Ten years after the Chicago Cubs finally lifted the World Series trophy and shattered a 108-year championship drought, the legacy of the 2016 team continues to resonate throughout the organization and the city it represents. That legacy extends beyond the long-awaited championship. It reshaped the culture of the franchise. Winning became the expectation.
That shift was front and center this weekend at Cubs Convention, where a large portion of the 2016 roster reunited to kick off a yearlong celebration of the team’s 10-year anniversary. Familiar faces filled the convention space, rekindling the chemistry and energy that defined one of the most significant seasons in franchise history. The reunion will continue into the summer, serving as both a celebration and a reminder of what that group accomplished.
To a man, the players expressed pride in changing the tone around the Cubs and in showing how Chicago responds to champions.
“The kids that are actually getting to the big leagues now, they have that pressure,” former Cubs catcher Miguel Montero said. “They need to win. Now, they walk in and they see us: ‘Those are the guys that won the World Series.’ Yeah, we are. We set the bar really high.”
Several members of the 2016 team participated in a panel during Saturday’s events at Cubs Convention, including Anthony Rizzo, Ben Zobrist, Pedro Strop, Mike Montgomery, Justin Grimm and Montero. More former Cubs were present for Friday night’s opening ceremony, which included the announcement that Jon Lester will be inducted into the Cubs Hall of Fame.
Nearly the entire championship core gathered privately one night earlier at Wrigley Field. Former president of baseball operations Theo Epstein attended along with former manager Joe Maddon. Kyle Schwarber and Javier Báez flew in for the celebration, while David Ross, Jason Heyward, Kyle Hendricks and numerous former players, coaches and staff members were also on hand.
“It was bizarre how quick the same energy showed up with all those same people,” Zobrist said. “The same voices are yapping and going back and forth with each other. And the joy just of the moment returns, and you feel like, it’s the same guys.”
The setting amplified the nostalgia. Jerseys from the 2016 roster lined the clubhouse at Wrigley Field, recreating the atmosphere that fueled that championship run. Montero joked that he was especially pleased to see a bar set up near his locker, a detail that felt fitting for a team known for its clubhouse chemistry.
The drinks and stories flowed late into the night, echoing the celebrations that followed big wins throughout that historic season. Asked about the party, the players leaned into their trademark humor.
“Afternoon tea,” Rizzo quipped.
“It was pretty quiet,” Montero added with a smirk, drawing laughter from the crowd.
Time away has only strengthened the bond among the group. Rizzo reflected on how the decade apart made the reunion feel both meaningful and familiar.
“Ten years away from each other has been the perfect amount of time,” Rizzo said. “For all of us to love each other again. It was honestly like we had just won a playoff series.”
Beyond nostalgia, the reunion underscored the lasting impact the 2016 Cubs have had on the organization. Once defined by heartbreak and mythology, the franchise emerged from that season with a new identity built on belief and accountability. Players entering the Cubs system now do so under the shadow of a championship standard that did not previously exist.
That message remains clear a decade later: winning in Chicago is not a hope — it is the expectation.
The celebration is not finished. The Cubs are planning another tribute to the 2016 team in July at Wrigley Field, and president of business operations Crane Kenney told 670 AM The Score that the organization will unveil a permanent tribute in Gallagher Way honoring the championship group.
“I’ll be pushing for us to be in the bleachers for the reunion weekend,” Rizzo said.
It would be a fitting image — the players who ended generations of heartbreak once again at the heart of Wrigley Field, surrounded by fans who will never forget the season that changed everything.
