Sir Alex Ferguson has already warned Manchester United about the difficulties of dealing with Daniel Levy amid their Harry Kane interest.
Reports in the national media confirmed on Monday that the England captain wants to leave Tottenham Hotspur this summer.
MEN Sport understands he confided in Jose Mourinho on the day he was packing up his belongings that he intended on following him out of Spurs this year.
Manchester United have parked plans to sign a striker this summer, with a centre-back and midfielder a higher priority after Edinson Cavani penned a new deal last week.
Dimitar Berbatov was the last player to move from North London to Old Trafford in a deal that dragged across the entire summer. The Bulgarian eventually sealed a £30million transfer at the end of deadline day, such was Levy's persistence on the finer details of the deal.
Therefore, a move for Kane, Tottenham's undoubted star man, who has three years left on a six-year deal, will not come easy. Nor cheap.
The mooted fee of £150million would be a club record for United and a player who turns 28 in July.
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United had similar struggles with Tottenham when attempting to sign Michael Carrick in 2006, prompting Ferguson to outline the difficulties of negotiating with Levy.
"I must say negotiations were very difficult and went on for ages," said Ferguson of Carrick's £18.6million transfer.
"I always remember I thought it was done and [former Spurs chief executive] David Gill phoned me on the golf course to say they want more.
"Typical Daniel Levy! It was very hard to negotiate but, at the end of the day, we got it through and, ever since he joined us, he’s had a fantastic career."
After finally completing the Berbatov deal, he declared: "That whole experience was more painful than my hip replacement!"
