From 2001 to 2025, Tottenham Hotspur was led by Daniel Levy, who oversaw a period in which the club missed opportunities to sign some remarkable players.
Whether it was Levy’s indecision over transfer fees or the choice of alternative signings, the north London side let slip a number of generational talents.
We’ve put together a starting XI of players that Spurs should have added to their ranks under Levy, arranged in a 4-2-3-1 formation.
GK: David Raya
Reportedly, Raya reached an agreement on personal terms with Spurs during the summer of 2023; however, the club ultimately opted for Guglielmo Vicario instead.
Spurs were reluctant to meet Brentford’s £40 million asking price for the Spaniard, who subsequently signed with their rivals Arsenal.
While Vicario has slowly become a less reliable goalkeeper, Raya has had two standout seasons at the Emirates.
RB: Jules Kounde
In 2021, Spurs showed significant interest in acquiring Kounde from Sevilla.
The French international was reportedly open to a move, but Levy chose to invest in Emerson Royal instead. Kounde later signed with Barcelona a year later.
Now considered one of Europe’s premier defenders, Kounde is part of a Barcelona squad aiming for a treble in the 2024-25 season, while Spurs continue to rely on Pedro Porro.
CB: Kim Min-jae
With South Korean star Son Heung-min already at Tottenham, the club felt confident about signing his international teammate, Kim, in 2022.
However, Kim opted for Napoli as he sought a team with more stability.
Spurs ended up bringing in Clement Lenglet instead, who had an unsatisfactory loan stint in north London.
CB: Milan Skriniar
Once again linked with Tottenham in 2025, fans hope Levy will be more successful in bringing the defender to England this time compared to five years prior.
Jose Mourinho had identified the Slovakian defender as his top choice in 2020, but Spurs hesitated at the £55 million fee set by Inter Milan.
Bringing in Joe Rodon for £11 million later in the window was a predictable outcome; Rodon now plays in the Championship with Leeds, while Skriniar has represented several leading clubs in Europe.
LB: Filip Kostic
Fresh off a Europa League victory with Eintracht Frankfurt in 2022, where he eliminated Spurs’ London rivals West Ham, Kostic was linked with a move to north London.
Antonio Conte sought to refresh his squad ahead of their Champions League return and eyed the Serbian for his crossing prowess.
As anticipated, Levy was not inclined to pay £25 million for a 29-year-old, and Kostic eventually joined Juventus instead.
Spurs went on to sign Ivan Perisic, a technically superior player, albeit one who was injury-prone and commanded high wages.
CM: Bruno Fernandes
The summer of 2019 saw a deal that could have transformed the Premier League fall through, leaving one of Europe’s top midfielders devastated.
Bruno Fernandes, then with Sporting Lisbon, was poised to join Spurs following their Champions League final appearance under Mauricio Pochettino.
Although a transfer fee was agreed upon, Tottenham and Sporting couldn’t finalize the agreement, forcing Fernandes to stay in Portugal for an additional six months.
He eventually moved to Manchester United in January 2020, rapidly establishing himself as one of the finest midfielders of his generation.
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CM: Joao Moutinho
In 2012, an extension beyond the transfer deadline was sought to finalize Moutinho’s move from Porto, but Spurs were unable to secure the deal.
A key target for Andre Villas-Boas after Luka Modric’s departure, Spurs had agreed on a £24 million fee and personal terms, but the transfer couldn’t be completed in time.
“We were prepared for the possibility of the deal falling through, considering it was a challenging club to negotiate with and would have been a club-record fee,” Villas-Boas noted.
“We have enough depth, and Moutinho’s transfer not going through should not overshadow our successful acquisition of (Clint) Dempsey.”
At least Spurs brought in Mousa Dembele a few days earlier, which proved beneficial.
RW: Eden Hazard
Reportedly rejecting offers from both Manchester clubs, Hazard acknowledged he considered Spurs’ interest in 2012 but ultimately decided against it once they failed to qualify for the Champions League.
“It’s true that Tottenham tempted me because it was a young team that placed third in the league,” Hazard stated.
“Unfortunately, the season’s conclusion did not go favorably, and they missed Champions League qualification, which swayed my decision.”
The club signed Gylfi Sigurdsson and Clint Dempsey that summer in their ongoing search for a No. 10, finally resolving their creativity issues with the acquisition of Eriksen the following year.
CAM: Rivaldo
In 2002, as Barcelona looked to reduce their wage bill, Rivaldo became available on a free transfer, prompting Levy to fly to Spain to express interest.
“This illustrates our high ambitions and preference for discreet operations,” manager Glenn Hoddle remarked.
“Sadly, it didn’t materialize this time, but the search continues.”
Rivaldo chose to join AC Milan, and Hoddle mentioned receiving a letter from the forward explaining his decision.
At least Spurs acquired another world-class playmaker that summer, in the form of Milenko Acimovic.
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LW: Khvicha Kvaratskhelia
That lingering sound accompanying PSG’s Champions League matches last year was the lament of Spurs fans over what might have been.
Kvaratskhelia’s performances captivated a continent tired of overly controlled football.
However, Spurs had the opportunity to sign the Georgian international long before his breakthrough at Napoli.
“Clubs were hesitant to invest €20 million on a player from a less prominent football country, as there was limited background information available,” his agent stated in November 2024.
Now just 24, Kvaratskhelia’s value has surged beyond £100 million following his move to PSG in January 2025.
ST: Sergio Aguero
Aguero scored 12 goals in 18 appearances against Tottenham during his tenure with Manchester City, amassing a total of 260 goals.
It’s difficult to envision the agile striker donning another English team’s colors, yet Levy fought hard to secure his signature in 2011.
Spurs had a £38.5 million offer for Aguero turned down, even though it matched the striker’s release clause.
Atletico Madrid still sought additional fees, so Spurs opted to withdraw, allowing Aguero to subsequently join their Premier League rivals that same year.
Reportedly, manager Harry Redknapp preferred to sign Diego Forlan for £10 million, a move Levy blocked due to the player’s age.
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