The Cardinals give up quite a bit to land Scott Rolen in 2002, but it pays off.
This trade is actually a bit more balanced than the others on this list, but Scott Rolen's place as a part of the "MV3" in St. Louis makes the scales tip in favor of the Cardinals. In order to land the hot corner maestro, The Cardinals had to send Placido Polanco, Mike Timlin, and Bud Smith to the Philadelphia Phillies for Scott Rolen at the 2002 trade deadline.
Placido Polanco went on to have a great career, and despite only playing in Philadelphia for three total seasons, he was able to accumulate nearly 10 fWAR in that time. Polanco was a premier infielder for his time. Mike Timlin didn't provide much value to the Phillies, and Bud Smith was out of baseball soon after the trade.
Scott Rolen would go on to play five and a half years in St. Louis, win a World Series in 2006, accumulate 27.2 fWAR, attend four All-Star Games, and receive three Gold Glove Awards. Rolen's best year of his career came in 2004 when he had a 1.007 OPS, a 158 OPS+, 34 home runs, 124 RBIs, and a Gold Glove. He would finish fourth in National League MVP voting that year. Rolen was elected to the Hall of Fame last year.
Rolen's heights, consistency, and defense made this deal one for the ages for the Cardinals. They sacrificed a steady infielder in Polanco, but what they got out of Scott Rolen in his peak years was matched only by his teammates, Jim Edmonds and Albert Pujols. His contributions to the 2006 World Series team were essential, and this trade will go down as one of the best deals at the deadline for the franchise.