The first question is whether Spurs will let their talisman go. If so, it then becomes all about the destination. It does, however, seem to be the right timing for both parties.
At the age of 27, Kane has been a faithful servant for the club, but with Spurs not able to win a trophy in all the years he has played for them, he can’t be blamed for wanting to move elsewhere, especially as there is no prospect of the UEFA Champions League next season.
Kane is a world-class striker and guarantees goals and there would be few top clubs who would not be interested if the price is right, though the price is going to be extremely high.
Just how high remains to be seen. This is going to be the first mega transfer of the COVID-19 world and it will be fascinating to see how it plays out and whether talk of £150 million ($273 million) is realistic.
With the player under contract for three more years, the ball is in Tottenham’s court but given Kane’s services and loyalty, you would think there would be an understanding that he wants to leave.
And, just like Kane is of an age where he has perhaps one mega move left in his career, the same is true for Spurs.
Regardless of whether it is wide in terms of team morale to keep your star player against his will, the longer he stays in north London, the more his value falls.
As the team look for a new manager, now is the time to cash in on their prized asset - even if it will be painful in the short-term for fans.
Selling Kane can bring in the kind of money that can be used to rebuild a team and buy two or three top-class players.
Spurs may even be able to negotiate with potential suitors to take a player or two as well as a hefty fee. If it is invested wisely then they can move to the next level.
The question is: where can he go?
If he wants to stay in England as is likely, and he is ‘only’ 96 goals away from breaking Alan Shearer’s Premier League goalscoring record, there are probably only three clubs that can afford him.
Chelsea could, and would be interested, but it is difficult to see Kane move across London to a club that is loathed by Spurs fans.
Kane is surely too loyal to do that and even if he did consider Stamford Bridge, it is hard to imagine chairman Daniel Levy sanctioning such a deal.
That leaves the two Manchester clubs. City are saying goodbye to Sergio Aguero and while they won the league in some comfort without a striker and prefer to buy younger players, it is said that Pep Guardiola came calling last year but Kane was persuaded to give Jose Mourinho another year.
The striker would surely win plenty of silverware there. That is less certain with Manchester United but the Red Devils are as desperate as Kane for the title and are a lot closer than Spurs.
While Kane is thought to prefer England, it would be understandable if Levy would prefer to sell overseas and not have the prospect of the player scoring against them every season and being on television screens and newspapers in England on a daily basis.
Paris Saint-Germain had the money for Lionel Messi and would have the money for Kane.
It makes sense for the club and would show Kylian Mbappe that PSG still have the ambition to be the best in Europe.
And linking up with former coach Mauricio Pochettino would be another plus-point for a player who was very close to the Argentine.
But getting Kane to France would be a challenge. The big two in Spain have, as we all know, serious financial issues and that doesn’t leave many options for Kane or Spurs.
It is in the interest of both that it is worked out. A chapter is about to close but the ending for both can be positive.