Chicago Cubs History: Longtime Cubs who turned into Cardinals

Ask a Chicago Cubs fan in 2016 how they would feel if they saw World Series hero Jon Lester pitching in a Cardinals uniform one day. The reaction would probably include cringing and denial of such a thing. Fast forward to 2021 and Lester indeed became a member of the Cardinals via trade from the Washington Nationals and pitched against the Cubs at Wrigley Field on Saturday.

Despite calling the visiting dugout home this weekend, Cubs fans still welcomed him back to Wrigley with open arms. During game one of Friday’s doubleheader, Lester was honored by the Cubs via video board message congratulating him on his 200th career win. Lester picked up his that landmark victory against the Brewers in Milwaukee on September 20.

Lester is one of many fan favorites from the North Side to eventually find his way to St. Louis. Whether it was toward the end of their careers, or still in their primes, it was hard for Cubs fans to watch these former heroes end up with Chicago’s biggest rival. Here is a look at some longtime Cubs who later put on Cardinals red. The basic criteria for this list is that these players had to play with the Cubs before the Cardinals, and they had to spend more time in Chicago than St. Louis. So spoiler alert, Lou Brock will not be included on this list.