It would be fair to say that Daniel Levy made some questionable and unpopular decisions during his mixed tenure as Tottenham Hotspur chairman.
Across the 25 years Levy was at the helm, Tottenham won just two major trophies, in part due to some strange appointments from Levy, who worked with 14 permanent managers during his time as chairman.
Of course, the 63-year-old does deserve credit for overseeing the move to an impressive new stadium, but football is ultimately a results business, and the former chairman was unable to achieve the expected level of success.
Here at Football FanCast, we have now ranked the five worst appointments Levy made during his time at the helm.
5 Andre Villas-Boas
Villas-Boas made his name as an exciting young manager during a very impressive spell with FC Porto, leading the Portuguese side to the title in an undefeated season, but he was unable to make his mark at Chelsea, lasting just over eight months.
As such, it was always going to be a gamble to appoint the at-the-time young coach, and some blunders in the transfer market meant he didn’t last particularly long at the helm.
Following the sale of Gareth Bale, the likes of Roberto Soldado, Paulinho and Vlad Chiriches failed to make the desired impact, and the trio did not last long in north London.
Games
80
Wins
45
Draws
18
Losses
17
Players used
43
While the Villas-Boas era wasn’t all bad on the whole, having only narrowly missed out on Champions League qualification in his first season, the humiliating 5-0 defeat to Liverpool and 6-0 loss against Manchester City in his second campaign means he enters this list in fifth.
4 Jacques Santini
In fairness, the appointment of Santini made perfect sense at the time. The Frenchman arrived at White Hart Lane off the back of a very impressive spell with Lyon, during which time he was awarded the “best French coach” award in 2002.
The former Lyon boss got off to a promising start at Spurs too, making an unbeaten start to the Premier League campaign. However, Santini had to make this list simply because of the length of his tenure.
Santini lasted just 13 games before handing in his resignation, citing personal problems as the reason for his exit, although it has since emerged that broken promises behind-the-scenes may have played a part, with the ex-Tottenham boss saying: “They promised me a big apartment on the beach and I found myself 200m from the sea with a view of my neighbours.”
Games
13
Wins
5
Draws
4
Losses
4
Players used
24
3 Juande Ramos
It may seem strange to name one of only two Spurs managers to win a trophy during the Levy era on this list, but the terrible start Ramos made to the 2008-09 season meant there was no way he couldn’t be included.
After winning the League Cup in 2008, the Spanish manager failed to kick on in the following campaign, picking up just two points from the opening eight games, which left Tottenham rock bottom of the Premier League table.
Consequently, Ramos’ reign is probably remembered more for that disastrous start than the success in the previous campaign, and his managerial career slowly went downhill following his departure from N17.
The Spaniard returned to his native country after leaving Tottenham, landing the Real Madrid job, but his stint at the Bernabeu was short-lived, being sacked after around seven months in charge, before going on to have another unsuccessful spell with CSKA Moscow.
Games
54
Wins
19
Draws
16
Losses
19
Players used
34
2 Jose Mourinho
Jose Mourinho is widely regarded as one of the greatest managers of all time for good reason, having been extremely successful during his time at Chelsea, Inter Milan, FC Porto and Real Madrid.
However, the iconic manager was clearly on the decline before Levy appointed him, having been dismissed by Manchester United after winning just seven of the first 17 games in the 2018-19 Premier League season.
Having won 26 trophies throughout his career as a manager, it is clear Levy viewed Mourinho as a born-winner, who could end Tottenham’s trophy drought, but the timing of the decision to sack him is the main reason he is included on the list.
With the former FC Porto boss, there is almost an expectation that the football won’t be great to watch, but he will win silverware. However, Levy made the bizarre call to pull the trigger just days before Spurs were set to play Manchester City in the EFL Cup final.
Tottenham were left to rue the decision, going on to lose the game 1-0 under the helm of Ryan Mason, with Levy later going on to admit it was an error to appoint Mourinho in the first place, saying: “The strategy was to bring in a trophy manager and we did it twice. You have to learn from the mistakes.”
Games
86
Wins
45
Draws
17
Losses
24
Players used
44
1 Nuno Espirito Santo
Like the majority of the names on this list, Nuno is by no means a bad manager, having gone on to prove himself at Nottingham Forest, leading the Tricky Trees to the Europa League after finishing 7th in the Premier League last season.
However, the 51-year-old felt doomed from the start, with Spurs well-known to have made approaches for a number of other managers before having to ‘settle’ for the former Wolverhampton Wanderers boss.
The Portuguese manager actually went on to start the season very well, winning his first three matches, but results soon went downhill, and he didn’t last long, with Levy ultimately dismissing the now Forest boss at the beginning of November.
Jamie Carragher went on to suggest that Nuno’s style of play meant the appointment was simply never going to work out, saying:
“I can never justify a manager losing his job after 10 Premier League games, it doesn’t feel right, but I don’t think Nuno at Spurs ever felt right either.
“I don’t feel this is a bad sacking, I think it was a bad appointment initially. Nuno’s style of football was at odds not only with the ‘Tottenham way’ but also the ‘top-club way”.
Games
17
Wins
9
Draws
1
Losses
7
Players used
30
With Levy now gone, Tottenham fans will be hoping that this is the beginning of an exciting new era for the club.
