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Excellent questions.
A: He will win nothing with Spurs.
B: He wants to play in the Premier League and no other top club is set up perfectly for him to be first choice.
C: This is the major hurdle. You have to think that Levy wouldn't be willing to lose Kane on a free. Kane will have the opportunity to run down his contract if Levy denies him a move. I think he will play hardball, but a bid of 100+ million would be enough to tempt him to sell.

And you think he’ll win something at United?

Jeez, you guys have a good couple of months and all of a sudden you’re world beaters who can guarantee silverware. Delusions of grandeur…

I think it’ll come down to whether Spurs qualify for the Champions League. If we do, he’s not going to be banging down Levy’s door for the chance to join United and most likely he’ll sign a new contract. If we don’t, it’s 50/50.

I know he will win nothing with Spurs, that's for sure. 😁
If he signs a new contract just because of finishing in the top 4, he definitely deserves to retire trophyless. Your squad is so poor. Conte has suggested it will take 3 to 4 windows, which is about two years.

Kane will be 32 and he will definitely have locked himself out of a top move.

Look, if you are being truthful to yourself, you would admit Kane needs to move on somewhere. It doesn't have to be United. #FreeKane.