oscillated between European triumphs and domestic disappointments. Managerial churn will likely be one of the more negative footnotes: many believe that with more stability, Spurs might have pushed harder for honours.

As Levy has stepped down in September, ushering in a new era with Vinai Venkatesham as CEO and Peter Charrington as Non-Executive Chairman, the foundations he laid give Tottenham a platform few clubs could claim.

Whether those foundations will allow the club to finally break its trophy-barrier more regularly remains to be seen. What is certain is that few executives in the modern era of English football can claim a tenure as long, as impactful, or as polarising as his.

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SSI’s formation comes just one month after Ilya Sutskever formally departed from OpenAI. His whereabouts were unknown until now when he broke his silence, introducing SSI as a mission-driven company with a singular focus on developing safe superintelligence. 

Alongside him are co-founders Daniel Gross, formerly of Y Combinator, and Daniel Levy, an ex-OpenAI engineer aiming to create a secure artificial intelligence system within a pure research organization, one which will be free from the distractions faced by other AI giants such as OpenAI, Google, and Anthropic.

Unlike its competitors, SSI will not chase after immediate commercial gains. Sutskever explained to Bloomberg that SSI’s first product will be the safe superintelligence itself. 

The company will not divert its attention to other products or services until this goal is achieved. In insulating itself from external pressures and competitive rat races, SSI aims to advance capabilities while ensuring safety remains paramount.

Sutskever is striving for AI safety. During his time at OpenAI, he helped to improve AI safety, collaborating closely with Jan Leike on superintelligent AI systems.

In a 2023 blog post co-authored with Leike, Sutskever warned that AI surpassing human intelligence could arrive within the decade — a development that demands solid research into control mechanisms.

SSI is in contrast to OpenAI’s original non-profit model. Designed from the ground up as a for-profit entity, SSI aims to attract capital without compromising its mission. While funding details remain undisclosed, the team’s credentials and the urgency of their mission reveal that SSI may soon be well-capitalized.

SSI operates from offices in Palo Alto and Tel Aviv. The company is currently recruiting technical talent to join its ranks. With a focus on huge engineering and scientific innovations, SSI aims to scale its works while maintaining a laser focus on safety.

Daniel Gross, one of SSI’s co-founders, sums up their approach as “Out of all the problems we face, raising capital is not going to be one of them.”

Flow enables businesses in the sector automate their processes and utilize social media marketing to scale and increase revenues.

The proptech’s customers include real estate agencies, developers, portals and CRMs who leverage the platform to connect individuals to properties and enhance brand visibility.

Flow automatically creates ads from business listings and brand profiles, linking them to their target audience on Facebook, Instagram, Google and Digital Billboards, to build brand and generate leads straight to agents’ mobile.

The funding will help Flow add other social media platforms such as TikTok and LinkedIn, as well as other advertising channels like out-of-home billboards to boost users’ businesses. Added to this, the funding will also go into Flow’s B2B growth strategy and the integration of its social media–driven real estate marketing platform into existing international property portals and CRM platforms.

The pre-Series A round was led by Futuregrowth Asset Management. Endeavor Harvest Fund and serial entrepreneur Steven Heilbron also participated, with existing investors such as Kalon Venture Partners, Vunani Fintech Fund and Buffet Investments.

Flow’s proptech marketing platform improves revenue for agents and experiences for property buyers and sellers. The startup revenues come from agents leveraging its SaaS platform and a percentage cut from their marketing spend. 

While Flow has had a 20% monthly revenue growth within the past year, it affirms to have over 300 clients using its platform, with almost 6,000 agents across South Africa, Namibia, Botswana, Mauritius and Australia. In partnership with property portals and CRM platforms, Flow plans to expand into Europe – France, Germany, Belgium and the UK.