Recall Villas-Boas was in charge of Tottenham in 2012/13 session and gave Kane his Premier League bow but disagreed with the youngster over how he could best develop, with the player unwilling to leave on loan at the start of the 2013-14 term.
It was after Villas-Boas departed in December of that campaign when Kane truly came to the fore and following four seasons of 30-plus goals for club and country, the 24-year-old has constantly found himself linked with Real Madrid.
And though Kane has an emotional attachment to his boyhood club, Villas-Boas has told Press Association Sport that such a factor could be outweighed by the wish to claim multiple winners’ medals elsewhere.
“It depends on Harry and his ambitions for the future and how he sees his career going forward,”said the Portuguese, who was speaking in Monaco as an ambassador for Laureus.
“If he has a hunger for trophies and for notoriety he would have to leave Spurs, if he has no hunger for that, but (wants) recognition and stability, he would stay at Spurs.
“Spurs are in that breakout moment of becoming a great football team – the (new) stadium, infrastructure, training ground is there, the team is building up, very well managed.
“The trophy cabinet is still what is missing for this great club. That is in the end what footballers chase – glory, winning.
“I think for Harry, one or two more years at Spurs wouldn’t be bad and then see how the club develops. With the new stadium coming through I also think that Spurs should have that margin from him.”