The most frustrating part of keeper-league managing, for me, is realizing that I gave up on a player too early. Holding on to a player while he goes through his growing pains could try anyone's patience, but there's nothing worse than compounding a bad rookie or sophomore effort by releasing, trading -- or not trading for -- a player on the verge of his breakout season.
My favorite example -- and I use the word "favorite" very loosely -- of giving up on a player too early followed the 2000 season, when after a brutal performance, I cut a former first-rounder who had been a Baseball America darling for years. Who could have blamed me? He'd pitched 67 1/3 innings and posted some of the worst numbers you'll ever see for a pitcher with at least 10 starts. In 19 appearances, 13 of them starts, he'd surrendered 80 earned runs on 14 home runs, 107 hits and 42 walks. That's a 10.64 ERA and a 2.20 WHIP in exchange for four wins and 44 strikeouts.
The player was sent down to Class A to fix what was wrong with his delivery and between his ears. He was called back up in 2001 and I begrudgingly placed a minimum bid on him. I lost him to my nemesis in that league, by a dollar. I still remember the e-mail he sent to the league: "Dammit, I thought Pete would save me from that one." He didn't want him either. Nobody wanted him. I probably could have traded for him for a middling minor league prospect. No way. My nemesis was stuck with this clown and had saved me from myself.