Daniel Levy is facing his toughest summer in charge of Tottenham Hotspur with the futures of head coach Antonio Conte, managing director of football Fabio Paratici and record goalscorer Harry Kane all coming to a head.
It is now rated as inevitable that Conte will leave Tottenham, but that is just one of a number of huge problems piling up for Levy, which include:
The future of Paratici, with an Italian court date set for the end of the month to decide whether he could be part of a criminal trial into alleged tax and salary malpractice at his former club Juventus.
The future of Kane, who has reiterated his desire to win trophies and is not expected to hold talks about his contract before the summer, when he will have 12 months to run amid interest from Manchester United.
Whether to ignore doubts from inside the club to re-hire Mauricio Pochettino or explore alternative managerial targets likely to include Luis Enrique, Ange Postecoglou, Roberto De Zerbi and Luciano Spaletti.
Levy, the Tottenham chairman, must also address an astonishing outburst from summer signing Richarlison, who could face a fine for speaking out against Conte and describing his season as “s—“, and disillusionment from within the club’s academy.
A source told Telegraph Sport: “Daniel Levy has gotten himself out of some difficult positions in the past, but this is different, the problems are too big and there are too many.”
Having been eliminated from the Champions League by AC Milan, Tottenham have no immediate plans to sack Conte, who is due to take charge of the team for Saturday’s Premier League visit of Nottingham Forest.
But insiders believe it is now “inevitable” that Conte will leave, whether it is at the end of the season when his contract expires or even earlier should fourth-placed Tottenham fall away in the race to qualify for next season’s Champions League.
Conte came under fire from Richarlison, with Tottenham not offering any comment on whether or not the Brazilian will be fined for revealing his anger at not starting against Milan.
“This season, excuse the word, it’s been s—, because I don’t have minutes, I suffered a little with the injury,” Richarlison, who joined Spurs in a deal worth £60 million last summer, told TNT Sports Brazil. “But, when I enter the field, I give my life. I came from two games well, I think that’s it, I think I should have played and I don’t have to cry about it.
“It was going well, in a good sequence, two wins against West Ham and Chelsea. Suddenly, he put me on the bench, against Wolverhampton he put me on for five minutes. I asked why? They didn’t tell me anything.
“And, yesterday, they asked me to take a test at the gym, that if I was good I would go to the game and, at the time of the game, they left me on the bench. These are things that it is not possible to understand.
“Let’s see what he (Conte) will say tomorrow, but there are no fools here either, I’m a professional, I work every day and I want to play. There are minutes left, time left.”
Pochettino, who was sacked by Levy almost four years ago, is believed to be open to the prospect of a return, but that is not a prospect that would automatically receive the overwhelming support of key decision makers within Spurs.
While Levy could save himself from the possibility of facing even more criticism from fans by re-appointing Pochettino, there remain fears over whether it would be wise for the Argentine to go back having only managed at Paris Saint-Germain since being sacked.
Levy will consider a list of alternative potential targets that will include Enrique, who was sacked by Spain after the World Cup, Celtic manager Postecoglou, Brighton’s De Zerbi and Napoli boss Spalletti, and take suggestions from Paratici.
But the role of Paratici, who is already waiting to find out whether or not a ban in Italy will be extended across the world, could be further complicated by an Italian court case that is scheduled for March 27.
Paratici was handed a 30-month ban from Italian football as part of the sanctions imposed on his ex-club Juventus by the Italian Football Federation, which could still be applied across the globe.
On March 27, a preliminary hearing of a criminal investigation into the capital gains and salary maneuvers of Juventus and individuals who worked at the club, in which Paratici has been named among the defendants, will take place to decide whether or not a trial should go ahead.
As previously reported by Telegraph Sport, Kane is being urged to leave Tottenham this summer with the striker yet again unable to win his first trophy with the club.
“Where we’re at as a club, we should be winning trophies,” said Kane. “That’s always the aim. The top four [being our only target] is a consequence of not playing as well as we want to play.
“Now that’s all we can fight for [top four] so that’s going to be the goal and hopefully we can achieve that. But for sure, it’s not enough for this club.”
On Conte’s future, Kane added: “It’s his decision, he’s going to be the one who makes that choice. All we can do as players is try to perform for him, work as hard as we can. That’s what we’re doing. You can’t fault the effort of the players.”