In his contract, he has an option to buy a franchise of an expansion team in the MLS. It suggested he might get a New York franchise. He is integral to the league there and totally locked in with Anschutz and AEG. MLS franchises are becoming licenses to print money.
At best, his alternative would have been an additional 18 months pissing around on the bench at Milan or Tottenham "proving himself at the top level".
Some mistake. I'd like to be making mistakes like that.
I don't disagree that he did well personally out of the move. My point was that, from a footballing perspective, he shot himself in the foot, so to speak. He couldn't prove he still had the ability to cut it at the highest level in the MLS, hence the debate over his abilities. If, as you infer, he ended up on the bench at Tottenham, it would have proved that his days at the top were over. If he went there and took Tottenham to the Champions League, he would have answered his critics. By going across the Atlantic, he lost the chance to prove himself after serious doubts had been cast.
Furthermore, going on what he has since done with the moves to Milan and the commitment to England, I think he has pretty much admitted through his actions that this move was a mistake for his football career.