Ross is the 39-year-old backup catcher and father figure of the Cubs who is retiring after the season. Roberts is the 44-year-old rookie manager of the Dodgers. But 14 years ago, their careers intersected as teammates for three seasons with the Dodgers.
When the Dodgers advanced with an unforgettable win Sunday night in Washington, Ross texted congratulations to his former teammate.
"Everybody's got a way -- the 'Cardinal Way,' the 'Dodger Way.' I just like the winning way, whatever that is," said Ross. "I came up with the Dodgers, and there was a style of baseball. I think the West Coast style may be a little more different than other divisions I've been in, to be honest with you. It's more traditional baseball, but you saw the other night, Dave Roberts went outside the box."
The clubs are also connected by Cubs manager Joe Maddon and Dodgers president of baseball operations Andrew Friedman, who worked closely together in Tampa Bay before leaving two years ago for their current roles.
On the coaching staff, Mike Borzello is the Cubs' catching coach of five years after serving as the Dodgers' bullpen catcher for four years, when he was instrumental in the development of closer Kenley Jansen.
On the broadcast side, former Dodgers general manager Ned Colletti, who is now a part of the SportsNet LA broadcast team, grew up in Chicago and worked with the Cubs for 12 years in baseball operations and publicity.
In the front office, Greg Maddux, who began his Hall of Fame career with the Cubs, is a special assistant for the Dodgers.
There even is a Chicago tie at the very top of the Dodgers, as chairman Mark Walter attended Northwestern, lives in Chicago, where his Guggenheim Partners, is based and is a longtime Cubs season-ticket holder.
Ken Gurnick is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.