Because the guy traded key parts of a core unit that got the Dodgers to an 8 game lead in the division, when no one expected them to do more than 3rd, for a guy with known arm problems. Hee Sop Choi wasn't going to be playing this year, and the minor league pitcher they got was tradebait for Finley. Basically all we got for LoDuca (.300 hitting cathcer & leader), Mota (nails setup man to Gagne), and Encarnacion (solid platoon outfielder, great defensively, got some clutch hits), was Brad Penny. You're going to mess with your cheminstry, bullpen and lineup that late in the season for a guy that's going to see action once every 5 days? That's if his arm troubles don't pop up. Depodesta touted the trade as what was going to get them not only into the playoffs, but deep into the playoffs
this year.
So what happened? Dreifort was put into a positioin he was clearly not ready for, got hurt and now the bullpen is a mess, resulting in starting pitching to have to go more innings, and thier current starting pitching woes are a consequence. Not only that, but you take 2 bats out of your lineup and replace them with a streaky Finely, who when he's hot he's rediculous, but right now he's not at all on, and non-factors Maine and Ross, you get an inept offense reliant on longball to overcome 3-5 run leads caused by the starting pitching faultering, and you can see where this becomes a circle and where it leads.
All would have been forgiven if Depodesta could have convinced Randy Johnson to come to LA, but he rolled the dice and came up duece. So we have to settle for Penny. Defenders of the trade will bring up Finley, which was a great deal, but I maintain that we could have gotten Finely and kept LoDuca and Mota, after all, Arizona traded him for 2 minor leaguers.
But all that's history now, we have to deal with it. I think the bitterness though comes from the feeling that Depodesta traded away a fan favorite, revisiting the Piazza debacle and messing with an amazing chemistry that got them to where no one in their right mind would have thought possible. And if you think chemistry doesn't matter, watch the NBA Finals of last year
Sorry about the rant, I didn't have internet access around the time the trade went down, so I had this all suppresed, glad I got it out
That's basically my take on why Depodesta is not looked at with high esteem right now.