Ranking of Daniel Levy’s worst appointments in Tottenham

It’s safe to say that Daniel Levy made some questionable and unpopular decisions during his mixed tenure as chairman of Tottenham Hotspur.

With Levy at the helm for 25 years, Tottenham won two major trophies. This is the collaboration with 14 permanent managers as chairman for a strange appointment from Levy.

Of course, the 63-year-old deserves credit for overseeing the transition to an impressive new stadium, but football was ultimately the outcome business, and the former president failed to achieve the expected level of success.

Here at Football FanCust, we ranked five worst appointments Levy had at the helm.

5

Other Villa Boa

Villas-Boas named him as an exciting young manager in a very impressive spell with FC Porto, leading the Portuguese side to the title in an undefeated season, but he couldn’t last just eight months at Chelsea.

So, appointing a young coach of his time would always be a gamble, and the transfer market’s surges meant he didn’t last long, especially at the helm.

Following the sale of Gareth Bale, Roberto Soldad, Paulinho, Vlad Chilichs and others were unable to make the desired impact, and the trio did not last long in North London.

While Villas-Boas’ days weren’t bad overall, he missed just a small miss out on Champions League qualifying in his first season, and a humiliating defeat to Liverpool and a 6-0 loss to Manchester City in his second campaign meant he would be on this list in fifth place.

4

Jack Santini

To be fair, Santini’s appointment made perfect sense at the time. The Frenchman arrived at White Hartrain from behind a very impressive spell with Lyon, during which he received the “Best French Coach” award in 2002.

The former Lyon boss also got off to a promising start for the Spurs, making his Premier League campaign an invincible start. However, Santini had to make this list for the length of his tenure.

Santini played just 13 games in the row before handing over his resignation. I cited personal issues as reasons for exit, but it is possible that the broken promises have played a role behind the scenes ever since. “They promised me a big apartment on the beach and I found myself 200 metres from the ocean, looking out at the views of my neighbors.”

3

Juande Ramos

It may seem strange to name one of the two Spurs managers to win the trophy during this tax age on this list, but the terrible start Ramos made in the 2008-09 season meant there was no way he wasn’t included.

After winning the League Cup in 2008, the Spanish manager failed to kick on in his next campaign, scoring just two points from the opening eight games, leaving Tottenham Rock Bottom at the Premier League table.

As a result, Ramos’s reign was probably remembered for a more disastrous start than his previous campaign success, and his management career went slowly downhill after his departure from the N17.

The Spaniard left Tottenham and returned to his home country after winning a job for Real Madrid, but his stint at the Bernabeu was short-lived and was fired about seven months later, before winning another failed spell with CSKA Moscow.

2

Jose Mourinho

Jose Mourinho is widely regarded as one of the greatest managers of all time for good reason, and has been extremely successful in Chelsea, Inter Milan, FC Porto and Real Madrid.

However, the iconic manager was clearly in decline before Levy appointed him. He was fired by Manchester United after winning seven of the first 17 games of the 2018-19 Premier League season.

Winning 26 trophies throughout his career as a manager, it is clear that Mourinho is considered a born recipient.

The former FC Porto boss has mostly hopes that football doesn’t look very much, but he wins silverware. However, Levi made a strange call to pull the trigger a few days ago for the Spurs to play Manchester City in the EFL Cup final.

Tottenham lost the decision and continued to lose the game 1-0 under the helm of Ryan Mason. Later, Levi admitted that it was wrong to appoint Mourinho in the first place, saying: “The strategy is to introduce a trophy manager, and we did that twice. You have to learn from the mistakes.”

1

Nuno Espirito Santo

Like most names on this list, Nuno was by no means a bad manager, continuing to prove himself in Nottingham Forest, leading the tricky tree into the Europa League after finishing seventh in the Premier League last season.

However, the 51-year-old felt destined from the start. The Spurs are well known to have approached many other managers before they had to “settle” them into the former Wolverhampton Wanderers boss.

The Portuguese manager actually started the season very well, winning his first three matches, but the results quickly went downhill and he didn’t last long.

Jamie Carrager went on to suggest that Nuno’s theatrical style simply meant that the appointments were not going well, and that:

“You can never justify the manager losing his job after 10 Premier League matches. I don’t feel that’s right, but the Spurs’ Nuno doesn’t feel right either.

“I don’t think this was a bad loot. I think it was a bad booking at first. Nuno’s style of football was “conflict with Top Club Way,” not just “Tottenham Way.”

With Levy gone, Tottenham fans hope this is the beginning of an exciting new era for the club.