He can't win either, he lacks ambition or gets mocked for sticking it out with Spurs and not winning a trophy. Gets mocked for winning an easy trophies with Bayern.
Footballing-wise Bayern is the perfect transfer for him tbh, he fits their team really well, will bring their wide forwards into play, score lots. They'll be a force in the CL.
And it's generally senseless because winning trophies with Chelsea, City, United or Liverpool isn't exactly difficult, even in our worst times we managed to get trophies when we managed to be competent for a short period of time. All his options are top clubs and they all win trophies relatively regularly without him or someone of his caliber upfront. The entire thing is senseless.