The forward is eager to win trophies - but that looks unlikely to happen under Thomas Tuchel this season
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As Bayern Munich continue their hunt for a replacement for Thomas Tuchel, Harry Kane can be forgiven for feeling worried.
This is a huge moment in the England international's career. He thought trophies would follow when he ditched Tottenham for the Bundesliga back in the summer but, as things stand, he looks poised to go without.
Bayern won't be winning the league, with Bayer Leverkusen superior in every department and still unbeaten under Xabi Alonso.
They lost to RB Leipzig in the Super Cup and sensationally exited the DFB-Pokal at the hands of minnows Saarbruecken back in November.
Harry Kane's future is set to be shaped by Bayern Munich and their decision on who replaces Thomas Tuchel
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And while they remain in the hunt for Champions League glory, Arsenal will pose a tough test. One that this Bayern side may not be able to overcome.
Tuchel signed Kane back in the summer but the German will be departing at the end of the season, with all parties agreeing enough is enough.
And Bayern are currently probing the market as they hunt for a replacement, with several managers being linked.
Julian Nagelsmann has been touted for a sensational return, with the Germany boss unfairly sacked by Bayern in March last year.
Roberto De Zerbi is admired, having worked wonders at Brighton, while former boss Hansi Flick - who guided the club to a terrific treble triumph in 2020 - is on the market.
There's also Ralf Rangnick who, his dreadful spell at Manchester United aside, has a reputation for improving managers.
As for Kane will be turning 31 in July. He is now in the peak years of his career, with the twilight years lying ahead.
If he's to finally win a trophy, then Bayern need to get their next appointment right.
Whoever it is, Kane will continue to score goals. He always has, no matter the circumstances or the man in the dugout.
But this summer will put the England international at a crossroads. There's a genuine sense of now or never.
Kane has played under serial winners such as Tuchel, Antonio Conte and Jose Mourinho throughout his career with no trophies to show for it.
Even Mauricio Pochettino, previously beloved in north London, couldn't end the club's wait for a first piece of silverware since 2008.
Of the candidates to take over from Tuchel, there's no standout one. Each and every name on the list carries an element of risk.
Nagelsmann did well enough first time around but still didn't keep the Bayern board happy, while also clashing with several high-profile first-team players.
Robert Lewandowski would, perhaps, still be a Bayern player now if Nagelsmann hadn't ruled the roost at the time of his departure to Barcelona in the summer of 2022.
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Harry Kane has played under serial winners such as Jose Mourinho and Antonio Conte without winning a trophy
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De Zerbi has obviously improved Brighton, continuing the work that was started by predecessor Graham Potter.
Yet managing at the Allianz Arena is drastically different to the Amex Stadium and the leap could yet be too big for him to make.
Flick was a huge success during his first stint at Bayern.
However, his reputation has suffered a huge blow following his dire stint in charge of the Germany national team.
And Rangnick's issues at United mean he's hardly first-choice in the eyes of Bayern fans to take over from Tuchel at the end of the season.
Harry Kane deserves to win trophies as Bayern Munich continue their hunt for a Thomas Tuchel replacement
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Kane deserves to win a trophy.
Yet if Bayern don't get their next managerial appointment right, then it's possible it will never happen.
Leverkusen are, after all, poised to build on the brilliant work Alonso has already done.
What ultimately happens remains to be seen.