He may have finally left the club, but former Tottenham Hotspur chairman Daniel Levy often came under huge fire during his tenure for his actions off the field in North London.
The 63-year-old spent over two decades in the role, but was constantly called into question for his lack of spending to help improve the first-team squad.
He was undoubtedly part of the reason for the Lilywhites’ failures on the pitch, with the club even going 17 long years without a piece of silverware during his tenure.
Levy often became known for offloading key talents on the books of the club, something which once again led to anger from the supporters – especially given his lack of funding after such departures.
One player in particular was sold without an immediate adequate replacement being signed in the same window, which undoubtedly contributed to his demise in the role.
Levy’s decision to sell Harry Kane from Spurs
No Spurs fan would’ve predicted the success Harry Kane would have had for the first-team in North London, after he made his first Premier League start back in 2012.
The Englishman was an unknown quantity to many despite rising through the youth ranks, but rapidly adhered himself to the supporters with his form in front of goal.
He rapidly became a first-team regular, with his first major taste of success coming in the 2014/15 campaign, scoring 31 times in his 51 outings for the Lilywhites across all competitions.
Such a year would be the fourth-best of his time in North London, with his highest goalscoring year seeing him net a total of 35 goals – subsequently winning the Premier League golden boot that year.
As a result of his tremendous goalscoring record, the 32-year-old remains their highest ever goalscorer, with his total of 280 goals breaking the record set by the late Jimmy Greaves.
However, he was sold in the summer of 2023, subsequently joining German side Bayern Munich for a fee in the region of £82m – the second highest in their history.
Whilst they received a mammoth fee for his signature, no new centre forward was brought into the club until 12 months later, with Dominic Solanke costing a club-record £65m from Bournemouth.
However, the former chairman also made a huge mistake in allowing one other former player to depart the club, with the 63-year-old unable to land the reinforcements after his move away.
Levy’s biggest mistake whilst at Spurs
After such dismal years on the pitch for a prolonged period of time, it was hardly a surprise to see numerous top-level talents moving away for pastures new.
Just like Kane, numerous players caught the eye for the Lilywhites, including Kieran Trippier who has to depart and join Atlético Madrid to fulfil his ambitions of winning trophies.
The right-back racked up over 100 appearances in North London, but failed to win a single trophy – subsequently claiming the LaLiga trophy in his second year in Madrid.
He wasn’t the only player to move to Spain to take his career to the next level, with Gareth Bale making the leap and joining Real Madrid in a £85m deal in the summer of 2013.
His move remains a club-record fee received for a player, but such a deal left a huge hole in the club’s forward line and understandably so given his record in North London.
The Welsh international, who was dubbed “world-class” by John Hartson, scored 73 goals for the club before his big-money transfer, with his final campaign in the Premier League by far and away his best.
He netted 26 times in his 44 appearances for the Lilywhites, further highlighting the task the hierarchy had in trying to replace such a top-level talent.
In an attempt to do just that, Levy decided to fork out around £60m on the signatures of Roberto Soldado and Erik Lamela, but both ultimately failed to produce the goods in England.
The pair only scored 53 goals combined during their respective seasons at the club, with such a tally miles below the one Bale managed to achieve on his own.
21/22
20
11
2
12/13
33
21
8
11/12
36
10
13
10/11
30
7
2
09/10
23
3
5
08/09
16
0
0
07/08
8
2
1
Given his tally of 15 major trophies in Madrid, the player himself certainly made the right call in leaving the club, but it’s safe to say owner Levy should have tried harder to keep hold of the winger.
After seeing the replacements brought in to the club, there’s no question that Levy made a huge mess of the transfer, with such a decision one of his worst at the club.









