Despite managing for just 15 years, Antonio Conte has filled his trophy cabinet with nine major honours, including three league titles with Juventus and one with both Chelsea and Inter Milan.
But after leaving Italy in favour of a return to England, winning silverware with Spurs was always going to be a tough ask.
The north London side haven't won a trophy since the League Cup in 2008, and Conte was supposed to be the short-term fix that Spurs needed.
However, the Italian coach will endure a trophyless first season back in the Premier League, after Tottenham crashed out of Europe, the FA Cup and the League Cup this season.
As it stands, they're also facing an uphill battle to qualify for next season's Champions League, and Tottenham's patchy form has frustrated Conte in recent weeks.
Following a 1-0 loss to Burnley in February, Conte unleashed a scathing rant at the club, leaving many questioning his future in north London.
And while the 52-year-old coach tried to play it off as 'tactical', his latest quotes ahead of Tottenham's clash with Everton have resurfaced doubts over his future.
Conte stated that he is used to fighting for top honours, and said that not doing so at Spurs has been a "tough experience".
"Now this is a new challenge for me. For sure you need patience and you know at this moment you can't fight for something important, for what I am used to doing in my past and I think I deserved to do in the past.
"I deserved to stay and fight to win the league, to win trophies, because someone gave me something in my career.
"Now this is a new experience. I repeat, I am enjoying these months, we are fighting a lot because we are trying to change a lot of situations on the pitch and outside of the pitch. But if I get to be honest it is not easy.
"We are fighting, we are fighting to try and improve the situation, also because I think they ask of me this. I am trying to improve and give all of myself to try and change the situation.
"The situation is here for many, many years, not only at the last moment."
Conte also seemed to criticise the Tottenham board for not setting him any targets upon his appointment, something he said encouraged him to thrive at Inter Milan.
"I think that when Inter came to my house to ask me to go there, they asked me to win in two years and they gave me the possibility to do what I want," he said.
"I can tell you this. With Tottenham, honestly we didn't speak about this. Maybe the target is different because in Italy there was only Juventus, also Milan and Naples, but Juventus was the first to win nine titles in a row.
"When you know you only have one opponent and also the possibility of the club, you want to win in two years or three years.
"In two years we won and now Inter Milan is one of the best teams in Italy."
With Conte's history of resigning midway through his contract, Spurs fans are rightfully anxious of their Italian coach deciding to up and leave, but a strong end to the season would make all the difference to the mood around Tottenham.
They return to action on Monday evening, as they host a struggling Everton side in the Premier League.