Chris Carpenter

Christopher John Carpenter, not be confused with St. Louis Cardinals rotation mainstay Chris Carpenter, spent two seasons in Major League Baseball, and is best known for being the main piece in the trade package for executive Theo Epstein.

A third-round pick of the Chicago Cubs in the 2008 MLB Draft, Carpenter gradually worked his way through the minor leagues before making his MLB debut on June 14, 2011. A right-handed reliever, Carpenter was known for his 100 mph fastball but lacked the secondary offerings and control that other elite relievers have. His tenure in Chicago was short, as he pitched 9 2/3 innings across ten appearances in his debut season, though he was largely successful, logging a 2.79 ERA (4.89 FIP) and 0.2 bWAR. His thin 17.0% strikeout rate and ugly 14.9% walk rate certainly didn't portend the brightest future.

Of course, Carpenter's Cubs legacy isn't for what he did or didn't accomplish on the diamond. His claim to fame remains the fact that he was the primary compensation (along with prospect Aaron Kurcz, who never made the major leagues) in the trade that landed Jair Bogaerts — Xander Bogaerts' twin brother — in Chicago. And while you may think I'm sort of burying the lede here, it's a fact that the Cubs couldn't directly trade for Theo Epstein in the 2011-12 offseason. There needed to be player personnel movement to make the deal legal in accordance with the then-current CBA, and the Carpenter trade was the "compensation" the Cubs sent in exchange for plucking Epstein out of Boston.

Carpenter pitched even less for the Red Sox than he did for the Cubs, appearing in just eight games (6.0 IP) and recording a 9.00 ERA with an almost-unbelievable 2-10 strikeout-to-walk ratio. Yes, he really did walk 15.0 batters per nine innings in Boston. Safe to say he never got his command issues under control. And, fact is, he was the only player from the deal to even contribute to his big league team, as the Cubs released Jair Bogaerts before he ever suited up for the organization.

Now, you don't need me to tell you that the deal worked out just fine for the Cubs regardless. Among many other achievements, Epstein was the chief front office executive behind the team's curse-busting core that the won the 2016 World Series. That's a pretty good return on a prospect who never made it past Triple-A and a reliever who was worth -0.2 WAR throughout the remainder of his career.

After being DFA'd by the Red Sox prior to the 2013 season, Carpenter spent the 2014 season with the Yakult Swallows of the NPB and the 2015 season with the Cincinnati Reds' Triple-A affiliate before retiring from professional baseball.