Overview of The Lovable Reunion - Tom Ricketts on breaking Chicago Cubs curse, World Series rain delay & celebration | Ross & Rizzo
This episode of The Lovable Reunion is a warm, story-filled conversation between Anthony Rizzo, David Ross, and Cubs chairman Tom Ricketts about the rise of the 2016 Chicago Cubs. Ricketts reflects on growing up a Cubs fan, buying the team with his family, rebuilding Wrigley and the organization, hiring Theo Epstein and Joe Maddon, and the emotional payoff of winning the World Series. The tone is nostalgic, funny, and personal, with plenty of behind-the-scenes details about the clubhouse, team culture, and the celebration that followed the title.
Key Topics Discussed
Tom Ricketts’ Cubs origin story
- Grew up in Omaha with a normal, modest upbringing.
- Became a Cubs fan after falling in love with the 1984 team and Wrigley Field.
- Used to spend weekends at Wrigley, often sitting in the center-field bleachers.
- Even met his wife there, making the Cubs part of his family history before he ever owned the team.
Buying the Cubs and the family decision
- Ricketts explains how he approached his father and siblings about using family money to help buy the team.
- His father initially called it “the stupidest thing” he’d ever heard.
- After seeing Wrigley firsthand from the rooftops and in the neighborhood, his family understood the opportunity and got on board.
Rebuilding the organization
- Ricketts describes the long list of structural issues the team had to fix:
- Wrigley renovations
- Spring training upgrades in Mesa
- Dominican Republic facilities
- Clubhouse and player amenities
- More bathrooms, better exits, improved fan experience
- He says the goal was to make the Cubs a first-class organization on and off the field.
Hiring Theo Epstein
- Ricketts talks about a secret, wide-ranging search that ultimately led him to Theo.
- Theo emphasized that success is built by a team, not one person.
- Ricketts praises Theo’s mix of baseball knowledge, communication skills, and emotional intelligence.
Building the championship culture
- The episode emphasizes the shift from “lovable losers” to expected winners.
- Ricketts, Theo, Joe Maddon, and the players all helped create a more open, accountable, and fun environment.
- Charity work, community involvement, and team bonding were major parts of the culture.
Joe Maddon’s impact
- Ricketts credits Joe with keeping the clubhouse loose and not feeding into the “curse” narrative.
- He believes Joe’s personality and media handling helped reduce pressure and distractions.
- The result was a team that played with confidence and identity.
Memorable 2016 Championship Moments
The path to the title
- Ricketts recalls the team’s rise through 2014 and 2015 as the point when the Cubs stopped feeling like underdogs.
- Key additions like Jon Lester, Ben Zobrist, Jason Heyward, and David Ross helped solidify the roster.
- He highlights the 2015 wild card win over Pittsburgh as a major turning point.
World Series rain delay and Game 7 stress
- Ricketts says the Game 7 rain delay in Cleveland was one of the most stressful moments of his life.
- He was terrified the title might slip away after all the work to get there.
- He recounts the emotional, almost surreal feeling of watching the ninth inning unfold and not wanting to jinx anything.
The parade and celebration
- The parade down Addison and the rally in Grant Park are described as overwhelming and unforgettable.
- Ricketts says he spent a lot of the day managing logistics for family and friends so everyone could be part of it.
- He views the celebration as a gift to the fans and the city.
Notable Anecdotes
The last out ball
- Anthony Rizzo reveals he has the final out ball from Game 7 in his possession.
- He explains that the plan was always to give it back to Ricketts.
- Rizzo says he was once told the ball had already been offered for $2 million.
- Ultimately, he hands it over, saying it belongs with the Cubs and their history.
Ricketts’ hands-on fan approach
- He explains that he still walks through the ballpark, hands out baseballs, and talks to fans.
- He intentionally avoids being a distant “owner in a suite.”
- Players say that accessibility mattered, especially for the younger team trying to grow without pressure.
Family and baseball
- The conversation repeatedly returns to how much the Cubs became a family project:
- Ricketts’ family invested together
- His wife and kids are part of the Wrigley experience
- Players and staff were treated like family too
Main Takeaways
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The Cubs’ 2016 title was built over years, not one season. The championship came after major infrastructure work, roster construction, and cultural changes.
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Leadership style mattered as much as talent. Ricketts, Theo Epstein, Joe Maddon, and the players all helped create a calm, collaborative environment.
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Ricketts sees himself as a fan first. His decisions were shaped by what he wished the team and ballpark would feel like from a fan’s perspective.
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The title meant more because of the history. Breaking the curse, winning at Wrigley, and celebrating with fans made the moment especially emotional.
Bottom Line
This episode is part victory lap, part behind-the-scenes ownership story, and part love letter to Cubs fans. Tom Ricketts comes across as deeply sincere, nostalgic, and proud—not just of winning a championship, but of helping transform the Cubs into a modern organization rooted in family, community, and belief.