A Brief History of Trades Between the Red Sox and White Sox

If started talking about that time the Red Sox acquired a top-of-the-rotation, left-handed pitcher from the Chicago White Sox for a package of prospects, you would have to ask further questions to figure out which trade I was talking about. Maybe I’m talking about Garrett Crochet. Maybe I’m talking about Chris Sale. Or maybe I’m talking about the 1970 trade for Gary Peters. When two franchises have been around for as long as the Red Sox and White Sox, there is sure to be a long history. Here are just a few of the biggest moves the sides ever matched up for.

Future Hall of Famer Harry Hooper had the best season of his career in 1920. The following season, the Red Sox shipped him out of Boston to the South Side of Chicago in return for Shano Collins and Nemo Leibold. Shano Collins was a Massachusetts native and certainly hadn't had a bad career up until that point, and Nemo Leibold posted 1.6 WAR the next year. But neither compared to Hooper, who put up 14.9 WAR for the White Sox in his final five seasons.

In the 1950s, the Red Sox traded another future Hall of Famer, George Kell, to the White Sox for Grady Hatton and $100,000. This is a little less egregious than the Hooper trade, because Kell wasn’t a career Red Sox beforehand. He is mostly known for his first nine seasons with the Philadelphia Athletics and Detroit Tigers. Still, Kell posted 5.4 WAR over three seasons with the Red Sox, then 3.4 WAR over the next three seasons in Chicago.

The next time the two teams matched to move a future Hall of Famer, Boston was on the receiving end. They got Luis Aparicio for the final three seasons of his career in exchange for Luis Alvarado and Mike Andrews. While Aparicio posted 4.2 WAR for the Red Sox, Alvarado never accumulated positive WAR for Chicago and Andrews only had one positive WAR season in 1971 racking up 1.7 WAR.

In 1986, the Red Sox and White Sox did a one-for-one swap: Boston received future Hall of Famer Tom Seaver for occasional NESN studio analyst Steve Lyons. Despite trading him away, the Red Sox would re-acquire Lyons two more times before he retired with Boston in 1993.

In more recent times, the Red Sox actually have a history of receiving fairly important pitching pieces from the White Sox. In 2006, Boston received Javier López from the White Sox in exchnge for David Riske. López would go on to pitch in the 2007 World Series for Boston, mostly as a left-handed specialist.

In 2013, the Red Sox, White Sox, and Tigers worked out a three-team trade that netted Boston Jake Peavy. Although Peavy ran a 7.11 ERA in three postseason starts, he was a major reason that the Sox made it there, and he even bought a duck boat after they won the World Series. 

That brings us to the Chris Sale trade, in which the Red Sox gave up Victor Diaz, Luis Alexander Basabe, Michael Kopech, and Yoán Moncada. At the time, many Red Sox fans thought it was a massive overpay, but Diaz and Basabe never made the majors with the White Sox and neither Kopech nor Moncada ever really reached their full potential. Although Sale’s tenure with Boston was injury-filled, it is hard to imagine the Red Sox winning the 2018 World Series without him.

And that brings us to the Garrett Crochet deal. The Red Sox sent Wikelman Gonzalez, Chase Meidroth, Braden Montgomery and Kyle Teel to Chicago for Crochet. Sale had over 1,200 career strikeouts and had accumulated 30.1 WAR when he was moved to Boston. Crochet has a career 5.9 WAR and only one full season as a starting pitcher. Still, if the Sale trade has taught us anything, it is that four prospects — no matter how highly touted — are still lottery tickets, not guaranteed to hit. Will Crochet go on to be a Hall of Famer like Tom Seaver or a Hall of Very Good pitcher like Jake Peavy? Only time will tell. But if he helps the Red Sox win the World Series, no one will worry very much about what the team gave up for him.