No. 5: Minnesota Twins swap an All-Star for a Cy Young Winner
Result: +19.7 WAR
Analysis: In the Twins third season in Minnesota, the team decided to trade a slightly more consistent pitcher for a slightly more talented one, swapping Kralick for Perry, who was in the midst of a disappointing season.
This trade ended up being huge for the Twins, as while Kralick was an All-Star, Jim Perry became a Cy Young winner and one of the greatest pitchers in Twins history, an elite starter who helped lead the team to its first pennant in Minnesota.
No. 4: Minnesota Twins grab the Ultimate Utility Man
Result: +23.7 WAR
Analysis: Gerry Arrigo was a pretty decent swingman pitcher once he was traded away from the Twins, but thats nothing compared to the player the Twins got back. Cesar Tovar became a Twins All-Time great.
Tovar finished in the Top 25 of MVP voting five times with the Twins, all while stealing 186 bases and playing every defensive position imaginable for the team. He also hit .281 over his eight year in Minnesota, making him one of the top 5 centerfielders in team history.
No. 3: Minnesota Twins trade away their ace
The Trade: Minnesota Twins trade P Frank Viola (9.8 WAR) to the New York Mets for a player to be named later (P Jack Savage (-1.1 WAR)), P Rick Aguilera (15.5 WAR), P Tim Drummond (1.0 WAR), P Kevin Tapani (19.1 WAR) and P David West (0.0 WAR).
Result: +24.7 WAR
Analysis: It’s not very often that you see the reigning Cy Young award winner traded the very next season, and for the Mets to get him they needed to offer the Twins a huge package of young arms in order to acquire him. That’s exactly what they sent.
Though Savage and West turned out to be duds, Kevin Tapani and Rick Aguilera became key pieces of the Twins team that would win a World Series just two years later. In addition, Aguilera also made three All-Star teams, while Viola had two solid full seasons with the Mets before signing with the Red Sox in free agency.
No. 2: Minnesota Twins completely rob the Giants
Result: +27.1 WAR
Analysis: The other 2000s trade on this list, and probably the most infamous trade on this list, the Twins completely fleeced the Giants when they traded away All-Star catcher A.J. Pierzynski and got three young pitchers in return.
Boof Bonser never lived up to his first round billing, but Fransisco Liriano became an All-Star and a fixture in the Twins rotation. In addition, the third pitcher, Joe Nathan, the Twins acquired was moved to the closer role and became one of the greatest closers of all-time.
Pierzynski on the other hand was released at the end of the season after clashing with coaches and becoming a very unlikable figure in the league. This all ends with the Twins coming out as huge winners in this deal.
No. 1: Minnesota Twins swap Rule 5 Picks
Result: +35.8 WAR
Analysis: In 1999, the Twins had the No.1 pick in the Rule V draft and the Marlins had the No. 2 Pick. The Twins wanted Johan Santana, and the Marlins wanted Camp, but other teams were making the Twins offers.
The Twins decided to draft Camp and trade him to the Marlins for Santana and $50,000 to cover their pick costs. Camp never made the majors, and as we know, Santana became one of the greatest pitchers in Twins history.
Santana’s three year run from 2004-2006 is the greatest in Twins history and possibly ever, and the Twins got Santana for a player who would never make the major leagues, making this the most lopsided trade for the Twins ever.