Sometimes, an owner can trade for a player and then realize after the fact that he doesn't like what he did. Or, in other instances, an owner can make a trade and then receive an offer for a more valuable player at the same position, and feel regret that he made the first trade.
This seems like an obvious piece of advice, but the best thing to do in these cases is to move on.
One owner in our league traded two of his minor league picks for Jeremy Guthrie at $10. After looking more closely at Guthrie, he decided he didn't like him as much as he thought he did. Instead of panicking, he flipped Guthrie for another minor league pick and John Danks at $2. Danks might be a poorer bet than Guthrie, but he's $8 cheaper and offers more upside to this rebuilding team.
The owner who acquired Guthrie got his hands on Jon Garland at $10 the next day. He didn't want to keep too many pitchers who were borderline freezes so committed to throwing Guthrie back. This same owner was then offered Dustin McGowan at $10. He froze at first, thinking that he had already acquired Guthrie, but realized that the opportunity to add another starter in an auction where the drop-off after Erik Bedard, Roy Halladay, and Daisuke Matsuzaka was incredibly steep was a chance he couldn't pass up.
Even in the off-season, you can't be timid and refuse to change tactics midstream if you get a better offer. If you trade for a player and you change your mind on that player, you can't keep him simply to save face.
The flip side of this is that you shouldn't make a trade for a player you're not sure about in the first place. The owner who got Guthrie had no other starting pitchers at that point and probably should have either passed on Guthrie or acquired another starter first before committing to Guthrie. Obviously, losing two minor league picks isn't a cardinal sin, but this is a trade he might have been better off not making.
The moral is never to feel trapped by your roster. I offered Casey Blake at $10 to an owner who had just acquired another third baseman, and had two third basemen plus a DH on his roster. He had nowhere to put Blake. But he then turned around and traded his DH away a few days later. He liked the offer for Blake, so he might have been better off analyzing Blake's value versus his weakest third baseman's value and deciding if the trade was worth making or not. If it was, he should have pulled the trigger. He would have been locked in at 3B/DH coming into the auction, but he might have had enough value to make this work.
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