It was the end of an era last week when Tottenham Hotspur officially confirmed that Daniel Levy would be stepping down as chairman after more than 24 years at the helm.
The highlight of his tenure at the football club arguably came earlier this year when Ange Postecoglou led the club to the Europa League trophy, beating Manchester United 1-0 in the final.
Away from results, as much as supporters may not want to hear about it, Levy also made significant progress on the financial side of the club during his time as chairman.
Football finance expert Kieran Maguire recently claimed that he ran the club “very efficiently” and noted that Spurs make ten times as much in revenue as they did when he arrived in March 2001.
As you can see in the post above, Tottenham were the most profitable ‘big six’ club in the Premier League over the past 24 to 25 years, and one of only three of those six teams to be profitable at all.
Whilst there may be some criticism over some of the signings made by Levy, including the likes of Tanguy Ndombele and Davinson Sanchez, the ex-Spurs supremo also made some terrific signings.
Some of Daniel Levy's best Tottenham signings
Gareth Bale is the first name that comes to mind when thinking about his best signings for Tottenham, given what he went on to achieve after joining.
Spurs reportedly paid a fee of £10m to sign the Welsh wizard from Southampton in the summer of 2007, after he registered 11 assists in the Championship for the Saints, per Transfermarkt.
Bale went on to establish himself as a superstar in North London with 30 goals and 17 assists in his last two Premier League seasons, per Transfermarkt, before his world-record £85m move to Real Madrid in 2013.
Heung-min Son, who captained the club to the Europa League trophy earlier this year, is also another one of the most impressive signings Levy made for Spurs.
Tottenham signed the South Korea international from German side Bayer Leverkusen in 2015 for a fee of £22m, after he had scored 29 goals in 87 appearances for the German side, per Transfermarkt.
24/25
46
11
23/24
36
17
22/23
47
14
21/22
44
24
20/21
49
21
19/20
41
18
18/19
48
20
17/18
53
18
16/17
47
21
15/16
36
7
As you can see in the table above, the former Spurs captain provided a consistent threat at the top end of the pitch as a goalscorer throughout his ten years in North London.
Son was a brilliant signing, therefore, because he was an incredible servant for the club for a decade, and captained the team to a major trophy this year.
Bale and Son were phenomenal signings for Spurs by Levy for slightly different reasons, as the former earned the club a huge profit and the latter delivered huge success for the team on the pitch by winning a trophy.
Levy’s best signing during his time at the club may not be Bale or Son, though, because that award may go to the deal that brought Dele Alli to North London.
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Football is an incredibly subjective sport and a lot of supporters like to have their say on who the club should target and sign to bolster the squad based on their own views.
The deal to sign Bale, who had just delivered 11 assists in the second tier for a fairly big club like Southampton, and the deal to sign Son, who had scored 29 goals in Germany already, were ones that fans could have pointed out and asked for.
Why Dele Alli was Daniel Levy's best signing for Tottenham
Dele was an even better signing than Bale and Son for Spurs because of the nature of the deal, given the price tag, where he came from, and what he went on to achieve.
Levy swooped to sign the attacking midfielder from League One side MK Dons for a fee of £5m at the start of 2015. This was a bold move by the Spurs chief because he had only played League One football up to that point.
He also became the first player MK Dons ever sold to a Premier League team for more than £1m, per Transfermarkt, which shows that he was not coming from a team, like Southampton, with a rich history of developing young talent.
The teenage talent had scored 24 goals and provided ten assists in 88 games for the League One team, fewer goals than Son managed for Leverkusen and fewer assists than Bale produced for the Saints, but made the step up to the Premier League in the 2015/16 campaign and hit the ground running.
Alli scored ten goals and provided eight assists in 33 games in the top-flight in the 2015/16 season, which was a remarkable achievement given that he came straight from the third tier.
He won the PFA Young Player of the Year award in both of his first two seasons with Spurs, becoming one of a select few to have won the award twice, and provided consistent quality on the pitch for several years.
Attacking midfield
158
42
40
Central midfield
48
9
5
Left midfield
36
14
8
Centre-forward
8
2
1
Defensive midfield
2
0
2
As you can see in the table above, Alli provided goals, assists, and positional flexibility for Spurs throughout his time at the club, with 67 goals and 59 assists in total.
Alli, who was described as a “pure wonderkid” by talent scout Jacek Kulig looking back on his form for MK Dons, may not have had a picture book ending to his career at Spurs, signing for Everton on a free transfer in 2022, but there is no doubt that he was an incredible signing for the club.
The England international was Levy’s best piece of business during his time at the club because of how obscure the signing was, given the league he was playing in and MK Dons’ lacklustre history when it comes to selling young talent.
It was a risky move by the chairman and one that paid off almost immediately on the pitch, as evidenced by his PFA awards, and that is why Levy can look back on that signing as his best piece of work.