I considered multiple trades in this spot, including a 3-team mega blockbuster that would have sent Adrian Gonzalez, Clay Bucholez, Daniel Bard, and Heath Bell to the Mariners and Felix Hernandez to the Red Sox. The Padres would have received Carlos Truifinel and Brandon Morrow. Morrow is good but not as good as any of the 5 above. The trade I did end up choosing was:
In 2009 the Padres were scuffling and dealt their ace Jake Peavy to the Chicago White Sox in exchange for LHP Clayton Richard and prospects. The deal that didn't go through was a blockbuster. Adrian Gonzalez and Heath Bell would be sent to the Los Angeles Dodgers in exchange for five players. James Loney, Ivan Dejesus Jr., Russel Martin, James McDonald, and Blake DeWitt.
This deal could have turned out to be one of the better Padres deals, or possibly the worst padres trade ever. Martin was considered a star catcher with speed, power, and a pure bat. .300 26 HR 30 SB was not out of the question. He'd have been our replacement Gonzalez. He flopped with LA from then and on. A trade may have woken him up like becoming a Yankee did.
James Loney was considered the best defensive 1B in the minors, and possibly being a .300 20 HR bat at first. Over the last 1 and a half years he has been essentially replacement level. He has been better than Padres 1B's but not even close to Gonzalez. Jesus Guzman, who has about 25 at bats, has 1/4 of the HR that Loney has. Loney has 281 at bats.
James McDonald was expected to be what he turned out to be...in Pittsburgh. Essentially he was supposed to be like Matt Garza, a flamethrower with lots of K's and a good ERA. He flopped in LA so they packaged him with Andrew Lambo and traded them for Octavio Dotel. Dotel pitched a half a month with them, before being shipped to Colorado for a PTBNL. McDonald and Kevin Correia lead Pittsburgh's rotation.
Ivan Dejesus Jr. was a top prospect, like Jose Ingleas, who could play defense. He got hurt and is toiling away at AAA Albuquerque (I love spell check). Another flop.
Blake DeWitt only provided two positive things to any team in MLB, both were too LA. He had a fantastic rookie year, on a full season's pace he would have hit 15-18 HR and around .270. LA traded him to Chicago for LHP Ted Lilly and SS Ryan Theriot. Theriot was then traded for Blake Hawkensworth. LA ended up with a solid lefty and a young pitcher with upside.
In a summary, this would have been a poor trade if all of these players flopped like they did in LA, but maybe if they were traded, it would keep them out of their slumps.