Harry Kane aggrieved at Tottenham’s transfer stance but ‘gentleman’s agreements’ rarely benefit the player

Whenever the term “gentleman’s agreement” is mentioned in football there is a strong possibility that a player is being shafted. And that all the sympathy will go to the club. Harry Kane will recognise the scenario.

The Tottenham Hotspur striker’s image has taken a beating this week. The 28-year-old did not turn up for pre-season training on Monday because the club will not sanction a transfer to Manchester City. Kane believes that he had an arrangement with Daniel Levy, the chairman, that would allow him to leave in the right set of circumstances. The striker maintains the conditions have been met. Spurs deny any agreement exists.

Levy has previous for this – at least according to Luka Modic. The Croat signed a contract in 2010 and it was informally agreed that if a “bigger” club came in that Modric could leave. A year on, Levy ignored a bid from Chelsea and the midfielder was forced to remain at White Hart Lane for another season. The next summer Modric had learnt his lesson. He refused to go on a pre-season tour of the United States and got his move to Real Madrid.

The questions that are being asked of Kane are simple: why did he sign a six-year contract in 2018 and why should he break that deal? The first answer is obvious. The extension doubled his salary to £200,000 a week. But there were benefits for Tottenham, too.

The long-term contract protected Kane’s value in the transfer market. Most players are happy to do this: both sides win in this situation. Had the England captain not extended three years ago, he would have been a free agent next summer. He could have begun to negotiate with other clubs in the new year and leave after the coming campaign without Tottenham recouping a penny. Long contracts give clubs extra protection and it is fairly common for them to tell a player that they will not stand in their way if a suitable offer arrives and the team cannot meet his ambition. None of this is written down.

Kane obviously wants to play in the Champions League. Tottenham are in the Europa Conference League qualifying play-offs. There are few clearer cases of a player outpacing a club.

Kane’s absence from training suggests that there is little chance of rapprochement. It is now all about negotiating the right price. A simplistic analysis is that Levy has all the power. He does not need to sanction the transfer unless he gets the fee he wants.

The situation is much more complex. The Spurs chairman has a reputation for being a tough negotiator. Often, Levy has waited while the minutes ticked down to the end of the transfer window and watched potential buyers become more and more desperate. This ploy may not be as successful in the second summer of Covid, especially when dealing with City.

The champions are one of the few clubs with money to spend. They are on the verge of paying £100 million to Aston Villa for Jack Grealish. They can afford to splash out for Kane but they know that Tottenham are short of cash and need to rebuild a team that finished seventh in the Premier League in May.

Levy’s ability to come out on the positive end of a transaction has relied on a relatively straightforward stance – that Tottenham don’t need to sell. In this case, City don’t need to buy, at least not from Spurs. If they dropped their interest in Kane, Levy would be left with a dissatisfied talisman and a squad that is not good enough to compete for the top four. There are no other buyers out there.

The Tottenham chairman’s towering achievement was to build the new stadium but the pandemic has turned this into a financial deadweight – at least in the short term. There is no money to rebuild the team without Kane’s sale. The striker’s value will never be higher but there is little point in maximising it by waiting until August 31 if Spurs cannot bring players in with the profits.

It is easy to see Levy’s point of view. In a transfer market where Ben White is worth £50 million, Kane must be valued at significantly more than £160 million. Yet the 59-year-old may have overplayed his hand. His captain has been a model professional and has shown his loyalty to Tottenham on numerous occasions. Kane is convinced he has been mistreated. There is no going back.

City are used to bullying other clubs with money. They will not be bullied. The battles with Uefa that ended up in the Court of Arbitration for Sport – as well as the bottomless pit of money from Abu Dhabi – have changed the mindset at the Etihad. The English champions are almost at the point of becoming the Bond villains of world football, acting with a swagger and arrogance that outstrips even the traditional big beasts of Barcelona and Real. City could pay the asking price without the slightest worry but if Levy irritates them they could teach him a lesson.

Kane is in the middle. He lost the PR war when he boycotted training. He will be labelled greedy, despite being consistently underpaid – by world-class footballing standards – throughout his time at White Hart Lane. That situation probably would have continued if Spurs had been able to win silverware. Two things keep superstars at clubs: going-rate money and medals. Tottenham offer neither.

Things are already turning ugly. Invariably, only one side benefits from a “gentleman’s agreement” and it’s rarely the player.