The Best and Worst Trade of the Decade for the Chicago Cubs

After more than a century of pain and heartbreak, the 2010s finally brought the Chicago Cubs and their fans a long-awaited World Series Championship in 2016. The emergence of Kris Bryant, Javier Baez, Anthony Rizzo, and others rewarded the patience and perseverance of Cubs fans everywhere who had been longing for a World Series title for so very long.

The Cubs made the most of their championship window that general manager Theo Epstein built. It now appears that the window may be closing, as they will face several difficult roster decisions going forward. The deals that Epstein and the Cubs have made over the last decade, for better or worse, did result in the ultimate prize. The question is will one World Series title make those deals worth it?

Over the next several weeks Baseball Essential will be doing a series on the best and worst trade every team in Major League Baseball has made over the last decade. Here is the best and worst trade the Chicago Cubs have made since 2010.

The Best Trade the Chicago Cubs Have Made Since 2010: Chicago Acquires Anthony Rizzo and Zach Cates From the San Diego Padres for Andrew Cashner and Kyung-Min Na (January 6, 2012)

It is not an understatement to say that the trade that Theo Epstein made for Anthony Rizzo will go down as one of the greatest heists in baseball history.

Rizzo was 22 years old at the time of the trade and regarded as one of the Padres’ best prospects; he had just arrived in San Diego as the centerpiece of the deal that the team made with the Boston Red Sox that saw the exit of All-Star first baseman Adrian Gonzalez.

The Padres were looking to bolster their starting rotation at the time, hence why they had their sights set on 24-year-old Andrew Cashner. While Cashner had not established himself as a starter quite yet, he showed flashes of tremendous potential during his brief time in the majors with the Cubs. Cashner, a 6-foot-6 hard-throwing right-hander, showed off a lively fastball and a promising amount of swing-and-miss stuff. His time in San Diego after the trade was frustratingly limited due to injuries, and the potential he showed in Chicago never fully came to fruition. Cashner wound up going just 28-43 with a 3.67 ERA in five years with the Padres before he was dealt to the Miami Marlins in 2016, the very same year that the Cubs would go on to win the World Series.

Rizzo, by contrast, saw his career launch off to new heights with the Cubs. Rizzo had four straight seasons from 2014-2017 in which he hit 30-plus home runs and compiled 150-plus hits, earning All-Star honors in three of those seasons. He is one of the most beloved players in Chicago to the point where fans even campaigned to have him wear a captain’s ‘C’ on his uniform.

Rizzo was an integral part of the Cubs’ 2016 World Series-winning team, hitting .292 and smashing 32 home runs that season. There are rumblings that his time in Chicago may be coming to an end due to the club options on his contract for the next two seasons. Nevertheless, Anthony Rizzo will forever be immortalized in Chicago Cubs’ history thanks to the incredible eight seasons he has had since being traded there.

The Worst Trade the Chicago Cubs Have Made Since 2010: Chicago Acquires Ian Stewart and Casey Weathers From the Colorado Rockies for DJ LeMahieu and Tyler Colvin (December 8, 2011)

This is absolutely a trade that Theo Epstein wishes he could go back in time and undo. Ian Stewart, who was 26 years old at the time of the trade, had just two years of decent production with the Rockies, but the Cubs were willing to roll the dice on him, nonetheless. LeMahieu, meanwhile, was tearing the cover off the ball in the Cubs’ Triple-A affiliate in 2011, hitting .319 with 25 extra-base hits that season in the minors.

Unfortunately for LeMahieu, the Cubs valued the defense that Darwin Barney provided on an everyday basis at the time, thus blocking him from reaching the major-league level. After the trade, LeMahieu remained in Colorado’s minor-league system for the first half of the 2012 season before eventually being called up to the big-league club. From 2013-2018, LeMahieu was one of the Rockies’ most consistent hitters, batting .299 and amassing over 1,000 hits in seven seasons. However, his best season came in 2019, his first year with the New York Yankees. He finished with a .327 batting average and a career-high 26 home runs which saw him finish fourth in American League Most Valuable Player voting.

LeMahieu is just 30 years old and figures to lead the 2020-2021 free-agent class once baseball activities resume.

The Ian Stewart experiment, on the other hand, could not have been more of a disaster for the Cubs. Stewart played in just 55 games with the Cubs that season, batting .201 with just five home runs. To make matters worse, Stewart proved to be a problem child off the field, constantly complaining about his lack of playing time. Stewart went to Twitter and ranted about his playing time, which led to the Cubs suspending him in the middle of the season for his poor behavior.

Ian Stewart, to the shock of no one, is no longer in major-league baseball, as his career quickly fizzled out after the 2014 season. DJ LeMahieu, meanwhile, has put together an incredibly impressive resume over his nine-year major-league career. Should he keep playing at this level, he may very well establish himself as one of the greatest second basemen of all time when all is said and done.

Stay tuned to Baseball Essential over the next few weeks for more on the best and worst trades made by all 30 MLB clubs over the past 10 years.

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