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.

Chicago Cubs: Cy Young winner Rick Sutcliffe ended his career with the Cardinals

Veteran righty Rick Sutcliffe was a godsend for the Cubs when Dallas Green acquired him from the Cleveland Indians in 1984. His Cy Young award-winning efforts helped propel the team to the NL East title, followed by seven more years of quality pitching. Sutcliffe pitched with the Cubs through 1990, posting a 3.74 ERA, 3.60 FIP, 1.3 WHIP and 909 strikeouts in 193 games. He made two NL All-Star teams as a Cub in 1987 and 1989.

After his seven-and-a-half year run with the Cubs, he signed with the Baltimore Orioles in 1991. His two seasons with the Orioles did not go very well, pitching to a 5.00 ERA, 4.51 FIP and 1.5 WHIP in 65 games. In January of 1994, Sutcliffe made the move to St. Louis via free agency.

At 38 years old and in what would be his final season as an MLB pitcher, Sutcliffe returned to the Wrigley Field mound on June 26, 1994. Despite struggling mightily in the season, The Red Baron beat his former club with a six inning, one-run effort. He surrendered only four hits, struck out two and walked none in a 3-1 Cardinals win.

Sutcliffe finished his final season with a 6.52 ERA and 1.85 WHIP in 16 games. His Cardinals tenure was brief and forgettable. The 1994 season, of course, ended early with the infamous baseball strike.

Chicago Cubs: A former 1960s-1970s centerpiece spent some time in St. Louis

Don Kessinger was one of the most talented shortstops the Cubs had ever had. He spent 12 years on the North Side and was a two-time Gold Glove winner and six-time All Star. In his 1,648 games as a Cub he collected 1,619 hits and scored 769 runs. To this day he ranks second behind “Mr. Cub” Ernie Banks in hits, games played and runs scored by a Cubs shortstop.

After the 1975 season, the longtime Cubs shortstop was traded to the Cardinals for Mike Garman and a PTBNL. He was the last player from the famous 1969 team to go.

On May 25, 1976, Kessinger returned to Wrigley Field as a Cardinal. The Cardinals defeated the Cubs 5-2 with Kessinger going 0-for-4 with a walk. Worth noting that he faced his former team on Opening Day as the Cubs opened the 1976 season in St. Louis.

Kessinger would play in 204 games in Cardinals red from 1976 and part of 1977 before being dealt to the White Sox. He hit .239/.318/.303 in St. Louis with one home run and 47 RBI.

The Cardinals did not go anywhere while Kessinger was around and was a pretty forgettable stint for him. His playing success was virtually all with the Cubs, while having a solid go in 1978 with the Sox.

Chicago Cubs: Controversial pitcher spent more time in Chicago than St. Louis

One of the most dominant pitchers of the 1910s and 1920s was right-handed hurler Grover Cleveland “Pete” Alexander. After spending his first seven MLB seasons with the Philadelphia Phillies, Alexander spent the next eight with the Cubs. As a Cub, he pitched to a 2.84 ERA, 1.2 WHIP, 3.08 FIP and struck out 614 hitters in 242 games from 1918 through early 1926.

Because of Alexander’s personal issues, including excessive drinking and insubordination, he was sold to the Cardinals. Cubs manager Joe McCarthy had enough of him despite the ERA titles and Triple Crowns he was winning with his arm.

Alexander joined the ’26 Cardinals team and helped lead them to a World Series championship. He pitched to a 1.33 ERA in the World Series as they defeated the New York Yankees in seven games. It was Alexander who closed out the Cardinals 3-2 win in Game 7. Alexander would stick with the Cardinals through 1929 and pitch to a 3.08 ERA and 1.2 WHIP.

Fans in Chicago might remember him as a Cub, but others might remember his triumph in the 1926 World Series as a Cardinal more than anything. He is certainly not the only Cub to end up joining the Cardinals and winning a ring.

Chicago Cubs: The master of the split-finger is beloved in Chicago and St. Louis

Hall of Fame reliever Bruce Sutter began his career as a Cub in 1976. Over the next five years he would establish himself as one of the best relievers in baseball, using his masterful splitter. The ball would be going straight for the strikezone and then at the very last second drop like a rock. As a Cub he pitched to a 2.39 ERA, 2.32 FIP, 1.1 WHIP and recorded 133 saves. He was also a four-time All-Star.

In December, 1980 Sutter was dealt to the Cardinals in a trade that would include Leon Durham coming to Chicago. While Durham was a very solid player for the North Siders, it was hard for Cubs fans to watch Sutter dominate in St. Louis for the next for years, including winning the 1982 World Series over the Milwaukee Brewers. Sutter pitched to a 2.72 ERA in 249 games as a Cardinal and recorded 127 saves.

While he pitched at Wrigley as a Cardinal in numerous occasions, probably his most notable outing at Wrigley in red was on June 23, 1984. Ryne Sandberg put his name on the map that day when he hit two game-tying home runs off the former Cub reliever in a wild 12-11 win in what is famously known as the “Sandberg Game” today.

Sutter spent nearly an equal time between the Cubs and Cardinals. His 1982 World Series win probably helped him gain more recognition as a Cardinal, but he overall pitched his best with the Cubs and he mastered his craft in Chicago.

Other notable Cub favorites would suit up in Cardinals red, including 2016 World Series champion Dexter Fowler. However, he ended up spending more time in St. Louis than he did in Chicago. There are also players like Ryan Theriot, who for a while was liked as a Cub, but lost a lot of North Side Love when he said he was on the “right side” of the rivalry when he joined St. Louis.