Thanks for the thoughtful input, ManoBear
For me, the problem with Donovan is that he's choose to be a big fish in a small pond and has never really given tried to make his mark in a big league. His stint in the Bundesliga was brief and unsuccessful, and his little stints at Everton have been tantalizing, but that's it. Although I think Donovan's the best American player (besides Jon O'Brien) to ever touch the ball, we'll never know how good he really could have been because of his refusal to compete week in, week out at a top level league. And I think that's a loss for him and US football, because he's the one player who (IMO) could have walked onto a big five team in the EPL and made a mark.
So for me it's hats off to Clint Dempsey, Claudio Reyna, John Harkes, Carlos Bocanegra and Brian McBride (who's rightly worshipped over here!) for sticking their necks out at the top level, risking their reputations and careers to see if they were good enough. Hat's off, too, to guys like Rodney Rogers, Stuart Holden, Jonathan Spector, Frankie Simik and others laboring in semi-obscurity in the English leagues when they could be making a comfortable living (like Donovan) back in the states.
... and Stuart Holden is the best American outfield player currently working in the EPL. Look at Bolton's winning percentage when he's in the squad and when he's out.