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          Kane's Tottenham regret? Ranking the longest contracts ever signed, including Moyes, Messi, Iniesta

          • Chris Wright, Toe Poke writerAug 3, 2021, 07:00 AM ET

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

          It looked like an assured long-term commitment when Harry Kane pledged his future to Tottenham back in the summer of 2018, with the club poised on the brink of a brave new era of fortune and success.

          Indeed, Spurs were weeks away from moving into their salubrious new 62,000-capacity stadium with Kane having scored 41 goals in 48 appearances for Mauricio Pochettino's side the previous term -- the manager himself having just signed a new five-year extension two weeks prior.

          As such, Kane felt compelled to put pen to paper on a hefty six-year deal which tied him to the club until the distant summer of 2024.

          Fortunes have wavered since then, with Spurs parting company with Pochettino, hiring Jose Mourinho, firing Jose Mourinho and gradually seeing their once-effervescent title-challenging side slowly break apart and lose ground on their rivals.

          After spending so many years as a nearly man at a nearly club, Kane is now keen to leave Spurs in search of the trophies that have thus far eluded him, with sources telling ESPN that reigning Premier League champions Manchester City extremely keen to provide that opportunity.

          However, the small matter of that six-year contract extension is proving a sizeable barrier, with Spurs' unshakeable chairman Daniel Levy digging his heels in hard to prevent the desertion of his star man, who skipped training on Monday and Tuesday in protest.

          It remains to be seen just how (and where) Kane emerges at the conclusion of this rumbling saga, but it's safe to say he's not the first footballer to eventually come to regret signing an overly-lengthy contract during times of feast, and he almost certainly won't be the last. Here's a selection.

          Alan Pardew

          The final day of June 2020 was a truly momentous 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 mammoth extension in September 2012 having guided Newcastle to European qualification the season prior, winning the Manager of the Season award as a result. It was the longest deal for any manager working in the Premier League at that time.

          It's fair to say that the level of commitment shown by the club's top brass proved to be over-zealous, with Pardew jumping ship halfway through the 2013-14 season and returning to Crystal Palace seemingly no sooner than the vacancy been posted.

          Including Palace, Pardew has taken charge of no less than three other clubs in the time it's taken for his incredible Newcastle contract to run out. His most recent managerial tenure came at ADO Den Haag, which came to an end in 2020 after successfully avoiding relegation (largely by virtue of the entire Eredivisie season being cancelled due to the coronavirus pandemic), while he is now technical director at Bulgarian side CSKA Sofia.

          RANK: BIG MISS

          David Moyes

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

          The rest, as they say, is all slightly unfortunate and underwhelming and came to a premature end just 10 months later.

          RANK: BIG MISS

          Lionel Messi

          Messi has signed nine different contracts during his time at Barcelona (the picture below is from 2014) but the longest was the nine-year deal he agreed in September 2005, a matter of months after breaking through into the first team.

          Messi was signed up until 2014 and doubled his wages 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 ascended to greatness.

          Now he's 34, he's still getting long deals, with sources telling ESPN that a five-year contract to stay at Camp Nou awaits his signature now he's a free agent this summer.

          RANK: HIT

          Saul Niguez (and Koke)

          After becoming a staple of Atletico Madrid's tenacious midfield, Saul put pen to paper on a huge nine-year contract in 2017 that would tie the then 22-year-old to the club until 2026.

          In much the same vein, midfield partner Koke also had five years tacked onto his existing deal to tie him down until 2024.

          The bold move was partly made to nix interest from interested parties (Manchester City were reported to be circling) and partly to cement Saul and Koke's place at the heart of the team for years to come. Though, like Kane, Saul may come to regret signing such a long deal now it's reported he wants to leave the club this summer.

          RANK: HIT

          Inaki Williams

          Yet another La Liga star foisted with a nine-year deal, Williams agreed a vast contract with Athletic Bilbao in 2019 that could see the versatile 26-year-old forward play out his entire career at San Mames.

          Put it this way, any interested club wishing to poach Williams from Bilbao will now have to stump up a cool €135m to trigger his new release clause.

          RANK: HIT

          Denilson

          A precursor to the mega deals we regularly witness today, Denilson became the most expensive player in the world when Real Betis forked out £21.5m for him in the aftermath of the 1998 World Cup.

          The 20-year-old Brazilian winger agreed a gigantic 10-year contract but ultimately struggled to deliver, failing to maintain any consistent form and leaving La Liga for Bordeaux six years later (two of those spent on loan at Sao Paulo) with just seven goals to his name.

          RANK: MISS

          Andres Iniesta

          In gratitude 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 the Camp Nou for the rest of his career.

          Six months later, he upped sticks and moved to Japanese club Vissel Kobe with Barca left wondering if he'd mistakenly assumed their contract was merely symbolic.

          RANK: MISS

          Arda Turan

          Turan's five-year contract at Barca came to an end last summer. He signed for Barca from Atletico Madrid in 2015 for €34m, plus €7m in add-ons. It probably wasn't value for money.

          It didn't really seem like a good fit at the time and so it proved to be, with Turan seeing his deal 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 Barca stint due to a transfer ban. He's now at Galatasaray.

          RANK: BIG MISS

          Cesc Fabregas

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

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

          RANK: HIT

          Kevin De Bruyne

          Thanks to a wave of prudent deals, City had an entire battalion of key players tied to the club long-term.

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

          RANK: HIT

          Iker Casillas and Raul

          Real Madrid were so keen for Casillas and Raul to remain at the Bernabeu for the rest of their careers that the pair were both handed "contracts for the rest of their sporting lives" in 2008.

          Casillas' deal was an enormous nine-year agreement, while Raul (aged 30 at the time) added one year to his existing contract.

          However, both deals included a rolling clause that would automatically add an extra year to the contract should the player in question manage to make 30 appearances the season before.

          In fairness, both players definitely spent their best years with Los Blancos, though both left the club well before the end of their respective "sporting lives" -- Casillas to FC Porto and Raul to Schalke -- rendering the whole gesture a bit moot. Though now president Florentino Perez's comments about the pair have come to light, perhaps now we know why.

          RANK: MISS