Tottenham’s expected replacement of Nuno Espirito Santo with former Chelsea boss Antonio Conte could present Manchester City with a January transfer dilemma.
The Blues ’ summer pursuit of England skipper Harry Kane ran into the brick wall of Spurs chairman Daniel Levy’s stubborn intransigence, despite the player making it perfectly clear that he wanted to leave – and that City were his intended destination.
Levy eventually refused to even discuss a fee for Kane, leaving City to begin the season with no recognised strikers, after the departure of Sergio Aguero for Barcelona in the summer.
Signing a striker remains their priority in the next year, and they were expected to get through this campaign and then weigh up their options next summer, when Borussia Dortmund sensation Erling Haaland may be available, with suggestions that he has a £68million release clause in his contract which will become active at some point next year.
That would mean the 21-year-old, who is a City fan, could cost the Blues around half of the projected fee for Kane.
But the arrival of Conte as Spurs boss makes it a distinct possibility that Tottenham could decide to finally give in and allow Kane to leave in January.
The striker has been in poor form for the London club and is believed to be one of the stars who Nuno was talking about when he criticised a lack of effort from some of his squad last week.
If that is Kane’s message to Levy and the club hitting home, it means Conte has a big decision to make once he takes the reins at White Hart Lane.
Nuno was in a no-win situation when he took over in the summer, in the middle of the stand-off between Levy and Kane, who is believed to have been angry that the chairman did not honour what he says was an agreement that he could leave if things did not work out after signing a deal which ties him down until 2024.
That could explain the poor form that has seen him score just one Premier League goal this season.
And today, former Spurs player Jamie Redknapp has urged Conte to confront the problem head on.
The former England midfielder, when asked what Conte’s first job was, said: “Get Harry Kane going. That’s the big thing. If I was the manager of that club right now and took over the job, how do I get Harry Kane going?
“You need to have a conversation with him — ‘How do you feel about being at this club? Do you want to be here? Are you part of my plans?’
“If he says no, I’d try to sell him in January. If he doesn’t want to be there you’ve got to look at the situation where you’re going to give it all for me and get back to the level.
“I’m his biggest fan, Harry, but he’s not playing to the level that he wants at the moment. He doesn’t look like he’s enjoying his football.
“That would be your first objective — can I get Harry Kane playing well alongside Son, get a system that works for the players and make sure you get that level back.”
Nuno did not have the luxury of tackling the Kane issue. He could not be seen to walk straight into a row with the club’s star player, and was not in a position to tell Levy that he needed to sell.
But with a suggestion that the dressing room is unhappy — with Kane one of the most disgruntled — Conte is in a far stronger position.
The man who took Chelsea to their last league title in 2017 and guided Inter Milan to their first Serie A title for 11 years, is in a position of strength.
The fans can see that Kane is nothing like the player he was, and the prospect of getting a £100million fee for him looks a lot more attractive now than it did four months ago.
Conte is known for being a manager who will take no nonsense, does not respect reputations and will root out anything that challenges his control.
He said after taking charge at Chelsea: “The coach must be in total control of the dressing room otherwise there is anarchy.”
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If Conte thinks Kane is now the club’s biggest problem rather than their main asset, he will not hesitate to take Redknapp’s stance and suggest to Levy that they cash in while they can.
Unless they ask an unrealistic fee, that would certainly arouse City’s interest again; the idea of having Kane for the second half of the season is a tempting one.
The fact that his participation in the Europa Conference League group stages will no longer disqualify Kane from playing in the knockout phase of the Champions League — should City qualify — is an added bonus.
Weighed against that is the possibility of bringing in Haaland instead, if they can wait for six months.
The truth about the release clause is not evident, but if Haaland is going to be available, it is a major temptation to forget Kane and go for the younger man in summer.