#3 - Adam Wainwright (2003)
Cardinals acquire: RHP Adam Wainwright, RHP Jason Marquis, and LHP Ray King
Braves acquire: OF J.D. Drew and OF Eli Marrero
Total surplus fWAR: 44.0
The top three are in pretty exclusive company in Cardinals history. While Adam Wainwright will likely miss out on Cooperstown when voting comes around, he is forever a Cardinals legend and one of the best pitchers of all time, and it took a bold trade by Walt Jocketty to make him a career Cardinal, rather than an Atlanta Brave.
Prior to the 2004 season, Jocketty had some tough decisions to make regarding their roster. J.D. Drew was one of the best young outfielders in baseball talent-wise, but had yet to reach 500 plate appearances in a season due to injuries and was one year away from free agency. With the MV3 already locked in and other pieces around them, Jocketty opted to flip Drew for pitching depth that included RHP Jason Marquis, LHP Ray King, and a top 50 prospect in baseball, RHP Adam Wainwright.
Drew went on to have an incredible 2004 season for the Braves, posting an 8.6 fWAR and 162 wRC+ en route to finishing sixth in MVP voting, behind third, fourth, and fifth-place finishers Pujols, Rolen, and Edmonds. Drew left Atlanta after the 2004 season to sign with the Los Angeles Dodgers and played seven more seasons combined for Los Angeles and the Boston Red Sox.
While Drew had a great big league career, the Cardinals feel really good about how the deal panned out for them in snagging Wainwright for their club. Wainwright went on to pitch 18 seasons for the Cardinals at the Major League level and went down as one of the best pitchers in franchise history.
Wainwright's first full season with the club came in 2006, where he became a critical part of their bullpen and then filled in as the club's closer when Jason Isringhausen went down with an injury late in the year. Wainwright was masterful during the 2006 playoffs, appearing in nine games out of the bullpen while recording four saves and not allowing a single run in 9.2 innings pitched. Wainwright recorded one of the most iconic moments in postseason history when he struck out Carlos Beltran looking in Game 7 of the NLCS to advance St. Louis to the World Series.
Following the 2006 season, Wainwright entered the Cardinals' rotation and was almost immediately one of the best pitchers in all of baseball. From 2007-2015, Wainwright pitched in 224 games, going 119-66 with a 2.96 ERA and 1254 strikeouts in 1492.2 innings pitched. Wainwright had the sixth best ERA among starters over that stretch and record the 11th most fWAR, and that's while missing the entire 2011 season and most of the 2015 season due to injuries, Had Wainwright not been robbed of those two years of his prime, I think he is easily a Hall of Famer.
Wainwright also ran into some terrible luck when it came to Cy Young contention. In 2009, Wainwright actually received the highest percentage of first-place votes, but his teammate, Chris Carpenter, took first-place votes away from him, and thus, Tim Lincecum bested both of them for the Cy Young that year. Then in 2010, he finished runner-up to Roy Halladay, who put up a truly historic season, and then Wainwright missed the following year due to Tommy John surgery.
In his return season from that major injury, Wainwright was incredible, going 19-9 with a 2.94 ERA in 241.2 innings of work, but finished second to Clayton Kershaw in perhaps Kershaw's best season of his career. Then, Wainwright would finish third in Cy Young voting again in 2013.
Again, had Wainwright captured one of those Cy Young awards, he's probably a surefire Hall of Famer.
Wainwright did manage to make it into the 200-win club, something that may not happen again in today's game due to the nature of how it's played now. Wainwright ranks second all-time amongst Cardinals starters in strikeouts and third in wins and innings pitched. Without Wainwright, the Cardinals are a far less successful team in the 2000s and 2010s.