Presented By Cubs Insiders

With Tom Brady leaving New England, it got us wondering: Which Cubs player was it strangest to see don another club’s uniform?

The question probably poked at some sore spots for fans, but we posed it to Cubs Twitter anyway. Here’s what you all had to say:

Ron Santo — White Sox (1974)

Billy Williams — A’s (1975-76)

Man, seeing these two Cubs Hall of Famers in other jerseys is so wrong. 

Fergie Jenkins — Rangers (1974-75, 1978-81) and Red Sox (1976-77)
Andre Dawson — Marlins (1993-94) and Red Sox (1995-96)

Jenkins spent the first two seasons of his career with the Phillies but made a name for himself on the North Side. He rejoined the Cubs before retirement (1982-83).

While Jenkins’ Hall of Fame hat depicts him with a Cubs hat, Dawson’s (Expos) does not. The Hawk spent 11 seasons with Montreal (1976-86), so we’ll give him a pass. He won his lone MVP award (1987) on the North Side, though.

Greg Maddux — Braves (1993-2003), Dodgers (2006, 2008) Padres (2007-08)

I don’t have to remind you about Maddux’s departure from Chicago, right? Okay, good. At least he came back 12 seasons later?

Ryne Sandberg — Philies (1981 as player, 2013-15 as manager)

Remember when Sandberg was a Cubs managerial candidate?

Mark Grace — Diamondbacks (2001-03)

Grace won the World Series with Arizona in 2001, you guys. Good for him.

Rick Sutcliffe — Orioles (1992-93) and Cardinals (1994)
Bruce Sutter—Cardinals (1981-84) and Braves (1985-88)



Sutcliffe pitched for the Dodgers (1976-81) and Indians (1982-84) before joining the Cubs in 1984. We assume the weirdness stems from his time in St. Louis, Toby? And the same goes for you with Sutter, David?

Shawon Dunston

Dunston played for five teams in the six seasons he wasn’t a Cub, including two stints with the Giants (1996, 1998).

Sammy Sosa — Orioles (2005) and Rangers (2007)

Google “Sammy Sosa Orioles.”  THAT is a weird sight.

Kerry Wood — Indians (2009-10) and Yankees (2010)


Why did the Cubs ever let Wood walk in free agency? They brought him back in 2011, not before he donned a Yankees jersey (*shivers*).

Derrek Lee — Braves (2010), Orioles and Pirates (2011)

As Mike points out, the Cubs literally traded Lee to Atlanta and squared off at Wrigley Field two days later. Awkward.

Some other 2000s Cubs:

Carlos Zambrano — Marlins (2012)

Aramis Ramirez — Brewers (2012-15) and Pirates (2015)

Ryan Theriot — Dodgers (2010), Cardinals (2011) and Giants (2012)

Kosuke Fukudome — Indians (2011) and White Sox (2012)

And some more recent Cubs:

Starlin Castro — Yankees (2016-17), Marlins (2018-19) and Nationals (present)

Dexter Fowler — Cardinals (2017-present)

Jake Arrieta — Phillies (2018-present)

Pedro Strop — Reds (present)

Nick Castellanos — Reds (present)

Joe Maddon — Angels (present)

And, finally,  Jim’s got jokes.

Eloy Jimenez (2019-present)

Any names come to mind not on this list? 

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