If anyone knows how tough it is to force an exit from Tottenham it is former Manchester United striker Dimitar Berbatov.
Harry Kane's future at the London club is uncertain as he looks to push through a summer move to reigning champions Manchester City.
Berbatov found himself in a similar place back in 2008 before he eventually completed a £30.75m move to join the Red Devils.
The Bulgarian striker has revealed that dealing with chairman Daniel Levy and trying to push through a move to play for Sir Alex Ferguson at Old Trafford was 'mentally exhausting'.
When asked about Kane's potential departure, he told Betfair: "I expect it will be left until the last possible moment. Having been through that in 2008, I don't want it to be that way and I would like it if the deal to happen as soon as possible.
"On deadline day 2008, I was still in London and my agent went to meet Levy. I was so mentally exhausted from everything going on that I needed to sleep in the afternoon from all the emotion.
"Whilst I was taking a nap I dreamt I flew to Manchester then made my debut for United. I woke up with my agent calling. He said: 'Wake up and get ready, we're going on a plane to Manchester.'
"We got on the plane, I signed the contract with minutes to spare before the deadline and the rest is history."
Berbatov had been linked with United for the majority of that summer after scoring 23 goals in 52 appearances with Spurs in the 2007-08 season.
Unlike Kane, as the Bulgarian looked to force through a move he didn't fail to show up in training - but he did in fact miss two games for Spurs.
The 40 year old said: "I missed two games for Spurs when my transfer to United was about to happen and, looking back, I don't think it played much of a role in getting my move. I didn't skip training but I showed that I wanted to leave.
"It was an unfortunate situation and it was tearing me apart inside because I'm not the type of person who wants to do that.
"When it comes to this moment, you need to be tough, unfortunately, and in business, you need to be tough and stand your ground. The person who is the most affected when you do this is the player.
"Physically and mentally, it gets you down. You think about all scenarios and you get mentally exhausted. Even though I did it, one of the worst things that could happen would be for Kane to boycott Spurs matches.
"That would be painful to watch and difficult to swallow for the fans and everybody connected with the club. I don't want to see that happening. It would put even more fuel on the fire."
