Harry Kane's loyalty is respectable but it's never been more obvious that he has to leave Tottenham Hotspur

As the final whistle blew at the Tottenham Hotspur Stadium on Wednesday night my first thought was that yet again a chance for Harry Kane to win a trophy had disappeared.

Don't get me wrong, I wasn't expecting Spurs to lift the Champions League this season, I'm not that deluded a human, but bad teams have been successful in Europe before.

They had already crashed out of the Carabao Cup to Nottingham Forest back in November and just over a week ago they lost in the FA Cup to Championship Sheffield United.

Kane didn't start that game but you could see his reaction when his late header went wide that yet another chance of winning a trophy had gone.

Every single time they have been knocked out of a competition this season it has been in the limpest possible fashion, as Wednesday proved.

Conte seemed to be trying to get himself sacked in his post match interview and fans chanted for the return of Mauricio Pochettino.

For Kane though, it really should be the beginning of the end. He can stay, and try to recreate the magic with Poch, but it would be a huge error.

At 29-years-old, 30 by the start of next season, he is by no means nearing the end of his career but he is starting to risk going the entire time without winning silverware.

There's no doubt that he will go down as a Premier League great goalscorer, there's every chance he will overtake Alan Shearer's record, that has seemed untouchable at times, but how important will those goals ever be.

I'm not saying a Carabao Cup win would suddenly make all the difference to how good the England captain is, or will be seen as when he hangs up his boots, but there's no doubt there will be questions.

Should the striker end his career with no medals won then he would surely be the greatest player to never win a single thing, it's difficult to think of anyone who comes close.

Kane after missing a chance against Sheffield United. Image: Alamy

Steven Gerrard is often criticised by his detractors, mainly those who want to argue for Paul Scholes or Frank Lampard, for not winning the league.

The Liverpool legend still won the Champions League, two FA Cups, three League Cups, as well as the Community Shield, UEFA Cup and Super Cup.

Shearer himself only won the league, but he won the league, his goals undoubtedly mattered to Blackburn Rovers success, as they overhauled a Manchester United team who were dominant.

At this moment in time Kane's goals are only to get Spurs into the top four, and whilst they're in that position right now, even that looks like a slim chance with Liverpool's resurgence.

Of course, Kane has been in this position before, Manchester City wanted him in the summer of 2021 but Tottenham wouldn't budge on the price.

Then the forward had four years to run and with no official clause in his contract, just a gentleman's agreement between Daniel Levy and Kane's brother/agent Charlie, there was little chance of the north London side bending to their huge asking price.

Daniel Levy won't want Kane to go for cheap, even with their only. being one year left on the star's contract. Image: Alamy

Now he has only two years left on his contract and Manchester United are desperate for a striker this summer, it might be the place for him to go.

Of course not everything is perfect at Old Trafford, see Sunday's loss to Liverpool, but they are back on the trophy winning trail after the Carabao success.

With Kane upfront they would be genuine title contenders once again, and certainly their chances of more silverware would be strengthened.

Erik ten Hag has proved how important winning competitions is to him, remaining in all four, whereas, should he return to Spurs, Pochettino doesn't have that mindset.

During his time at Spurs, the Argentine said, "Again we're going to have the debate whether a trophy will take the club to the next level. I don't agree with it. It only builds your ego."

Kane may have had a great bond with Pochettino but he can't let that get in the way of his decision to stay, if the former manager returns. Image: Alamy

In some ways he had a point, what he did with the team was about more than trophies, taking them to new levels, and a Carabao or FA Cup win might not have saved him, but with a trophy teams have something to point at, to hold, to show their development.

Trophies matter, they might not be the only thing that do, but it's impossible not to think that Kane won't be questioned if he never wins anything.

Now is the perfect time to leave Spurs, he has done so much for them already, he owes them nothing, as much as you can respect his loyalty to this point, they've not done enough to award him for that.