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6 Baseball Players who Played for Pirates and Cubs

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 Pittsburgh Pirates and Chicago Cubs.

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 on both the Pirates and the Cubs.

Moises Alou

Moises Alou, who played from 1990 to 2008, is best known for his time as an outfielder with the Montreal Expos, Florida Marlins, and Chicago Cubs.

Over his 17-season career, Alou compiled over 2100 hits, 332 home runs, and a .303 career batting average. He was named an All-Star six times (Expos, Marlins, Astros, Cubs, Giants) and played a key role in the Florida Marlins’ 1997 World Series championship.

His best statistical season might have been in 2000 with the Houston Astros when he hit .355 with 30 home runs and 114 RBIs.

Jason Kendall

Jason Kendall is highly regarded for his role as a catcher in Major League Baseball from 1996 to 2010. He played for the Pittsburgh Pirates, Oakland Athletics, Chicago Cubs, Milwaukee Brewers, and the Kansas City Royals.

A three-time All-Star (Pirates), Kendall had a .288 lifetime batting average (.327 in ’98 with Pittsburgh), 75 home runs, and 744 RBIs. He also accumulated 189 stolen bases, an impressive number for a catcher.

His reputation for toughness and durability resulted in him catching over 2000 games, one of only a few catchers to reach this milestone.

Tony Womack

Tony Womack is known for his career as a second baseman and outfielder in Major League Baseball from 1993 to 2006. Womack’s first stint was with the Pittsburgh Pirates where he played from 1993 to 1998, followed by time with the Diamondbacks, Rockies, Cubs, Cardinals, and Yankees.

Womack had a career batting average of .273 and accumulated 363 stolen bases, making him one of the most dangerous base runners during his time.

Perhaps his most significant contribution was in the 2001 World Series, where his 9th inning hit for the Diamondbacks in Game 7 led to the winning run against the Yankees.

Womack Key Stats

  • All-Star (Pirates)
  • 30+ Stolen Base Season (Pirates, Diamondbacks)
  • .300+ Batting Avg Season (Cardinals)

Benito Santiago

As a young catcher growing up, I remember seeing Benito Santiago throwing players out from his knees and thought it was the coolest thing ever and something I remember imitating in Little League games.

But, that’s not what matters here. What matters is that 5 time All-Star Benito Santiago played for 9 different teams throughout this 20 year career which makes him an absolute force on the Immaculate Grid.

Santiago played for Padres, Giants, Reds, (Florida) Marlins, Blue Jays, Royals, Pirates, Phillies and Cubs.

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.


More Immaculate Grid Guides

Pirates and Braves

Cubs and A’s

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