His arrogance is crazy and makes him look pretty silly nowadays.
It was all very well 15 years ago when he was a top manager. He hasn't won a league title in 10 years or champions league in 15 years.
He is just another manager who couldn't move from 1 generation to the next when football moved on.
It's why Ancelotti is the best in my lifetime for me.
I'd actually say the exact opposite to that tbh.
While he was much more of a ticket shifter in the 00s than he is now, capable of selling out multiple nights at Knebworth back when it still had a huge capacity, the Glastonbury crowd of the time was much more of your NME reading "anyone that isn't Radiohead is sh*t" type affair. I think a much higher percentage of people (compared to now) would have turned their noses up at the big pop superstar and gone to something they perceived as "credible" instead.
Then in the 2010s both aspects lessened slightly - the Glastonbury crowd gradually became less pretentious, but RW wasn't shifting as many tickets so overall the "draw" of him at the festival broadly stayed the same.
I think it's only recently, where he's now seen as a more sympathetic figure and something of a self-aware national treasure, where the two could realistically meet. Even 10 years ago if they'd booked him there'd have been a lot of "That arrogant prick? No chance, I'm going to see the Chemical Brothers for the sixth time instead".
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