David Ross Has No Second Thoughts About Coming Home for the 2016 Cubs Reunion

There is a specific kind of gravity attached to October 2016 in Chicago, a pull that even sudden front-office changes and the passage of ten full years cannot dilute. When David Ross walked back into Wrigley Field for the 2016 championship team’s 10-year anniversary celebration on July 18, 2026, he did so without hesitation. It was an appearance preceded by private moments of doubt—moments when the former catcher and manager admitted he briefly wrestled with whether to immerse himself back into an organization that handed him his walking papers in November 2023.

And yet, when the weekend arrived, the choice was simple. You know why? Ross asked. Because my brothers were doing it, and I wanted to be a part of them.

The bond forged during that historic postseason run—when the Cubs outlasted the Cleveland Indians in a seven-game classic to shatter a 108-year championship drought—remains the anchor for much of Ross's post-playing life. Alongside retired first baseman Anthony Rizzo, Ross launched the podcast The Lovable Reunion through Colin Cowherd’s The Volume network in March 2026. The project serves as an extended, long-form victory lap, bringing figures like Joe Maddon, Jon Lester, Theo Epstein, and Kris Bryant back into the fold to dissect the anatomy of a cursed franchise turning the corner.

For Ross, the journey back to Wrigley has been episodic. Following his dismissal by Cubs President of Baseball Operations Jed Hoyer in late 2023—a sudden move that cleared the way for Craig Counsell’s five-year, $40 million contract—Ross spent time reconciling the abrupt end to his four-year managerial tenure. He finished with a 262-284 record, guiding the team to its lone playoff appearance in the pandemic-shortened 2020 campaign. He admitted that the initial sting sent him spiraling into what he calls "Negative Town," caught between rooting for the core players he coached and grappling with the shock of being replaced.

Time, broadcasting gigs with ESPN, and a stint as the Team USA bullpen coach during the 2026 World Baseball Classic have helped clear the air. While no major league teams have called to offer him another managerial post across nearly a dozen recent openings—a reality he accepts as standard baseball commerce—Ross has found comfort in curation. Recording episodes with Rizzo at spots like Murphy's Bleachers and taking the show live to the Chicago Theatre has allowed the old teammates to pull back the curtain on legendary clubhouse moments, from Rizzo's naked, Rocky-inspired speeches to Jason Heyward’s emotional Game 7 rain delay intervention.

When the 2016 team gathered on the field at Wrigley Field in mid-July, the noise of front-office transitions faded. The injuries plaguing the current pitching staff and the offensive slumps of the modern roster belonged to a different era of Cubs baseball. For one weekend, the focus returned entirely to the lunch-pail professionalism, the veteran grittiness of Jon Lester and Ross himself, and a group of players who brought a championship back to the North Side.

This city is great to me, the fans, Ross noted. It’ll be fun to be back in Wrigley and see a packed house and be on that field. I definitely miss that.