5 best moves made by the late St. Louis Cardinals general manager Walt Jocketty

3. Trading for starting pitcher Adam Wainwright (2003)

Trading away an All-Star outfielder in the prime of his career is certainly a bold move. For Walt Jocketty, it was a gamble that paid dividends for two decades.

When Jocketty traded J.D. Drew in the 2003-2004 offseason, he saw a very talented player who was injury-prone in Drew. Therefore, he found it a pill he could swallow regarding the trade that landed Jason Marquis and a young pitching prospect known by the name of Adam Wainwright. At the time, Wainwright was the Braves' top pitching prospect and a former first-round pick.

Wainwright took two years after the trade to make it to the majors, and he started his career as a reliever in St. Louis. In fact, Wainwright's closing of Game 5 of the 2006 World Series is iconic. Images of him catching backstop Yadier Molina in an embrace are ingrained into the minds of Cardinal fans.

Wainwright played every one of his 18 years with the Cardinals, and his 47.6 fWAR total trails only Bob Gibson among pitchers in franchise history. Wainwright finished in the top 10 of National League Cy Young voting five times during his career, including second-place finishes in 2010 and 2013. Wainwright underwent Tommy John Surgery in 2011, and he missed the entire season as a result.

Wainwright finished his career with a 3.54 ERA, 2,202 strikeouts, and a 200-128 record. He recorded his 200th win in his final start against the Milwaukee Brewers in St. Louis on September 18th, 2023.

While Wainwright's case to be in the National Baseball Hall of Fame is questionable, he's a lock to be a Cardinal Hall of Famer when the time comes. Without the trade that sacrificed one of the best outfielders in the game in the early 2000s for a tall righty with a wicked curveball, the Cardinals could be sitting at 10 World Series titles.

Walt Jocketty took a gamble trading J.D. Drew for Adam Wainwright, and it paid off handsomely for both him and the St. Louis Cardinals.