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I've never used draft pick trading, although I would be curious to know how the AI values high picks. Having no idea how good/bad San Diego might be... how easily would they sacrifice a high pick for a prospect that hasn't cut the mustard at any level?
As far as bad contracts, in my experience the AI does a god job at trying to move them. Swapping bad contracts is something that doesn't seem to happen a ton in the majors, but it can be a help in OOTP. I recently moved an awful contract for an over the hill starter who didn't have a spot on my 25 man. At best, he was a 4th or 5th starter on an awful staff, probably long relief for most teams... But I found a team that offered up a catcher with an equally awful contract. They had no pitching, I had nobody to play backup catcher... So we both turned awful contracts for guys that would have likely passed waivers and rotted in triple A into awful contracts that will at least make the team.
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