The Tottenham youth product has never publically or explicitly pushed for a move away but he has come close in the past, notably flirting with Manchester City two seasons ago prior to Erling Halland's (22) eventual arrival a year later. Now, however, a transfer feels closer than ever.
Manchester United, rejuvenated and competitive once more under Erik ten Hag (53), are being heavily linked with a summer move for him, with rumours circulating that Spurs chairman Daniel Levy may well budge on selling his club's star player this time around.
Reports suggest Levy is willing to let Kane go but only for an upfront £100m fee, and with United looking at prospective new ownership arriving in time for the start of next season, the fee and potential purchasing power of the Red Devils means a deal doesn't seem too far outside the realms of possibility.
Add to this Antonio Conte's (53) recent dramatic press conference meltdown all but signalling the end of yet another Tottenham manager's tenure during Kane's career, and it's easy to imagine the England captain is feeling like 'enough is enough'.
Not even a Mauricio Pochettino (51) return - something a majority of Spurs fans are demanding, and someone who enjoyed a fruitful working and personal relationship with Kane - would be enough to persuade him to stay, and nor should it.
Whoever comes in, be it Pochettino or anyone else, it's clear that the squad needs a drastic rebuild and decent clear-out - something it coincidentally desperately needed at the end of the Argentine's first stint - and with that comes the stark reality that the likelihood of Spurs competing for trophies in the next couple of seasons would be as slim as ever.
There's a very strong chance the club won't even qualify for the Champions League next term, with inconsistent form leading to a fourth-placed Tottenham suddenly nervously looking over their shoulders at the likes of Newcastle, Liverpool and even Brighton closing in with plenty of games in-hand.
While Pochettino garners plenty of plaudits for what he did during his time at Tottenham - taking them from fourth and fifth-place regulars to Premier League title challengers and the Champions League final, it is Kane who has actually been the vital cog in the machine, ever-present throughout the good times, and the one who has shouldered the burden to finally tip Tottenham over into a comparatively competitive status.
Spurs had been longing for a world-class talent such as his since the departures of Gareth Bale (33) and Luka Modric (37) years prior - and they struck gold with a relatively unfashionable striker from their youth academy who had been loaned out season after season with very mediocre results.
While ENIC, Joe Lewis and Levy will pat themselves on the back over a glistening new stadium, a fancy training ground and steadily profitable business models, it is Kane on the pitch who has led - or even, dragged - Tottenham to everything they've achieved within the last decade. Without him, they likely would have never had it so good, with no taste of the genuine big-time.
This is evidenced by the fact he became the club's all-time leading goalscorer earlier this year, overtaking legend Jimmy Greaves' 266 goals.
It would have been a shame to not see Kane break that record had he gone to City two summers ago. But now, after writing his name into Tottenham's history books and admirably sticking around to try and win something for his boyhood club, to hold him hostage if he wants to go in search of the trophies his career and legacy so richly deserve would be, frankly, nothing short of insulting to a club servant that has delivered everything within his power to provide.
With just a year left on his contract, Spurs won't want to risk losing their most valuable asset for free and will have to bite the bullet in letting him leave for a Premier League rival, particularly as he rightly hunts down Alan Shearer's (52) all-time goal-scoring record - something that is very much ripe for the picking.
It would no doubt hurt Spurs fans to see one of their all-time greats succeed elsewhere, but so long as it's not at Arsenal, they'll come to understand and ultimately get over losing their record goalscorer. Deep down, any genuine football fan knows it would be a travesty for Kane to go his entire career without a single trophy to his name.
If he wants to go he should be allowed to do so, knowing that he's been the integral, history-making piece in the puzzle that has propelled Tottenham to title scraps, a European Cup final, and ultimately everything that they are today in terms of size and stature. It's hard to ask any more from one player if you're unwilling to invest properly in the 10 others around him.