The Chelsea owner is reportedly preparing a £60million bid which is likely to insult the Tottenham hierarchy, writes the Express.
Kane has expressed his desire to leave the north London club in search of silverware this summer, but Spurs are expected to only think about considering bids in excess of £150million for their star player.
And London rivals Chelsea, who have a fractious transfer history with Tottenham, are risking enraging their nearby neighbours with an insultingly low bid of £60m for the Premier League top-scorer and England captain.
That is what they are preparing to offer according to a report by transfer expert Gianluca di Marzio.
Chelsea famously tried to tempt then Tottenham midfielder Luka Modric across London in 2011, upsetting the Spurs board to such an extent that Levy vetoed any future move. The Croatian subsequently joined Real Madrid the following summer.
And Chelsea also hijacked a Spurs deal for wide man Willian in 2013, gazumping Tottenham at the eleventh-hour when the Brazilian was already in town for a medical.
Such is the bad blood between the two clubs, it was always unlikely that Spurs would be open to selling Kane to Chelsea.
But if such an insultingly low bid were to be made then Levy would almost certainly veto a transfer once again.
A £60m Chelsea bid would be closer to England striker Kane’s valuation of himself at £100m than to Tottenham’s minimum of £150m.
“I mean he [Daniel Levy] might want to sell me,” Kane told pundit Gary Neville last month. “He might be thinking ‘If I could get £100m for you, then why not?’… do you know what I mean? I’m not going to be worth that for the next two or three years.
“I want to play the Champions League… I want to be playing in the biggest games. I’ve said before, I’d never say that I’d stay at Spurs for the rest of my career. I’d never say that I would leave Spurs.”
A Chelsea approach for Kane would be made even more complicated by the impending arrival of a new sporting director at Tottenham.
Fabio Paratici, who parted ways with Juventus earlier this summer, is expected to join the club this week as a sporting director, taking over transfer operations from chairman Levy.
And Paratici’s first brief will be to do all he can to keep Kane. If all else fails, the Italian will want a huge transfer kitty from a Kane sale with which to reshape the squad.
And £60m certainly won’t be deemed enough by Levy and co.
Any decision over Kane’s future is unlikely to be made before July, with the 27-year-old currently focused on leading England’s campaign at the Euro 2020.
Kane and his international team-mates get their campaign underway on Sunday afternoon against Croatia, with further matches against Scotland and the Czech Republic to follow in Group D.