It was this time last year that Harry Kane was caught up in the midst of a transfer saga. Manchester City tried to sign the England captain in an audacious move that would have cost them $182 million. To cut a long story short, Kane felt he was entitled to leave after establishing a so-called 'gentleman’s agreement' with Tottenham Hotspur chairman Daniel Levy a season before Pep Guardiola came calling, but perhaps unsurprisingly, the 60-year-old businessman didn’t see it that way. 

Oh How The Tables Turned

Twelve months on from that 2021 summer of discontent when Kane temporarily went on strike and the 29-year-old is seemingly committed to the Spurs cause once more. If you bet on Premier League top goalscorer markets you will be aware of this change of heart from Kane. The forward is currently priced at odds of just 5/1 to claim the fourth Golden Boot of his career. 

In short, those odds indicate that Spurs are set to get the best out of their talisman forward and it’s hard to disagree with that verdict when you consider that Kane does appear to have been reenergized by Antonio Conte’s arrival. The Italian has, of course, worked wonders at the Tottenham Hotspur Stadium and even guided Spurs to Champions League qualification on the last day of the 2021/2022 season courtesy of a 5-0 win over Norwich. 

With this being the case, you can appreciate where Kane’s second wind has come from but simultaneously, it’s also worth asking how long the striker will remain content if Spurs go trophyless again in the upcoming campaign. After all, this is a man that is on course to become England’s leading goalscorer but astonishingly, has won no major honors domestically. It's a jarring reality for Kane to come to terms with.

Not only this but you imagine that the sense of urgency to make up for lost time will only amplify if Spurs fail to claim any silverware. Put another way, Kane’s head could quite easily turn once more should this limbo continue, and crucially, this time around, Spurs will have to listen to offers for his services as the 29-year-old’s contract expires in the summer of 2024. 

Harry Kane celebrates his 29th birthday today.

A goal Spurs fans will never get tired of watching 🎯

(via @SpursOfficial)pic.twitter.com/GFjsJ9dNW9

— B/R Football (@brfootball) July 28, 2022

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In this day and age, clubs rarely let a contract get down to the final 12 months without any sort of indication that a player is willing to stay. Essentially, this all leads to the 2022/2023 season being one of the most defining in Kane and Spurs’ history together. 

With this in mind, the question has to be whether it is now or never for both parties. In reality, the answer has to be yes with Kane committing 11 years of his career to Spurs without winning anything so far. There can be precious little room for sentimentality anymore and if the English forward is to extend his stay with the club, then Spurs are going to have to break their trophy drought and win something this season. It will either be boom or bust for Kane and Spurs with this longstanding saga approaching an enthralling end.

Bayern director Oliver Kahn on Harry Kane after denying Cristiano Ronaldo deal: "I can just say that Harry Kane is an outstanding striker who is now under contract at Tottenham", told Bild 🔴 #FCBayern

Again, Tottenham consider Kane untouchable. It's not even a topic this year. pic.twitter.com/Ag0iRsNDKI

— Fabrizio Romano (@FabrizioRomano) July 27, 2022