What if he goes to a town with a recent history of losing, like Pittsburgh or Tampa Bay? Does it matter what the press is like if there's no history of GM success? Although there's only a couple of places that fit that description that don't have recent "savior"-esque GM hirings.

The Baltimore job might have been best for both DePo and for Angelos. DePo gets a huge payroll to work his magic with, and as soon as Angelos wants him gone, he can win a media war.

Was it that DePodesta was so bad at handling the media, or that a few LA Times writers were out to get him from the start because of his portrayal in Moneyball? Either way, why would fans or an organization care what morons like Bill Plaschke said as long as a GM got results?

I'd love for DePo to take over for Cashman next season.

Or you can add a press barrier to the front office. Much as NFL GM's have Cap specialists on staff. Additionally, I think Adam makes a good point. Plaschke was on a jihad, and got his head.

pat gillick constantly sends assistant gm ruben amaro onto local tv. depodesta could just do something similar.

Bill Plaschke's a moron, but as the senior sportswriter at the L.A. Times, he's got pull in this city's sports world. It's not a good thing, but that's how it is.

The problem with Drew's contract wasn't so much that he had an escape clause after two years, but that the Dodgers never had an option to opt out of the contract at any time. If Drew had decided to stay after the 2nd year, then the Dodgers would have been on the hook for another 3 years to a dog of a player. Depo, like many GMs before him, got snookered by the brilliant Scott Boras.
On the issue of his not being able to deal with the press, I think this is overblown. Lots of GMs are not press friendly. Whatever positive skills Depodesta brought to the job were undercut by his inability to deal with personal in the organization. It was well known his people skills were below par for someone in his position.