5: Wouldn't that push Ankiel off the list?

The Brewers traded flameout pitching prospect Ben Hendrickson (whose last game in the majors was also hard to watch) to the Royals just before the 2007 season for Quebecois catcher and career minor-leaguer Maxim St. Pierre (anagrams: "Marxist Empire" and "Primates Remix").

MSP had begun his pro career ridiculously young, turning 17 less than two months before the 1997 draft that saw the Tigers take him in the 26th round. He'd played his whole career, ten years, for Detroit before signing with Kansas City as a free agent only a couple months before the Hendrickson trade. He played in just ten games for Milwaukee's AA affiliate, Huntsville, before, as I recall, quitting to become a pitcher. He was 27 at this point.

I don't remember what happened to his nascent pitching career, but come 2008 St. Pierre was back catching in Detroit's system, and he was eventually rewarded with six games in the majors with the Tigers in 2010. He even got a couple hits, including bagging a two-bagger (career .248 MiLB average).

Now, what's especially interesting to me is that, after quitting or being let go by the Tigers after 2011, he kept playing in the independent Can-Am Association, for his hometown Capitales de Quebec--but exclusively as a pitcher. He pitched (terribly) in 11 relief appearances last year while not recording a plate appearance, but he did notch a win. Looking at his career from 1997-2009, I don't think you'd predict either an MLB double or a profession win in his future, but baseball is a funny game.