The Brewers had really good luck in the 2000's with a high draft pick spent on the son of a longtime former major leaguer, getting 6+ seasons of Prince Fielder. Unfortunately those picks don't always work out, and Tony Gwynn Jr. is a perfect example of the opposite.
Gwynn the Younger was 26 years old and a career .248/.300/.298 major league hitter on this day in 2009 when the Brewers gave up on him and traded him to the Padres. Gwynn was (and still is) a very solid player defensively and his AAA numbers (.309/.387/.395 in 38 games for Nashville before the trade) suggested that he might have turned a corner offensively, but the Brewers could no longer afford to wait for him to figure it out.
Since leaving the Brewers Gwynn hasn't done a lot to make the front office regret their decision. He's hitting reasonably well for the Dodgers this season but is still just a .250/.325/.335 hitter over 410 games since leaving Milwaukee. Of course, the Brewers didn't get much for him either: Outfielder Jody Gerut hit .224/.279/.371 over two seasons as a Brewer (hitting for the cycle once) and is now out of baseball.