10 Baseball Players who Played for Cubs and Red Sox
There is a good chance that if you’ve found this page then you’re playing the Immaculate Grid.
That also means that today’s grid has asked for players that have played for both the Chicago Cubs and Boston Red Sox.
And, it also means that you’re probably stuck on this particular box and you’re looking for a little help. Sound about right so far?
Well, good news, you’re in the right place.
I’ve done some research and have found players who played for both the Cubs and Red Sox.
Popular Choices
Jon Lester
Jon Lester was a powerhouse pitcher in baseball from 2006 until 2021. He’s thrown for the Red Sox, Cubs, Nationals, Cardinals and Athletics. Lester was a part of the Red Sox’s World Series wins in ’07 and ’13, and also helped the Cubs break their 108-year championship drought in 2016.
He finished his career with exactly 200 wins and struck out more than 2,400 batters. Lester was also a 5-time All-Star and NLCS MVP.
*Lester was the most popular pick for this square in a previous grid (Grid 98).
Nomar Garciaparra
Nomar Garciaparra is best known for his time with the Boston Red Sox, where he was a key figure in the team’s success in the late 1990s and early 2000s.
Garciaparra had an immediate impact in the league, winning the American League Rookie of the Year award in 1997. Known for his unique batting stance and exceptional hitting abilities, he won two consecutive batting titles in 1999 and 2000, hitting .357 and .372 respectively.
He was a six-time All-Star and a consistent offensive force, achieving a .313 career batting average with 229 home runs. In addition to the Red Sox, he also played for the Cubs, Dodgers, and Athletics.
Garciaparra Key Stats
- Rookie of the Year (Red Sox)
- All-Star (Red Sox, Dodgers)
- Silver Slugger (Red Sox)
- .300+ Career Average (Red Sox, Dodgers, Cubs, Athletics)
- 200+ Hits Season (Red Sox)
- 100+ RBI Season (Red Sox)
- .300 Batting Average Season (Red Sox, Dodgers)
Craig Kimbrel
Craig Kimbrel made his MLB debut with the Atlanta Braves in 2010, quickly earning the closer role. In his rookie season, he recorded 46 saves, a 2.10 ERA, and was named the NL Rookie of the Year. He went on to lead the National League in saves for four consecutive seasons from 2011 to 2014, earning All-Star honors in each of those years.
After his time with the Braves, Kimbrel played for the San Diego Padres before being traded to the Boston Red Sox. He continued to be one of the league’s best closers, helping the Red Sox win the World Series in 2018 with some crucial postseason performances.
Kimbrel’s later career has included stints with the Cubs, White Sox, Dodgers and Phillies. His ability to strike out batters at a high rate and close out games with efficiency has been a hallmark of his career.
Kimbrel Key Stats
- All-Star (Braves, Red Sox, Cubs, Phillies)
- World Series Champ (Red Sox)
- 300+ Career Saves (Braves, Red Sox, Cubs, Phillies, Dodgers, Padres, White Sox)
- 40+ Save Season (Braves, Red Sox)
Rare Choices
Kyle Schwarber
Kyle Schwarber is a left-handed hitting slugger who primarily plays as a left fielder and designated hitter. He debuted in the MLB in 2015 with the Chicago Cubs. Schwarber is known for his power at the plate, with career highlights including a .480 slugging percentage through the 2022 season.
He had a memorable 2015 postseason, belting five home runs in just nine games. However, he suffered a significant knee injury early in the 2016 season but made a dramatic return during the World Series the same year, helping the Cubs to their first championship in over a century.
Schwarber has since played for the Nationals, Red Sox and Phillies, continuing to add to his career totals of over 225 home runs and 500 RBIs.
Schwarber Key Stats
- All-Star (Nationals, Phillies)
- Silver Slugger (Phillies)
- 40+ Home Run Season (Phillies)
John Lackey
John Lackey, a right-handed pitcher, carved out a strong MLB career from 2002 to 2017, primarily with the Los Angeles Angels, Boston Red Sox, and Chicago Cubs. Over his career, Lackey recorded 188 wins with a 3.92 ERA and 2294 strikeouts.
He was an All-Star in 2007 (Angels) and was known for his tough, competitive approach on the mound. Lackey achieved rare success in the postseason, winning World Series titles with the Angels (2002), Red Sox (2013), and Cubs (2016).
In fact, he became the first pitcher in history to start and win the clinching game of a World Series as a rookie with the Angels in 2002.
Heathcliff Slocumb
You may remember Heathcliff Slocumb as a relief pitcher with the Phillies and Red Sox in the 90s, but he was a bit of a journeyman playing for 8 teams over the course of 10 years. (Cubs, Phillies, Cardinals, Red Sox, Mariners, Padres, Indians (now Guardians), Orioles)
He was a solid reliever with some good seasons and even an all-star appearance while with the Phillies in 1995.
However, he might be best known in baseball lore for being traded from the Red Sox to the Mariners in 1997 for Derek Lowe and Jason Varitek, a deal that later appeared very lopsided in Boston’s favor.
Jamie Moyer
Jamie Moyer was a steady pitcher in baseball for an impressive stretch from 1986 to 2012. He made a name for himself with teams like the Mariners and Phillies, but also had stops with the Cubs, Orioles, Rangers, Rockies, Cardinals and Red Sox.
Over his career, he snagged over 260 wins, proving that you don’t need a blazing fastball to get the job done. Moyer was an All-Star once and was also a big part of the Phillies’ World Series win in 2008.
What’s really cool about him is that he pitched in the majors until he was 49, which is just amazing.
Rick Aguilera
Rick Aguilera had a solid 16 year career, best known for his time as a relief pitcher with the Twins. In addition to the Twins, Aguilera also played for the Mets, Cubs and Red Sox.
Transitioning from a starting role to the bullpen, Aguilera amassed over 300 saves in his career including two seasons (’91 and ’92) with over 40. He was a three-time All-Star and consistently among the best closers in the game during his peak.
Matt Stairs
Matt Stairs had a lengthy Major League career that spanned from 1992 to 2011, during which he played for 12 different teams, essentially making him an Immaculate Grid Hall-of-Famer.
Known for his power-hitting abilities, primarily as a pinch-hitter, he hit 265 home runs over his career and holds the record for the most pinch-hit home runs in MLB history with 23. Stairs had a career batting average of .262 with an OPS of .832, and recorded 899 RBIs.
Notably, in the 2008 postseason with the Philadelphia Phillies, he hit one of the most famous home runs in Phillies history, helping the team move onto the World Series that year.
Rich Hill
Rich Hill is an Immaculate Grid beast. The left-handed pitcher has played for 13 different clubs over his incredible 19-year career – one that is still ongoing as I’m writing this (he’s currently pitching with the Padres).
Hill’s MLB journey began when he was drafted by the Chicago Cubs in 2002. After making his major league debut in 2005, he had initial success with the Cubs, particularly in 2007 when he had a standout season. However, injuries, inconsistency, and command issues led to him bouncing around the minors and various MLB teams for several years.
After refining his pitching approach and mechanics, he experienced a career resurgence starting in 2015. At an age when many players see diminished returns, Hill became one of the most effective starters in baseball. This late-career renaissance led to stints with the Red Sox, Athletics, Dodgers, Twins, and Rays.
