For one of the stars of England's summer, it was a move he couldn't turn down.
"I obviously spoke to the staff and players before I left but I had to stop towards the end because I was going to cry a little," the multi-million pound asset told Sky Sports.
"But it was something I couldn’t turn down.
"I read something about Michael Owen when he left ( Liverpool ) for Real Madrid and he said if he didn’t move he would regret it and I didn’t want to feel the same."
And so with that he was gone. Jack Grealish was a Manchester City player.
Grealish's £100million move from his boyhood club Aston Villa was one of the sagas of the summer, but it was one for which you sensed the ending was always written.
Villa were desperate to keep hold of their captain, but such is the food chain of the football world then they were always going to have trouble fending off the advances of City, who could dangle enough temptation in front of Grealish that he would eventually feel compelled to accept.
For Harry Kane things have been rather different.
The forward's longed-for trophy success with Tottenham might never have materialised, but he has been in touching distance of it before. While for England in the summer he was a couple of penalty kicks away from being the captain who lifted the first major prize for 55 years.
Kane has had a wonderful career, whatever happens from this point on.
His failure to join City this summer can end up being put down to City themselves, who were unwilling to pay the asking price for a player they wanted a lot - just clearly not quite enough.
But with Pep Guardiola now claiming that he will in all likelihood leave City in the summer of 2023 - something which sounds light years away but is actually just the end of next season - suddenly Kane is left confronting the reality he had been desperate to try and avoid.
Asked where his next role would be during an event on Wednesday, Guardiola let slip when he sees himself in the future.
"A national team, yes," he said
"Next step will be a national team, if there is a possibility. A national team is the next step.
"I must take a break after seven years (at City). I need to stop and see, learn from other coaches, and maybe take that path.
"I would like to train for a European Championship, a Copa America, a World Cup"
So with just one more summer of Guardiola at City - the preparations for the 2022-23 season next year - then has Kane just missed out on his best chance of guaranteed trophies?
If the Catalan doesn't sign him next summer then he won't have a chance the summer after, when the forward will be 30 and doubtless see his options dwindling.
Of his other serious suitors then Chelsea disappeared off the table the moment they signed Romelu Lukaku, and while Manchester United could afford him there are still serious questions over their capability to win things under Ole Gunnar Solskjaer.
Real Madrid and Barcelona are a bit preoccupied now, and Paris Saint-Germain are fully stocked.
So with England success just narrowly escaping him this summer, it would appear as though guaranteed glory has slipped from the forward's fingertips.
He'll have always preferred to win things with Spurs anyway though, and so that has to be his motivation heading into this season and the years to come.
It would quite simply mean more to him.
Kane x Guardiola might never be, but Kane x Glory is still a possibility.
