Revisiting the 2011 D.J. LeMahieu-Ian Stewart Trade between Cubs, Rockies

Eleven years ago, then-Colorado Rockies general manager Dan O'Dowd pulled the trigger on a franchise-altering trade, acquiring second baseman DJ LeMahieu from the Chicago Cubs in a four-player deal.

At the time, LeMahieu had played just 37 Major League games. He would go on to make three All-Star teams and win three Gold Glove awards and two Silver Sluggers.

The trade would lay the groundwork for the Colorado Rockies' playoff teams of 2017 and 2018, as LeMahieu, Nolan Arenado and Trevor Story would make up one of the best infields in baseball. The LeMahieu deal was one of the best trade heists of the 2010s, and one of the greatest trades in Colorado sports history.

On December 8, 2011, the Rockies traded infielder Ian Stewart and pitching prospect Casey Weathers. to the Cubs for outfielder Tyler Colvin and second baseman D.J. LeMahieu.

Weathers would never make it out of the minor leagues, and Stewart's Cubs tenure would prove to be a short one.

After breaking his wrist and slashing .201/.292/.627 over 55 games in 2012, Stewart would start the 2013 season in Triple-A Iowa, go on a Twitter rant criticizing the team, receive a suspension, and eventually be released by the organization.

LeMahieu, however, would go on to win two batting titles.

O'Dowd recently reflected on the trade in an appearance on the Jack Vita Show last week. When asked if he had a favorite free agent signing or trade that he had made in his 15 years as the Rockies GM (1999-2014), O'Dowd pointed to the LeMahieu trade, a move he says, nobody else in the front office wanted to make.

"The DJ LeMahieu trade for me probably is the one that I take great satisfaction in because not anybody on my team of people wanted me to do it," O'Dowd said. "But we still did it anyway. And I just have tremendous respect for everything that DJ represents within our game.

O'Dowd was quick to point out that he doesn't like to toot his own horn, and felt that signing free agents wasn't 'one of [his] greatest strengths.'

LeMaheiu, 22 at the time of the deal, slashed just .250/.262/.546 in 37 big league games in 2011. Though he struggled in a small sample size, LeMahieu had thrived at every level of the minor leagues.

So what did new Cubs president Theo Epstein see in the 26-year-old Stewart, coming off his worst season, slashing .156/.243/.464 in 48 games in 2011?

"In defense of the Cubs, Ian Stewart's talent level was just phenomenal," O'Dowd said. "I could see where he just got stuck behind Garrett Atkins, (and) we had (second baseman) Jeff Baker. It was like he was never given this ramp. So if I'm Theo and Jed (Hoyer), I get it. I get going, 'Well D.J.'s skill set is this, but if we hit on this guy in the rebuild that we're going into, we've got a superstar."

O'Dowd was on an island as the Rockies' lone front office worker who wanted to deal for LeMahieu.

"We didn't have a ton of internal people — in fact, we had none — at winter meetings in our scouting room — our Major League scouts and our analytical group — no one wanted to acquire D.J. except me," O'Dowd said. "And we did it."

So what made O'Dowd so certain that LeMaheiu was worth trading for? What caused him to go against the advice of his scouts and analytical group?

The answer, advice he received from former Cubs' GM Jim Hendry, a good friend of O'Dowd's.

Hendry had been fired by the Cubs new ownership group midway just months earlier, and replaced by Theo Epstein and Jed Hoyer. No longer employed by the Cubs, he offered some friendly advice to O'Dowd.

"I really trusted his baseball acumen," O'Dowd said. "So I called him up. And he just said, 'Dan, if you get a chance to get DJ LeMahieu, you ought to do so, because the guy is going to flat-out hit, but he's also everything you want and he's just scratching the surface of how good he can be. And I really trusted Jimmy's judgment. 

"(Jim) was the only one who really gave me any affirmation that it was the right deal to do on my end of it. He wasn't even working for us."

Over seven years in Colorado, LeMahieu, while playing elite defense at second base, would slash .299/.352/.760, appearing in two All-Star Games and winning two Gold Gloves.

Seven years removed from trading him to the Rockies, Cubs president Theo Epstein watched LeMahieu and his Rockies beat the Cubs in the 2018 National League Wild Card game.

Four years after O'Dowd turned down an extension to remain with the Rockies, LeMahieu would walk from the organization too, as a free agent, signing with the New York Yankees.

In both of his first two seasons with the Yankees (2019 and 2020), LeMahieu would finish top-4 in American League MVP voting and win a Silver Slugger award.

Ian Stewart, however, would make his final big league appearance in 2014.

Catch O'Dowd's full conversation about his time as the Rockies GM and the Indians assistant GM on the Jack Vita Show. He also discusses how baseball has changed, which rebuilding teams are close to turning a corner in 2023, and much more!