I know most people's answer to this question is, yes. But, taking aside fans' romanticism, overtly rose glasses and the "fact" that Manchester United, the team Kane is most linked to, would "conquer the world" with Kane, I think everyone would find the story to be more complicated than just titles. And maybe, just maybe, if you bear with me until the end, you'd actually see that Kane staying at Spurs might actually be the best decision for Kane.

Reasons to stay

There's a fact that will come up more than a few times in this article that I didn't mention in the last part, so let's open with it. I was saving this fact for this post, but @talesfrmthecrypt phrased it much better and right to the point and I believe there are a few better people to double this claim:

I certainly think that this season he isn’t dropping as deep and linking play and that in turn is one of the reasons that Son has struggled while Kane has been more consistent as a goal scorer

Kane has become "more consistent as a goal scorer", and that's a fact. We already know Kane had that finishing sense for many years. However, the fact that Kane is being relied upon more as a finisher doesn't only matter in his staying in Spurs, but also when it comes when discussing his options, but more on that later.

So, Kane is now Spurs' main source of goals and that's great for him because he is a man chasing a difficult record of 260 goals in total, so it's better to just stay put if that's the target. But, also the fact, why wouldn't choose to be a club's loyal legend, the untouchable that will always have fans wishing they had in their team?

Think about it for a second, would Francesco Totti be as memorable if his only league title was won with Juventus, or Real Madrid, with whom he was heavily linked and almost moved? Would Steven Gerard be an undisputed legend of the game if he had moved to Chelsea when Mourinho requested him? Many legends come to mind who never won many or even any titles are regarded as legends because we know they could have chosen any club and would have won more titles there.

I know people would mention that Kane himself wanted to move to Manchester City last season, and assuming that's a fact. We also need to remember that all loyal legends had that moment of doubt, that moment when a move to another club looked better. Legends were always tempted to leave, in fact, I'd be Alan Shearer himself
often regrets not moving to Manchester United. Legends always had, it was just temporary.

There are always ways to force a move out of a club, in fact, Spurs had that a few years back when Real Madrid signed Gareth Bale as the Welsh stopped showing up to training to force the move. Kane could have done the same, and I doubt many Spurs fans would blame him or hate him for it. Kane didn't do any of that.

This adds to the fact that he is now Spurs' most beloved player, a legend certainly, and the captain of the national team. He recently became Spurs' top scorer of all time and would be looking to extend his record further and further.

The funny part about Kane and all the other legends we mentioned is that he is not treated as a loyal player, but rather as a player who "wasted his career at Spurs". But, along the same line, would Kane's goals matter as much if they were scored at Manchester City? How much would you even care about Kane's presence at Manchester City if he had joined the club and won his Premier League trophy with them?

Not to sound like Wenger with the "4th place is a trophy", but everything Kane reached with Spurs is an accomplishment. From being consistently in the UEFA Champions League, reaching its final, and beating teams like Manchester United, Manchester City, Liverpool, Chelsea, and Arsenal. You could always look at those accomplishments and think of Kane as a main reason. A simple reverse with City could also show that if we say it was Manchester City who beat Spurs last game with a Kane goal.

We could say that Spurs couldn't beat Manchester City without Kane, but even if Manchester City beat Spurs 1-0 with a Kane goal, we wouldn't be credited as much as we could easily say, "someone else would have scored anyway". And that's the value of Kane's presence at Spurs, his goal record is an accomplishment that is much more appreciated. In fact, they are the reason you always say that he "wasted his career at Spurs". The funny issue is, if his record was achieved at Manchester City, most people won't even care.

Are there really better options?

Let's evaluate Kane's options. First, with Haaland at Manchester City, that's definitely not a real option. Liverpool spent 70 million on Darwin Núñez, so that's not an option really. I know Manchester United and Arsenal fans consider their teams "much ahead" of Spurs, but that's just not true even though it is easy to look at the league position and laugh at my statement. But, once the new season starts, all the top 6 clubs, with the exception of Manchester City, would have about the same odds of winning the league making any move there a sideways move.

This means that the league title odds are the same and are the local cups really worth transferring for.

Keeping in mind that Manchester United under Ten Hag would be focused on Rashford as a goal scorer mainly, and remember Kane is currently the finisher at Spurs, this means that Kane would be actually harming his odds of beating Alan Shearer's record.

You might argue that Manchester United could switch to Kane as their finisher, which is doubtful because why would the club shift focus from a player in his mid-20 to a player who'd be 30 years old by the time he gets there? But, even if true they'd be put equal to Spurs where Kane is much more beloved by fans and his goals are celebrated more.

Outside of England, Real Madrid is the only option as Kane's transfer fee won't be little. The Spanish side, however, is still focused on Mbappe plus their project is more focused on younger players anyway. Plus, this would actually definitely kill Kane's chances of equalizing Alan Shearer's record, and with Real Madrid's old guards nearing retirement age, Real Madrid has a few hard years ahead, so even then titles won't be guaranteed with Barcelona in the same country.

In Conclusion

To be honest, all of this debate doesn't really matter in the practical world. It just exists because people love picking on and mocking clubs that don't have a full trophy cabinet, as if that isn't 95% of the clubs around the world. It also points to a bipolar way of thinking where people want more competitive teams yet also want to strip smaller teams of the stars that would allow them to compete. But, more on that in the final part.

The main reason it doesn't matter actually has to do with Harry Kane himself. Is he happy staying at Spurs? The way I see it, he is. If he wasn't and decides to leave, then so be it. This is Kane's career after all, no one has any right to blame or hate him for it. No player had a career without regret here or there. Whatever Kane decides to do is actually the right decision as he is the only one who gets to reap his career at the end with all its accomplishments, missed opportunities, regret, and celebration.