Daniel Levy’s departure from Tottenham Hotspur was a seismic announcement that rocked not just the club, but football as a whole.
Levy was previously the longest-serving chairman in the division having assumed the role in 2001. And he’s delivered a new stadium and world class training facilities, while established the club as a global brand.
Fans will look to the lack of squad investment as a stick with which to beat Levy. But the former Tottenham supremo has previously dipped his hand into his pocket to invest in the squad — albeit not as readily as some may hope.
So the question is, how well have Tottenham’s most-expensive arrivals under Levy fared (using fees from Transfermarkt)?
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10. Archie Gray
- Arrived: 2024
- Fee: €41.25m
Archie Gray looked to be on the cusp of a move to Brentford last summer. But Tottenham swooped in at the last minute to steal the youngster from the Bees.
As one of the most promising teenagers in the country, Spurs did well to ultimately lure the midfielder to north London. Gray, though, hasn’t really been handed a chance to consolidate a starting spot in his favoured midfield role. Injuries saw the 19-year-old forced to largely play centre-back under Ange Postecoglou and he’s made just one start under Thomas Frank this season.
Verdict: Too early to tell
9. Davinson Sanchez
- Arrived: 2017
- Fee: €42m
Tottenham finished second in the Premier League in 2016-17 under Mauricio Pochettino and boasted the best defensive record in the division, conceding just 26 league goals. There were unbeaten in their final season at White Hart Lane, and wanted to make a statement signing to mark their move to Wembley.
Davinson Sanchez was part of the Ajax side that lost the 2017 Europa League final, yet Tottenham saw enough to splash the cash. The Colombian was added to the ranks as Pochettino sought to continue with a three-man defence. Sanchez initially impressed alongside Toby Alderweireld and Jan Vertonghen, maximising his impressive recovery pace that saw Tottenham enjoy another commendable campaign. However, the 29-year-old’s shortcomings eventually came to the fore before he departed as a figure of fun for Galatasaray in 2023.
Verdict: Miss
8. James Maddison
- Arrived: 2023
- Fee: €46.3m
Tottenham beat Newcastle United to the signing of James Maddison in 2023, with Harry Winks going the other way to Leicester City. Few expected Maddison to turn down a switch to St. James’ Park for the Tottenham Hotspur Stadium two years ago, and his arrival was welcomed with open arms.
The issue has been that the England international has been dogged by injury problems, most recently suffering a season-ending ACL injury in pre-season. Yet Maddison was key to Tottenham’s progression to the Europa League final last season. And while he may not feature for the club this season, he’s still proven a successful addition.
Verdict: Hit
7. Cristian Romero
- Arrived: 2022
- Fee: €52m
When Tottenham were tentatively linked with a move for Cristian Romero in 2022, it was treated as nothing more than a pipe dream. However, that dream became reality that summer as Spurs secured the Argentine’s services on an initial loan before the deal was made permanent in 2023.
Romero has drawn some criticism from the fanbase for a lack of availability with a clear preference to turn out for Argentina. But he proved his worth as Spurs won the Europa League back in May. In the time since, Romero has signed a new deal and been made captain following Son Heung-Min’s departure.
Verdict: Hit
6. Brennan Johnson
- Arrived: 2023
- Fee: €55m
Brennan Johnson is the most frustrating player on the Tottenham books. For 89 minutes and 59 seconds, the Welshman will offer little on and off the ball, but will suddenly pop up with a goal.
Take his header in the semi-final win over Bodo/Glimt for example. Or key league goals against Brentford, Brighton and Manchester City. and his winner against Manchester United in Bilbao back in May.
The forward does nothing of note before doing what he does best – putting the ball in the back of the net. Many questioned why Tottenham splashed the cash for the 24-year-old in 2023 but the first-half strike in the Europa League final means he’s more than made up for the hefty fee to sign him from Nottingham Forest.
Verdict: Hit
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5. Richarlison
- Arrived: 2022
- Fee: €58m
Richarlison arrived to great fanfare in 2022, even if he commanded a significant fee to sign from Everton. Finally Tottenham had cover across all key positions on the frontline in Antonio Conte’s favoured three-man backline.
Yet the Brazilian struggled for game time under the Italian and he scored just one league goal, which came in a late 4-3 loss at Liverpool. The striker is a likeable character but has struggled with injuries that has limited his impact in the capital. Richarlison has started the season strongly and is a fan favourite, but equally; he’s a modern-day sicknote, which means it’s still tough to determine whether he’s a hit or a miss.
Verdict: Jury still out
4. Tanguy Ndombele
- Arrived: 2019
- Fee: €62m
Tanguy Ndombele was the most exciting midfielder on the continent before he moved to Tottenham in 2019. Many viewed the Frenchman as the natural heir to Mousa Dembele in the Spurs midfield given his ability to ghost past an opponent.
Ndombele started off well, scoring on his debut in a 3-1 home win over Aston Villa. However, no matter the manager, the France international struggled for consistency and fitness. An unmitigated disaster of a signing, his contract was mutually terminated last summer.
Verdict: Miss
3. Mohammed Kudus
- Arrived: 2025
- Fee: €63.8m
Having lacked direct wingers last season, Tottenham made amends with the addition of Mohammed Kudus over the summer. The Ghana international spent two years at West Ham and while his move to the Hammers’ rivals has left a bitter taste in the mouth, Kudus has already become a favourite with the Tottenham fanbase.
He has two assists to his name from his opening three games, and ranks second to Yankuba Minteh (11) for successful take ons (9) in the Premier League this season. The early signs have been positive.
Verdict: Too early to tell
2. Dominic Solanke
- Arrived: 2024
- Fee: €64.3m
The pressure was on Dominic Solanke to succeed from the moment he arrived. Tottenham hadn’t properly replaced Harry Kane, who left for Bayern Munich in 2023, and the big money addition of Solanke was expected to ease the burden on the likes of Son Heung-Min, Brennan Johnson and Richarlison.
The towering frontman has struggled with injuries during his time at the club, which has impacted his hopes of consistency, and means he’s scored just nine league goals to date. For the fee spent to secure his services, the 27-year-old could well be considered a miss.
Verdict: Miss
1. Xavi Simons
- Arrived: 2025
- Fee: €65m
Having missed out on Morgan Gibbs-White and Eberechi Eze, Tottenham turned their attention to Xavi Simons in the dying embers of the transfer window. The Dutchman was heavily linked with a summer switch to Chelsea, even if the Blues never lodged an official bid for the Dutchman’s services.
Fans are excited about the arrival of Simons. But having signed after the registration deadline, they’ll have to wait a little longer for their first glimpse of the 22-year-old in a Tottenham shirt.
Verdict: N/A