Greg Maddux
Maddux is one of those unique players who excelled long enough for two different teams that he is legendary with both.
He came up through the Cubs farm system and made a name for himself on the North Side as a control artist. He left Chicago after winning the Cy Young Award for the Cubs in 1992 and then became a part of the Braves legendary 90s era rotation with John Smoltz and Tom Glavine, winning three more Cy Youngs.
In 2004 though, Cubs fans got to experience déjà vu as Maddux signed as a free agent to come back to Wrigley Field, presumably to help the Cubs make it back to the World Series, which they narrowly missed the year before. While not the Cy Young winner of years past, he would register a 3.2 WAR in ‘04 and 2.9 in ‘05. Maddux still provided some memorable moments, winning his 300th game and notching his 3,000 career strikeout back in Cubbie blue.
Unfortunately, those Cubs teams, while talented and loaded with starting pitching, would fail to make the playoffs, finishing 3rd and 4th, and Maddux was traded by the Cubs during the ’06 season to the Dodgers (another team he would boomerang back to later in his career).