Michael Young and Derek Jeter are two of the worst everyday shortstops in recent history. And yet, Young and Jeter have now captured four of the last five American League Gold Gloves. Honestly, this is pretty mind-blowing (unless you've been paying attention to the Gold Glove results for the last few years, in which case it should be pretty hard to blow your mind). From 2004 through 2007, Young was roughly the 30th best shortstop in the majors. Over those four years, he was roughly 100 plays worse than the average major league shortstop. This year he improved some, and might have cost his team only 10 hits rather than 20 or 30.
Sure, it might have been a one-season fluke, but you have to give the guy credit for doing better. You don't have to give him an award suggesting he's the top defensive shortstop in the American League.
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As for Young, it's actually not hard to figure out how he won. He had another big year with the bat (which voters like) and he led the American League in fielding percentage (which they absolutely love). My friends, I give you the American League's Nate McLouth.