For a man who prides himself on deal-making in the transfer market, Daniel Levy is on the brink of making the biggest mistake of his life with Harry Kane.
Kane has been in the media in the last week talking about wanting a new deal at Spurs, which may seem surprising after a he signed a new five-and-a-half-year contract back in February worth £50,000-a-week.
I remember thinking about how strange that number seemed when Emmanuel Adebayor had spent years at Spurs doing nothing at all for £120,000 a week.
It proves to me that things have not changed in a hundred years and club owners will take advantage of any situation to turn a profit.
It doesn't take a genius to work out how crazy it is to risk a haggling match with Kane, a fantastic lad who wants to play for the club he supported as a boy more than he cares about money.
There's the problem. Levy took advantage of his love for the club last February when Kane signed a deal which paid way below the going rate for a 20-goal-a-season striker.
I don't think Kane had an agent at that point and for once, that was a bad thing, for the player and I believe Spurs too.
Levy now has to deal with a demand for more from a player who would fetch £60m plus on the transfer market, who is already coveted by all Mauricio Pochettino's Premier League rivals and is being tracked by the biggest clubs in Europe.
All of this while Pochettino struggles on with just one true striker, Kane, and a defence which looks as good as any at the top of the table.
That is not an insignificant thing. Pochettino had a big job to do during the summer to restore wounded pride after his players collapsed in the run in, took just two points from the last four games and blew the best chance they will ever have to win a title.
He bought Vincent Janssen as the hottest scoring property in Dutch football and so far, he hasn't shown much of the form which netted him 27 goals AZ Alkmaar last season.
All the more reason to make Kane the happiest player at Tottenham and give him a raise.
As I said, Pochettino had a job of management to do and evidence tells me that he has succeeded in getting one half of the equation working again which is his defence.
They don't let in many and I've already said more than once that such a quality could be absolutely crucial in this particular season. Spurs are tagged on at the back of the leading group but still in touch after drawing a lot of games.
The Champions League has been a chastening experience for them but I wouldn't be too worried about that.
You can't run before you can walk and what Pochettino's needs to do is consolidate in the top four and make sure he has another run at the Champions League next season.
Once he stays in touch with the top rank of teams, anything is possible because this will be a close race and any one of four or five teams could win it.
In fact, Levy need only look at what happens Spurs when Kane is not scoring goals to realise how vital he is.
It makes me laugh to think that Paul Pogba, who continues to underwhelm me at Old Trafford, is probably earning £50,000 a day and has had little or no impact on Manchester United's results since he arrived.
I watched them leak a goal in the dying moments against Arsenal and a range of pundits absolutely hammer Marcus Rashford for allowing Alex Oxlade-Chamberlain to get a run on him and cross for Olivier Giroud to score.
What they didn't mention was the fact that Pogba was loitering in midfield and made absolutely no attempt to track Oxlade-Chamberlain's run at a much earlier point in the play.
Graeme Souness was the only one to point out what was blindingly obvious to me but there is a kind of groupthink at work with Pogba.
Because he cost £84m and everyone was raving about how good he was last season in Serie A, people can't acknowledge that Pogba has been a dismal failure so far.
For me, if he is worth the salary they are paying him, Harry Kane should be getting £100,000-a-day and Levy is a fool if he decides to mess him around.