You cannot move to “win things”. What if he goes to City and they finish 2nd, make the semifinals of Champions League, runners up in a close league cup final and somehow crash out of the FA cup before being handed it. He’s had a good season, but won nothing. This is the reality. Great teams don’t always win.
The frankly brilliant 1986-87 Tottenham team won nothing. Coventry City did however win a major trophy. Who do you remember most ? Trevor Peake or Richard Gough ?
Kane moving might increase his chances of winning the league, but that’s all. The only guarantee is he will be paid more.
There is absolutely no reason at all that Spurs cannot win the FA Cup, League Cup, Conference League or finish in the Top 4. Will they? Perhaps not, but I can’t guarantee they won’t any more than I can guarantee City will.
So is this about the “big” trophies being the ones that count to Kane?. These are the hardest to win. City have never won the Champions League, why will they win it guaranteed in the next few years ? Liverpool beat city to the title 14 months ago, might happen again, who knows what comes next.
What does the move Guarantee ? M O N E Y. Not just for Harry, but millions for those around him too. It’s all about the money.