Chicago Cubs’ 2016 World Series Anniversary: Remembering the Highlights and Challenges

Fans of the Chicago Cubs are marking the 10-year anniversary of the 2016 World Series win. Ten years is a significant milestone, and the Cubs dedicated much of the 2026 season to this event. They created a ceremonial archway at Gallagher Way and invited past players and team staff to join the celebrations. However, a beloved fan tradition from that playoff journey is often overlooked.

In the aftermath of the Cubs’ victory in 2016, fans gathered at Wrigley Field on Nov. 6, covering the bleacher walls with chalk messages. Supporters wrote names and messages, creating a vibrant display of community spirit. This impromptu event drew hundreds and highlighted the unity and passion of Chicago fans. Despite its significance, the Cubs later removed the messages during renovations, considering the display a disturbance, not a celebration.

Reflecting on the anniversary, some Cubs fans watched as Milwaukee Brewers supporters celebrated their own championship. While this might have been difficult for some, it served as a reminder of the joy felt in 2016 and the fleeting nature of success. Many believed the Cubs would repeat their triumphs, but that didn’t happen.

Theo Epstein, then the team president, resigned after the 2020 season. At the 10-year commemoration, Epstein shared his thoughts, acknowledging that achieving their goal allowed him to choose a new path. He left before another World Series appearance, passing leadership to Jed Hoyer. Under Hoyer, the Cubs struggled to replicate past success, reaching the postseason just twice in six years.

Fans expect more from Hoyer, but team owner Tom Ricketts appears comfortable with the current state. In contrast, the Brewers have consistently strengthened their bullpen, an area where the Cubs have faltered under Hoyer’s guidance. Another overhaul seems inevitable for the Cubs’ bullpen.

During the historic Game 7 of the 2016 World Series in Cleveland, an iconic moment unfolded. Jason Heyward’s motivational speech during a rain delay is credited with inspiring the Cubs to victory. Recent stadium renovations have erased physical reminders of this moment at Progressive Field. Theo Epstein recalled that network executives wanted to delay the game for better ratings. He resisted, knowing the importance of that decisive night.

Laura Ricketts, a Cubs co-owner, noted that the 2016 win was a welcome distraction amid a divisive presidential election. While the Cubs weren’t in the 2026 World Series, the memories of 2016 continue to resonate as a feel-good story.

In my column on Nov. 6, 2016, I encouraged fans to savor the joyous occasion, uncertain if such moments would come again. I hope one day that optimism is vindicated.