Chicago Cubs: Comparing the Cubs and White Sox rebuilds

Cubs Trades

The first step for both rebuilds was to sacrifice the veteran talent in order to shed the payroll and accumulate losses (and in turn, higher draft picks). Let’s look at the Cubs’ trades first.

Andrew Cashner for Anthony Rizzo (January 6, 2012)

Not longer after Theo and company arrived in Chicago, the Cubs sent pitching prospect Andrew Cashner and minor leaguer Kyung Min-Na to the San Diego Padres in exchange for first baseman Anthony Rizzo and pitching prospect Zach Cates. Rizzo, who was drafted by the Red Sox organization in 2007 and sent to the Padres in 2010. He had essentially followed the trio of Epstein, Hoyer and McLeod at their three stops together between Boston, San Diego and Chicago. Rizzo quickly became the centerpiece for the organization to build around.

Ryan Dempster for Kyle Hendricks and Christian Villanueva (July 31, 2012)

A long-time fixture in the Cubs organization, the Cubs sent Ryan Dempster to the Texas Rangers at the trade deadline for young prospects Christian Villanueva and Kyle Hendricks. Though Villanueva never saw any time as a Chicago Cub at the major league level, Hendricks made an immediate impact upon reaching the bigs in 2014 and has remained a key component of the Cubs starting rotation ever since.

Steve Clevenger and Scott Feldman for Jake Arrieta and Pedro Strop (July 2, 2013)

Though it didn’t seem all that significant at the time, the acquisition of pitchers Jake Arrieta and Pedro Strop from the Baltimore Orioles for Steve Clevenger and Scott Feldman would go on to be one of the most pivotal moves that the front office would make en route to contention. While Arrieta would be a key component of the rotation through 2017, Strop remains an enormous asset of the bullpen for the Cubs.

Jason Hammel and Jeff Samardzija for Addison Russell, Dan Straily and Billy McKinney (July 4, 2014)

Arguably the biggest blockbuster trade of the Cubs rebuild, the Cubs sent starting pitchers Jeff Samardzija and Jason Hammel to the Oakland Athletics for top prospects Addison Russell and Billy McKinney (plus Dan Straily). In retrospect, the Cubs clearly won the trade as the A’s fell short of the World Series and Hammel returned to the Cubs for the 2015 and 2016 seasons.

Jeferson Mejia and Zack Godley for Miguel Montero (December 9, 2014)

The Cubs added some veteran leadership and a reliable backstop during the 2014-15 offseason by shipping away Jeferson Mejia and Zack Godley for long-time Diamondbacks catcher Miguel Montero. Miggy would go on to play a pivotal role not just as a catcher but most importantly in delivering what would be the game-winning hit in the 2016 World Series.

Luis Valbuena and Dan Straily for Dexter Fowler (January 19, 2015)

With young prospect Kris Bryant soon to arrive at the Friendly Confines, the Cubs traded away third baseman Luis Valbuena to the Houston Astros for veteran center fielder Dexter Fowler. With it came the end of the rebuild and the commencement of the team’s contention for the playoffs.