Tottenham chairman Daniel Levy is currently the longest-serving chairman in the Premier League having enjoyed 20 years at the reins in north London.In that time, he has had to make a few difficult managerial decisions, including one this summer as he appointed Nuno Espirito Santo as Jose Mourinho’s successor. In all, Levy has appointed and let go of nine different managers in his time involved with Spurs, with a number of them having differing fortunes during their periods in charge.
Glenn Hoddle
The first man to be appointed by Levy, Hoddle returned to Spurs in 2001. He oversaw 101 matches in his time in north London before eventually being sacked in September 2003. Since his spell with Spurs, the Englishman spent a period with Wolverhampton Wanderers, whilst he also returned to the game in 2014 to become assistant manager at Queens Park Rangers. He has not held a position in football since then and instead has become a pundit. Intriguingly, he was recently seen on The Masked Singer, eventually finishing in ninth place.
Jacques Santini
Previously the manager of the French national side, Santini became Hoddle’s successor after Euro 2004. However, his spell was short-lived as he only led the club for 13 matches in all competitions before announcing his resignation. He then returned to his home country with Auxerre but again was let go after a short while and has not returned to the dugout since.
Martin Jol
Previously part of Santini’s backroom staff, Dutchman Jol was promoted to the main role after the former’s resignation. He led the club for just under three seasons, and oversaw an impressive rise up the Premier League table. His initial success did not continue and he was eventually sacked in October 2007, when he moved on to Hamburg. Spells with Ajax, Fulham and Al Ahly followed and he is now back in the Netherlands acting as ADO Den Haag’s technical director.
Juande Ramos
In charge of Tottenham for just under a whole calendar year, it would be fair to say that the Spaniard fell upwards after his exit from north London. He took the reins with Spanish giants Real Madrid following his sacking but lasted just 27 matches, whilst a following spell in charge of CSKA Moscow ended after just nine matches. Ramos then enjoyed slightly more success with Ukrainian outfit Dnipro, building the foundations of a side that would eventually reach the final of the 2015 Europa League. He then had another short spell with Malaga and has been out of work since.
Harry Redknapp
A name popular with fans of the Premier League, Redknapp’s stint with Tottenham was just one stop on his wide-ranging exploration of English football. After leading the club back into the Champions League, the Englishman departed in 2012 and was subsequently appointed at Queens Park Rangers and Birmingham City, whilst he also had a spell in charge of the Jordan national team. Redknapp officially announced his retirement in 2017 and has since appeared on I’m A Celebrity Get Me Out Of Here, where he was named the winner.
Andre Villas-Boas
Following a disappointing spell with London rivals Chelsea, Portuguese head coach Villas-Boas was handed a three-year deal with Spurs. He slightly recovered his reputation with Tottenham having overseen 80 matches in all competitions, winning 44 of those. Levy made the decision to sack Villas-Boas in December 2013 following a poor start to the season and he has had spells with Zenit St Petersburg, Shanghai SIPG and Marseille. He exited the French club earlier this year and has since pursued a career in motorsport, having appeared in the World Rally Championship.
Tim Sherwood
Initially appointed on a temporary basis, the former midfielder was handed an 18-month contract. He did not have the chance to complete that deal though, as he was sacked by Levy at the end of the campaign, with Spurs having finished sixth. Sherwood was appointed at Aston Villa as a replacement for Paul Lambert and despite leading the club to the FA Cup final, was sacked just eight months later. The 52-year-old has since had a spell as Swindon Town’s director of football and has also worked as a pundit.
Mauricio Pochettino
Arguably Spurs’ most successful manager in the Premier League era, Pochettino joined from Southampton and masterminded a dramatic transformation in north London. He led the club to four consecutive top-four finishes, whilst also booking Spurs a place in the 2019 Champions League final against Liverpool. However, his spell turned sour and he was replaced by Jose Mourinho. After being out of work for a while, the Argentine was then appointed at Paris Saint-Germain and has since won the Coupe de France. He also now has the likes of Lionel Messi, Kylian Mbappe and Neymar at his disposal in the French capital.
Jose Mourinho
Expected to bring success to north London, Mourinho’s spell with Spurs did not go as positively as his experiences with Chelsea. He got Spurs back on track after the sacking of Pochettino and even reached the Carabao Cup final, only to be sacked a couple of days before the Wembley showpiece. Mourinho worked as a pundit before his appointment at Roma earlier this year and has the Italian club sitting fourth in the Serie A standings after seven matches of the current campaign.