Cubs Reflect on Their Most Disastrous Trades of the 21st Century

CHICAGO, ILLINOIS - As night falls on the city, BCB After Dark offers a welcoming space for Cubs enthusiasts, night owls, and anyone seeking a relaxed atmosphere to discuss their favorite topics. With no entry fee and a laid-back vibe, fans are encouraged to share their thoughts on baseball, music, movies, and more.

In a recent discussion, readers were invited to weigh in on the best trade made by the Cubs in the 21st century. The majority picked the acquisition of Jake Arrieta and Pedro Strop, garnering 53 percent of the votes, while the trade for Anthony Rizzo followed with 22 percent. As time goes on, fans may find that the deal for Pete Crow-Armstrong also holds significant promise, but its impact remains to be seen.

Shifting focus, the conversation turned to the Cubs' worst trades of the century, a topic that can be challenging for fans but necessary to address. Every franchise has its share of successes and failures, and the Cubs are no exception. A few notable missteps stand out, beginning with the July 7, 2008 trade that sent Josh Donaldson, Sean Gallagher, Matt Murton, and Eric Patterson to the Athletics in exchange for Rich Harden and Chad Gaudin. Although Harden had a strong finish to the season, Donaldson later emerged as a standout third baseman and 2015 MVP.

Another regrettable trade occurred on July 30, 2009, when the Cubs dealt Josh Harrison, José Ascaino, and Kevin Hart to the Pirates for Tom Gorzelanny and John Grabow. Despite trying to salvage a disappointing season, Gorzelanny's performance fell short, and Harrison went on to have a successful career as a two-time All-Star.

Lastly, the December 8, 2011 trade that sent DJ LeMahieu and Tyler Colvin to the Rockies for Ian Stewart and Casey Weathers marked a low point for then-President of Baseball Operations Theo Epstein. LeMahieu would go on to achieve significant accolades, including two batting titles, while Stewart's tenure with the Cubs was marred by poor performance and a negative attitude.