Crespo is a huge Kane fan but thinks he needs to leave White Hart Lane to mark his rising career with silverware.
The Argentine acknowledges a switch would be “difficult” due to the close rivalry between the London giants.
But speaking exclusively to the Express, Crespo has pondered the possibility of the England star moving to Stamford Bridge.
Speaking to the Express in his role as a Betstars ambassador, Crespo said: “Harry Kane is a great striker but he's just like Tottenham.
“You need to win. If you win you are a great striker, you need to win. He's demonstrated he's very important.
“It's like Alan Shearer - a big striker but with Blackburn, bang, he won. After that, boom, national team, big. If you win, you're another level.
“Kane needs to help the team win trophies and to do it with Tottenham would be great.
“He tried to do it last year and didn’t. If it doesn't happen, Harry Kane must change. He must.
“He must move to win, to a big team, to Chelsea, although Chelsea would be difficult.
“Maybe Manchester City, why not? Manchester United after signing Romelu Lukaku would be difficult.
“Next season, everything could change with Kane.”
Hernan Crespo has made the Big Call with online betting site BetStars. He is backing Manchester United to win the Premier League. #CallIt at www.betstars.uk/sites/football/crespo/
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