Former Tottenham striker Dimitar Berbatov says Harry Kane must decide when it is time to leave for a "big club".
The future of the England captain is a big talking point during football's lockdown, with Manchester United keen admirers.
Kane is expected to fetch a fee close to the world-record sum Paris Saint-Germain paid for Neymar in 2017, though Standard Sport understands Spurs would not consider a sale.
Berbatov made the switch from north London to Old Trafford in 2008, going on to win the Premier League twice and League Cup once.
And Berbatov says, as Tottenham's trophy drought stretches to 12 years, Kane must decide if he needs to leave Spurs to win silverware.
"The sad thing in football is that, because it has been established a long time ago which the big clubs are, you will always have that situation with teams like Spurs where their best players have to decide if they stay here or move to a big club," he told BBC.
"It is exactly the same with Harry Kane at the moment. He is going to be at a crossroad, thinking 'what do I do now?'.
"The situation is maybe difficult now because of coronavirus and the money, but he is in exactly the same situation I was in. In his head sometimes he is maybe not in the right place.
"My head was not in the right place at times. How can it be? I don't want to put my team in a position where I go late in the window and leave them without a replacement. But it will happen after me many times, with many players.
"The most painful part is that Spurs' last trophy was when me and Jermaine where there. It will be stated over and over again and make people angry that the lack of trophies is the main problem for players like Kane, who is captain of England and not getting younger.
"But when he gets older he wants to say to his kids: 'Look what I won'."
