Everything about the way David Ross left the Chicago Cubs felt wrong. It was abrupt. It was cold. It was, in many ways, the polar opposite of the warm, fuzzy "Grandpa Rossy" narrative we’d all bought into for years. One minute, he’s the fiery leader getting an extension; the next, he’s out of a job because the front office found a "shinier" toy in Craig Counsell.
But if you only look at how it ended, you're missing the point.
David Ross wasn't just another name on the managerial carousel. He was a bridge. He represented the soul of a franchise that spent a century figuring out how to lose and then, suddenly, forgot how to fail. Honestly, to understand why people still get fired up about David Ross Chicago Cubs trivia or his managerial record, you have to go back to 2016. Or maybe even further.
The Catcher Who Refused to Go Away
Let’s be real: David Ross was a journeyman. He played for seven different teams. He was a backup. You’ve seen his stats—a career .229 hitter doesn’t usually become a cultural icon. But there was something about the way he handled a pitching staff. He was a "pitcher’s catcher."
When the Cubs signed him to a two-year, $5 million deal in late 2014, it wasn't for his bat. It was for Jon Lester. The two were a package deal, a battery that brought a certain "get off my lawn" toughness to a clubhouse full of kids like Kris Bryant and Anthony Rizzo.
Ross was 39. He was old. He was "Grandpa."
Then came 2016. In the most high-stakes game in the history of the sport—Game 7 of the World Series—Ross did the unthinkable. He hit a solo home run off Andrew Miller. At 39 years old, he became the oldest player to ever homer in a World Series Game 7. You can’t make that stuff up. It was his final game. He literally went out on top, carried off the field on the shoulders of his teammates.
Transitioning to the Manager’s Seat
Most guys take their ring and go play golf. Ross stayed. He took a front-office role, did the TV thing on ESPN, and basically waited for the inevitable. When Joe Maddon’s time ran out after 2019, the "Hire Ross" chants were deafening.
The Cubs hired him on October 24, 2019. It felt like destiny.
But management is a different beast than catching. Ross took over a team that was transitioning. The "Golden Era" core was aging or getting too expensive. Then, the world stopped. His first season was the 60-game pandemic sprint in 2020. People forget he actually won the NL Central that year. He went 34-26 and finished third in Manager of the Year voting.
It looked like the Cubs had found their guy for the next decade.
The Gritty Reality of the Managerial Years
The honeymoon didn't last. 2021 was a gut punch. The front office traded away Rizzo, Bryant, and Baez. Ross was left holding the bag for a rebuild he didn't necessarily sign up for.
- 2021: 71-91 (4th in NL Central)
- 2022: 74-88 (3rd in NL Central)
- 2023: 83-79 (2nd in NL Central)
If you look at that 2023 season, the Cubs were this close. They were in the playoff hunt until the final week. Ross had them playing hard. But Jed Hoyer saw an opportunity to grab Craig Counsell from the Brewers, and he didn't hesitate. Ross was fired on November 6, 2023.
It was a business move. It was brutal.
What Most People Get Wrong About the "Ross Era"
Critics love to point at his .480 winning percentage. They say he was too "old school" or that he played favorites with certain veterans. Kinda feels like every manager gets that critique these days, though.
The reality? Ross was a "shield." He took the heat while the organization overhauled the farm system. He managed through a literal pandemic and the fire sale of the most beloved roster in Chicago history. He wasn't just a mascot; he was the guy keeping the clubhouse from imploding when the stars were shipped out for prospects.
Why 2026 is the Year of the Reunion
Fast forward to right now. It’s January 2026. After a couple of years of silence and some well-deserved time away, the David Ross Chicago Cubs connection is finally healing.
It was recently announced that Ross will attend the Cubs Convention this month. It’s for a 10-year anniversary celebration of that 2016 team. This is huge. For a while, it seemed like the bridge was burned. There was genuine hurt there. But fans are ready to give him that standing ovation he never really got as a manager.
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He’s also keeping busy on the national stage. Ross is serving as a bullpen coach for the 2026 World Baseball Classic. He still has that "itch." You can see it in his eyes when he talks about the game. Whether he ever manages in the big leagues again is a toss-up, but his impact on the North Side isn't going anywhere.
Takeaways for the Die-Hard Fan
If you’re still wearing your #3 Ross jersey to Wrigley, don't feel like a dinosaur. Ross represents a specific type of leadership that’s becoming rare in the era of "manager-by-algorithm."
- Culture over Analytics: While the game is dominated by data, Ross proved that "vibes" and veteran leadership actually matter in a 162-game grind.
- The "Lester Effect": Ross showed that a backup catcher can be more valuable than a starting shortstop if he knows how to handle a pitching staff.
- Grace in Defeat: Despite the way he was dumped, Ross hasn't spent the last two years trashing the organization. That says more about his character than a win-loss record ever could.
The David Ross Chicago Cubs story is one of the most unique in sports. It's a tale of a guy who was never supposed to be the hero, became one anyway, and then had to navigate the messy reality of being the boss.
If you're heading to the Cubs Convention this year, expect it to be emotional. He’s coming home, even if home looks a little different than it did in 2016. It’s about time.
Actionable Insights for Fans
- Watch the 2016 Documentary: If you haven't seen "The 2016 World Series" film recently, go back and watch the Ross highlights. It reminds you why he was the heart of that team.
- Check the WBC Schedule: Follow Team USA in the upcoming World Baseball Classic to see Ross back in uniform and in the dugout.
- Support the Foundation: Keep an eye on the charity work Ross continues to do in the Chicago area; his commitment to the city didn't end with his contract.