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.
Today is also the ninth anniversary of Geoff Jenkins hitting three home runs as the Brewers beat the Padres 10-0 in 2003. We covered that event in this space last year.