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I was rebuilding the Pirates and I actually traded for Ellsbury in challenge mode. And the Yankees had no issues eating a huge portion of his salary. Forget what I gave up but it was peanuts.
Needed to actually start him. He did good and I was able to flip him at deadline for a middling prospect since he was basically free for that team.
So you can do the opposite. You should be able to move if you either eat huge salary or trade him to a team that has enough payroll but include a decent prospect and get a lesser prospect in return. You at least clear the money off of your books.
Of course you have to hope your trading partner has recently lost an OF and is in a Win It Now mode to help you out. If not you might get stuck giving up a higher grade prospect and basically getting dead weight back.
Or yeah look for a contract that expire the current year. Even if its bigger then his. If its off the books this season who cares how much it is.
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