Former Tottenham striker Jurgen Klinsmann says Harry Kane's sale will spark a player exodus.
The club's ageing squad is likely to need an overhaul - a task that may only be made more difficult were Kane to seek pastures new.
Klinsmann believes showdown talks will be on the agenda but has warned Tottenham that selling Kane could have huge knock-on affects.
He told Sky Sports: "I feel sympathy for both sides, especially Harry, who has been the flag of the club for so many years. He's done so much for them.
"The market is out there for him. Teams would grab him right away and they'd probably put down a lot of money.
"I personally hope he stays at Spurs but I also can understand him. I was in that situation in 1995. I badly wanted silverware and it worked out that way.
"I went to Bayern Munch and won the UEFA Cup and German championship.
"If Harry leaves then you have a problem because maybe [Heung-Min] Son says: 'Hang on, I might move on as well then'.
"The most important path now is [for Spurs] to sit down with Harry, discuss the situation and lay out how he can continue his career with Spurs, how the roster will look for next season to make the squad even stronger.
"The quality is there. It needs a bit of fixing up but the key figure in all this is definitely Harry Kane. You've got to do everything possible to keep him."