Watch: Jon Lester Tells Story of Bringing David Ross to Chicago
I’ve heard mixed reviews on The Lovable Reunion podcast with Anthony Rizzo and David Ross, but I might have to dive in for myself after watching this snippet from their conversation with Jon Lester. In it, the venerable lefty tells the story about how he convinced Theo Epstein to sign Ross as a backup catcher while out celebrating his recent deal with the Cubs.
The best part of this story by a wide margin is Epstein negotiating with just hand signals while drinking a beer at 2am. Very strong Jake Taylor vibes from Ross as well. Does everyone else remember when the Cubs were fun? Man, those were the days.
A night at Bub City, 7 missed phone calls at 2 a.m., Theo Epstein making a signing mid-beer.
The story of David Ross’ Chicago Cubs negotiation is truly an ALL-TIMER ?? pic.twitter.com/1STnDE1TF1
— Lovable Reunion (@LovableReunion) April 7, 2026
