Tottenham could "fall apart" if they sold Harry Kane this summer, says former Spurs midfielder Jermaine Jenas.
Kane, 27, wants "honest" talks with Spurs chairman Daniel Levy with reports claiming he wants to leave this summer.
Jenas doubts whether Levy will be able to do enough in those talks to persuade the England captain to stay.
"The part of me that loves the club doesn't want Harry to leave," he said. "But he deserves his opportunity at the top and I hope he gets what he wants."
Speaking on BBC Radio 5 Live's Friday Football Social, Jenas added: "Levy has got to prove to Kane that what is coming in with regards to the manager, style of play and players over the next two seasons is going to be a team built to win something.
"And when I say win something, I don't think a League Cup cuts it with Harry Kane. We are not talking that any more, we are talking a team that can challenge for the title and a team that can be in the Champions League competing in the latter stages on a regular basis.
"If he sells Harry Kane - the stock of the football club, the look of the football club, they've lost the England captain, they've got no manager, they've got disgruntled players - what happens then to Son Heung-Min and a core group of players that have been successful at the football club? The whole thing falls apart and who holds that together?
"So Levy has got a lot of problems on his plate because on top of that he is trying to attract a manager, and to attract a top manager you want one of the best strikers in the world."
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Sources have told BBC Sport that Kane has not handed in an official transfer request but it is understood he thinks he has a gentleman's agreement that would allow him to leave this summer, having failed to win a trophy so far in his career.
The striker still has three years left to run on the six-year contract he signed in 2018, which would put Spurs in a strong position in transfer negotiations.
Jenas believes Kane's future will depend on the lengths he is prepared to go to try to force a move away.
"There are ways of forcing these moves and they are not pretty and it is the last resort," added Jenas.
"I have seen players do it. I have heard stories of players every time they get the ball in training booting it over the fence. I've heard horror stories of desks getting flipped over in manager's offices and all sorts. But I'm not sure Harry Kane is that type.
"If he has got it in him he can make it happen. I'm not sure he has."