5) Paul Maholm
Did you know that Paul Maholm was a first-round pick of the Pittsburgh Pirates out of Mississippi State? Well now you do. The left-hander spent seven years with the team that drafted him, from 2005 to 2011, making 185 starts in a Pirates uniform and pitching to a 4.36 ERA.
The Cubs brought him in ahead of the 2012 season, intimately familiar with his reliable middle-of-the-rotation arsenal, and got their money's worth: 2.0 bWAR and 120+ innings of work in half a season before flipping him to the Atlanta Braves along with outfielder Reed Johnson (what I wouldn't give for a Reed Johnson coming off the Cubs' bench today) in exchange for Arodys Vizcaino and Jaye Chapman.
Not a head-turning pitcher by any stretch, but he definitely checks the box, especially in Chicago, as a forgotten name that called both cities home during his 10-year big-league career.
