5 totally random players you forgot played for both the Cubs and Yankees

As the Chicago Cubs head to the Bronx to close out the first half of the 2025 campaign, Craig Counsell's club will look to vanquish the organization's longstanding demons at Yankee Stadium.

Through the generations, many notable players have called both the Big Apple and Windy City home. More than 200 players have donned the uniforms of both the New York Yankees and the Cubs, including names like Anthony Rizzo, Kerry Wood, Rick Reuschel and Frank Chance, among many others.

But what about some totally random ones? Let's take a crack at five completely forgotten names who've played on both sides of this matchup.

5 totally random players you forgot played for both the Cubs and Yankees

Tony Womack

Tony Womack, at least for me, is best remembered as the second baseman for the 2001 World Series champion Arizona Diamondbacks. In my childhood and even my teenage years, I always looked at Womack as a solid little ballplayer. Stole some bags, caused some chaos - what's not to like?

Spoiler alert: metrics did not love Womack's body of work. Despite swiping 363 bags (T-100 all-time), he finished his 13-year MLB career at 2.5 bWAR/1.6fWAR.

Regardless, the Danville, Virginia native checks the box, having played for both the Cubs and Yankees. He actually played for Chicago twice, closing out the 2003 season with the club - his third team of the season - and came back to close out his career in 2006. Despite having two separate stints on the North Side, he appeared in just 40 games during the Cubs' portion of his career.

Sandwiched in between those runs in Chicago was a year in New York in 2005, which happens to be the worst season of his career if you go by WAR (-2.2bWAR/-2.3fWAR). It's safe to say he's not getting a statue outside either ballpark.

David Phelps

Another name in the long list of mid-tier relievers who had a cup of coffee with the Cubs under Jed Hoyer or Theo Epstein, right-hander David Phelps actually started his career as a member of the New York Yankees.

He made his big-league debut in 2012 as a 25-year-old and, by some measures, it wound up being the best season of his 10-year MLB career. Phelps did a little bit of everything for the Yankees that year, making 33 appearances, including 11 starts and finishing five games, pitching to a 3.34 ERA across 99 2/3 innings of work.

Traded four times in his career, Phelps went from New York to Miami, then Seattle and Toronto before stopping in Chicago in 2019 after being acquired from the Blue Jays. He was a solid arm for Joe Maddon down the stretch, working to a better-than-expected 3.18 ERA (almost every other metric suggested a good deal of luck in that number) - but he got the job done.

Jerry Hairston

Jerry Hairston. 16-year big-league veteran. Very solid Immaculate Grid answer.

A third-generation pro ballplayer, Hairston played for nine teams during his career, spending the bulk of that time (seven years) with the Baltimore Orioles, who drafted him in the 11th round of the 1997 MLB Draft. While he may be a random name, how he wound up with the Chicago Cubs is noteworthy.

Hairston, along with prospects Mike Fontenot and David Crouthers, came back in the trade that sent franchise icon Sammy Sosa to the Orioles ahead of the 2005 campaign, ending the slugger's 13-year run with the Cubs. He didn't exactly 'wow' anyone that year, with his value coming mostly from the fact he played all three outfield positions and second base.

An already sub-par bat got even worse (27 OPS+) in 2006, and the Cubs traded him to Texas for 35-year-old Phil Nevin. Three years later, he went from Cincinnati to the Bronx in a deadline deal. And, if you know your baseball history, you know the Yankees won the World Series that year. So the journeyman has a ring in his trophy case at home, thanks to his 45 regular-season games with New York that summer.

Chad Gaudin

Drafted in the 34th round of the 2001 MLB Draft out of high school, Chad Gaudin bounced around the league for a little more than a decade, spending more than one year with just two of the nine teams he pitched for.

Similar to Hairston, his Cubs' tenure came to be thanks to a memorable trade. Acquired in the deal that brought Rich Harden to Chicago and sent Josh Donaldson and a trio of other players to the A's in return, Gaudin struggled down the stretch, with an ERA north of 6.00. Chicago cut him loose the following spring and he signed with San Diego.

That August, he joined the Yankees - and he was Hairston's teammate as New York won its first championship since 2000. Another random Cubs-Yankees connection with some title hardware.

Cameron Maybin

The tenth overall pick in the 2005 MLB Draft by the Tigers, Cameron Maybin is one of the rare first-rounders who barely spent any time with the club that drafted him - yet still had a lengthy, respectable career.

Maybin was part of the blockbuster between the Tigers and Marlins in Dec. 2007 that sent Miguel Cabrera and Dontrelle Willis to South Florida. Cabrera went on to put together a career that will soon culminate in a plaque in Cooperstown. That marked the first of many moves Maybin would make in his 15-year career that saw him play for one-third of the league.

He played for the Yankees in 2019 and was a shockingly solid contributor for Aaron Boone's club, posting a 1.6 bWAR and 127 OPS+ in just 82 games. His time in a Cubs uniform came that very next year, the COVID-shortened 2020 campaign - hence why many folks don't even remember he played for Chicago.