The rivalry between the Cardinals and the Cubs is more deep-seated than its novelty has to be stated. The Lou and the Windy City hold a special place in each other’s hearts in that the space is rather void of positivity. Some all-time great games, matchups and moments have been born when these two squads square off. Those who make a name in their opponents’ city usually do so for how they fared in these quarrels.

A select group of the thousands who have put on a big league jersey at any point can say they toed each side of the rivalry rubber.

• 130 years in, Cards-Cubs rivalry still fierce | Top moments of Cards-Cubs

Hall of Famers, club legends and postseason greats have sported both Cubbie blue and the birds on the bat at different points in their career. 

Catcher Willson Contreras is set to become the latest to make the jump from one side to another in this rivalry. The longtime Cubs backstop reached a five-year deal in free agency with the Cardinals (per a source) at the 2022 Winter Meetings, as St. Louis opted to make Contreras its replacement behind the plate for franchise icon Yadier Molina, who retired at the end of the 2022 season.

More than 350 players have played for both the Cubs and Cards, and only 34 can say they spent their careers split only between the two teams.

For purposes of this list, we’re picking some of the highlights, whether they be enshrined in the Hall of Fame, are notable players from one team who might surprise you to have played on the other or are recent examples of crossing the rivalry line. (The full lineup comes courtesy of Baseball-Reference’s multifranchise search function.)

Lou Brock: Far and away the top trade in Cardinals history, Brock’s career accomplishments and lore in baseball history have him as perhaps the most notable name on this list. His trade from Chicago to St. Louis was from a time where swaps between these two franchises were more plentiful. He is one of the few who appeared only for the Cubs and Cards in his career.

Bruce Sutter: Far and away the best years of Sutter’s Hall of Fame career came as both a Cub and a Cardinal, winning the Cy Young with Chicago in 1979. But it was in St. Louis where he captured that elusive World Series crown, having his number retired by the club in 2006 and entering Cooperstown with a Cardinal cap.

Lee Smith: Another impactful, Hall of Fame closer, Smith was at his peak when he was donning either Cubbie blue or Cardinal red. Unlike Sutter, though, Smith added a laundry list of teams to his resume before he called his playing days over.

Rogers Hornsby: Perhaps the greatest player on this list, Hornsby was an MVP and player-manager for both clubs. The Hall of Famer won his only World Series and his two Triple Crowns as a Cardinal.

Dizzy Dean: The Hall of Famer was a workhorse and MVP for the Cards before spending his next four years with Chicago, never replicating the same success.

Daniel Descalso: Here’s one of the contemporary variety. Descalso was a World Series champ with St. Louis in 2011 before playing a single year for the Cubs in 2019, after which he retired from playing.

Hank Sauer: “The Honker” was the MVP in 1953 as part of his seven years in Chicago, spending one mostly stunted campaign for the Cards in 1956, at the age of 39.

Dennis Eckersley: Hopping back onto the Hall of Fame closer train, Eckersley’s most memorable days came well removed from when he was a Cub and played through the twilight of his career with St. Louis. But he remains a double-dipper in this rivalry nonetheless.

Jason Motte: What’s another closer? The owner of the last pitch in the Cards’ 2011 World Series triumph traded the birds on the bat for Cubbie blue as a free agent before the 2015 season -- the only season he would compete as a Cub.

Rick Sutcliffe: The association game pinpoints Sutcliffe with the Cubs as soon as his name is mentioned, etching his way into Chicago lore as soon as he landed with the club in June 1984. But do you recall that he played a season in St. Louis in 1994?

Jon Lester: It was a stark visual to see Lester, just a half-season removed from being a Cub, traded to the Cardinals at the 2021 Trade Deadline. Despite it, he’ll go down as a memorable Cub and Red Sox, a champion with both.

Jim Edmonds: The star center fielder played only 85 games for the Cubs after he was released by the Padres in the middle of the 2008 season. That does little to diminish his place in Cards fans’ hearts, now calling games for Bally Sports Midwest.

Mordecai Brown: “Three Finger Brown” was a legend across 10 seasons for the Cubs, but did you know his first year in the league was as a Cardinal?

Lon Warneke: Paralleling Brock on the pitching side, Warneke owns the most appearances to have played for only these two franchises. He captured the ERA title as a Cub in 1932 -- finishing second for MVP -- and split his career via 10 seasons with Chicago, six with St. Louis.

Ernie Broglio: Broglio might be the better-known arm to have spent his entire career between these two franchises, due in part to his place in the lopsided trade that send Brock to St. Louis.

Dexter Fowler: Is one of the more recent examples to have switched rivalry sides in back-to-back years. Jason Heyward did the same but transferred from St. Louis to Chicago.

José Cardenal: His best days came by and large with the Cubs, for whom he spent six seasons. But who knows what kind of legend he could have become if Carednal was a Cardinal for more than parts of just two seasons?

Ryan Theriot: A popular Cubs infielder who found postseason glory on the 2011 Cards team, Theriot added fuel to the rivalry fire when he said he’s on “the right side of the rivalry” after signing with St. Louis.

Jaime García: One of the more successful lefties in recent Cards history, Garcia was a favorite in St. Louis before ultimately appearing in just eight games as a Cub, throwing his last big league pitch for them in 2018.

Joe Girardi: On the flipside of Garcia, Girardi’s playing days are more closely tied to Chicago, but he finished his playing career with the Cardinals in 2003. He’s gone on to bigger things as a manager.

Ripper Collins: Part of the legendary Gashouse Gang, Collins was sent to Chicago as part of the trade that brought Warneke to St. Louis.

Don Kessinger: A six-time All-Star for Chicago, Kessinger spent the most time of any individual on this list (1,648) to have later played as a Cardinal, making 204 appearances as a Redbird.

Hoyt Wilhelm: The Hall of Famer spent parts of just two seasons playing for Chicago or St. Louis as part of his 21-year career. Jamie Moyer follows a similar path, breaking into the league as a Chicago draftee and spending one season in St. Louis but is better known for his time elsewhere.

Ken Reitz: The late “Zamboni” was a Cardinal mainstay in the 1970s before spending one season with the Cubs.

Jon Jay: Like Descalso, Jay was another Cardinal favorite and champion from 2011 who later continued his career with the Cubs.

Non-player division: “The Fordham Flash” was a Hall of Fame player-manager for the Cards, but Frankie Frisch also commandeered the Cubs as manager well after his playing days were over, as did Roger Bresnahan, who was player-manager for Chicago his last year in the Majors in 1915. … Tony La Russa played a single game for the Cubs in 1973 before steering the Cards to a pair of World Series titles in the 21st century. … Legendary broadcaster Harry Caray spent over two decades calling Cardinals games before he took over his more memorable role as the play-by-play voice of the Cubs … Did you know Bob Costas’ first break came calling basketball on the KMOX airwaves in St. Louis and at Mizzou before he became central in the Chicago media market?