This article was first published in June 2020 and has been updated.

It felt like a secure long-term commitment when Harry Kane pledged his future at Tottenham in the summer of 2018, with the club on the brink of a new era of fortune and success.

Indeed, Spurs were a few weeks away from moving into their sanitary new stadium with a capacity of 62,000 seats, with Kane having scored 41 goals in 48 appearances for Mauricio Pochettino’s side in the previous term – the manager himself. – even had just signed a new five-year extension two weeks earlier.

As such, Kane felt compelled to put pen to paper for a big six-year contract who tied him to the club until the distant summer of 2024.

Fortunes have faltered since then, with Spurs parting ways with Pochettino, hiring Jose Mourinho, sacking Jose Mourinho and gradually seeing their once effervescent side competing for the title slowly breaking down and losing ground to their rivals.

After spending so many years as an almost-man at an almost-club, Kane now wants to leave Spurs in search of the trophies that have so far eluded him, sources telling ESPN that the reigning Premier Championships League Manchester City are extremely keen to provide this opportunity. .

However, the small matter of this six-year contract extension proves to be a big hurdle, with unwavering Spurs president Daniel Levy scrambling to prevent the desertion of his star man, who skipped training on Monday. and Tuesday in protest.

It remains to be seen how (and where) Kane emerges at the end of this rumbling saga, but it’s safe to say he’s not the first footballer to end up regretting signing too long a contract during the periods. party, and he almost certainly won’t be the last. Here is a selection.

Alan pardew

The last day of June 2020 was a really important day in Premier League circles as it marked the long-awaited expiration of Alan Pardew’s ridiculous eight-year contract with Newcastle United.

Pardew signed the gigantic extension in September 2012 after guiding Newcastle to European qualification the previous season, winning the manager of the season award. It was the longest contract for a manager working in the Premier League at the time.

It’s fair to say that the level of commitment shown by the club’s senior ranks has proven to be overzealous, with Pardew having left the ship midway through the 2013-14 season and returning to Crystal Palace apparently as soon as the post took office. vacant has been published.

Including Palace, Pardew took charge of no less than three other clubs in the time it took for his incredible contract at Newcastle to end. His last managerial term came at ADO Den Haag, which ended in 2020 after successfully avoiding relegation (largely due to the cancellation of the entire Eredivisie season due to the coronavirus pandemic) , while he is now technical director of the Bulgarian side of CSKA. Sofia.


Moyes David

Chosen by Sir Alex Ferguson as manager to succeed his dynasty at Manchester United, Moyes was ordained on a hefty six-year contract.

The rest, as they say, is a bit miserable and disappointing and ended prematurely just 10 months later.


Messi signed nine different contracts during his time at Barcelona (the photo below is from 2014), but the longest was the nine-year deal he made in September 2005, a few months after he made his entry into the first team.

Messi was hired until 2014 and doubled his salary in the process, but we think it’s safe to say that Barca definitely got more than their money’s worth as the Argentine quickly rose to greatness. .

Now that he’s 34, he still has long contracts, sources telling ESPN that a five-year contract to stay at Camp Nou awaits signing now that he’s a free agent this summer.


After becoming a staple of the tenacious Atletico Madrid midfielder, Saul put his pen to a huge nine-year contract in 2017 that would tie the 22-year-old to the club until 2026.

In a similar vein, midfielder partner Koke also had five years on his existing contract to tie him until 2024.

This bold move was taken partly to eliminate stakeholder interest (Manchester City are said to be spinning) and partly to cement Saul and Koke’s place at the heart of the squad for years to come. Although, like Kane, Saul may regret signing such a long contract, it is now reported that he wants to leave the club this summer.


Yet another La Liga star with a nine-year contract, Williams secured a massive deal with Athletic Bilbao in 2019 that could see the 26-year-old all-round striker playing his entire career at San Mames.

In other words, any interested club wishing to poach Williams from Bilbao will now have to shell out € 135million to trigger his new release clause.


A precursor to the mega-deals we see regularly today, Denilson became the most expensive player in the world when Real Betis paid him £ 21.5million in the aftermath of the 1998 World Cup.

The 20-year-old Brazilian winger signed a gigantic 10-year contract but ultimately struggled to keep his promises, failing to maintain consistent form and leaving La Liga for Bordeaux six years later (two of those moved to loan to Sao Paulo) with only seven years. goals in his name.


In thanks for his years of exemplary service, Barcelona presented Iniesta with a “lifetime contract” in October 2017 – a golden deal designed to keep the 33-year-old at Camp Nou for the rest of his career.

Six months later, he raised the sticks and moved to Japanese club Vissel Kobe, with Barca questioning whether they had wrongly assumed their contract was only symbolic.


Turan’s five-year contract with Barca ended last summer. He signed for Barca from Atletico Madrid in 2015 for € 34m, plus € 7m in add-ons. It was probably not good value for money.

It didn’t really seem like a fit at the time and it turned out to be, with Turan seeing his contract expire having not made a single appearance for the Catalan club since 2017.

The Turkey international was also unable to register and play for the first six months of his time at Barca due to a transfer ban. He is now in Galatasaray.


Fabregas signed an eight-year contract with Arsenal in 2006 as Arsene Wenger wanted to build his post-Invincibles squad around the young Spain midfielder.

Only 19 at the time, Fabregas gave the Gunners five good years before the magnetic pull of his DNA brought him back to Barcelona in 2011.


Thanks to a wave of cautious deals, City had a whole battalion of key players linked to the club in the long run.

De Bruyne was perhaps the most prominent name – among others Raheem Sterling, Ederson, Bernardo Silva, Phil Foden, Aymeric Laporte and Gabriel Jesus – the Belgian playmaker who agreed to a six-year extension in 2018. He has then recently signed a contract. new agreement in April until 2025.


Real Madrid were so keen on Casillas and Raul staying at the Bernabeu for the rest of their careers that they were both given “contracts for the rest of their sporting lives” in 2008.

The Casillas deal was a huge nine-year deal, while Raul (30 at the time) added a year to his existing contract.

However, both deals included a rollover clause that would automatically add an additional year to the contract if the player in question managed to make 30 appearances the previous season.

In all fairness, both players definitely spent their best years with Los Blancos, although both left the club long before the end of their respective ‘sporting lives’ – Casillas at FC Porto and Raul at Schalke – making the move a bit questionable. While President Florentino Perez’s comments about the pair have come to light, we may now know why.


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