Greenberg: As Cubs celebrate their World Series anniversary, let’s raise a glass to Joe Maddon

Posted July 16, 2026 11:04 am

By Jon Greenberg

Twelve years ago, Joe Maddon was introduced as the Cubs’ new savior at a Wrigleyville bar where he promised everyone a shot and a beer. The Hazleton Way, he called it.

In the years before Maddon came to town, Cubs fans drank because of managerial decisions, not in honor of them, but he was brought in to change everything and he did.

Throughout the years, the idea was that if a Cubs manager ever won a World Series, he’d be set for life in this city. No more paying for drinks or dinners. A job as long as he wanted it.

Well, Maddon got the Cubs to the World Series. He got them to the parade. But reaching the mountaintop only means you have to go back down and do it again. Winning a World Series in the second year of a five-year deal did not result in a contract extension and three years later, Maddon was looking for a new gig. His eponymous restaurant shuttered and everyone moved on.

The rest of the core, from Theo Epstein to Anthony Rizzo, left in the coming years. The team’s audacious dreams of a dynasty were waylaid by the cold, hard reality of sports. The Cubs made it to one more NLCS in 2017, and it took until 2025 for them to win another playoff series.

“The main reason it’s hard (to repeat) is because it’s so hard to win one,” Epstein said to me in 2017.

Mike Ditka got seven more years with the Bears after winning a Super Bowl and Ozzie Guillen got six after breaking Chicago’s long drought on the South Side. Maddon got just three.

“I really thought it would last longer,” Maddon said in a recent phone conversation. “Quite frankly, I thought we would be there a little bit longer than five (years). The first four years we go to the playoffs and the record overall for five years is one of the best five-year stretches they’ve ever had.

“And I’m not taking total responsibility for this, I’m just saying overall, the culture was flipped, we played good baseball on an annual basis, three consecutive NLCS and that’s not easy to do. I would have hoped to stay there longer, I’m not going to deny that, but it’s a short shelf life doing this particular job, and honestly, I’m so fortunate to have had the opportunity to manage there. The Chicago Cubs are the big leagues of the big league.”

As the second stage of the Cubs’ 10th-anniversary festivities takes place this week, I talked to Maddon, who at 72 isn’t looking for another baseball job. He has, in a way, returned to nature. He lives on a golf course, owns some other land, mows his grass, plants his tomatoes and flowers, talks about baseball when he wants to and lives life as only he can.

“My days are full,” he said.

But now he’s called back to Chicago. Ten years is too little time to truly grasp the meaning of an event, but at the same time, the 2016 team deserves its spotlight.

“It is the proverbial blink of an eye,” Maddon said. “It’s like it did happen yesterday. It’s very fresh. You can see it, smell it, taste it. You remember what you were doing there.”

Everyone got together for a private party before the Cubs Convention in January and Maddon said that helped break the ice. Then, Rizzo and David Ross did a podcast series reliving the season with players, coaches and executives. They will do a live show at the Chicago Theatre on Thursday. The team will be feted at Wrigley Field on Saturday, including the unveiling of a “Champions Gate” at Gallagher Way outside of the stadium.

On Sunday, Maddon will bring back his charity event “Thanksmas” to raise money for the homeless. He has a new foundation called “Two Burnt Feet,” and you hope he makes it back here more often for business and pleasure. He certainly feels the love in the city.

“People on the street, I mean you just get stopped all the time and in a good way, it’s never to the point where it becomes intrusive,” Maddon said. “It’s just a handshake, a thank you, a ‘thanks for what you did.’ They don’t want an autograph, they don’t want a photograph, they just want to interact and it’s so cool. I really enjoy walking about downtown Chicago for that reason.”

I understood the very real friction that developed between the Cubs front office and Maddon, so the breakup wasn’t a surprise. Maddon’s voice had less sway with his veterans as the years went on and the wins decreased. Back in 2016, some of his pitching decisions late in the World Series were cause for concern and debate. He wasn’t perfect. But in the end, Maddon raised a trophy and there were no more curses.

Much as the Cubs needed Epstein to remake the organization, they also needed Maddon to manage it. He was the perfect man for a stressful, almost impossible job that defeated many before him. In the first two seasons, especially, it went just as Epstein and Hoyer envisioned when they met Joe for beers in that RV park in Florida.

“I had a wide berth in regards to implementing things that I want to implement,” Maddon said of those early years that set the tone for his unique clubhouse culture, which is probably best described by the Maddon-isms “Never let the pressure exceed the pleasure” and “Try not to suck.” He created an environment that helped the Cubs win and survive a 3-1 deficit in the World Series. Listening to Maddon’s interview with Rizzo and Ross, you get the idea that they appreciated his contributions even more as the years went on. Players win and lose games, but the manager sets the standard.

“When you’re down three games to one and come back and win a World Series on the road, that just speaks to the quality of the group, and I mean, these guys never quit,” he said.

After getting fired with the Angels in 2022, Maddon has become a bit of a baseball Cassandra, warning everyone about what the game has lost. While he was a forerunner in baseball’s adoption of advanced analytics, he also became a skeptic on how baseball has evolved over the past decade. In his mind, the changes have excluded the personal touch that he specialized in.

“I don’t think that in today’s game front offices are necessarily looking to provide a wide berth for managers to bring into existence what they believe is important based on intuition, experience, etc.,” he said. “Today, the game is run more by front offices based on their mores and what they believe is the right way to do things. So there’s a difference.”

He’s not completely wrong. A lot has changed. Maybe that pendulum swings back. After all, Epstein has helped “fix” the game with rule changes, and the Cubs gave Craig Counsell a record-setting deal and a lot of power. But in terms of persona, Maddon is a lot like Ditka and Guillen. Loved, criticized and ultimately respected.

Chicago is not shy about commemorating its sports heroes and while the post-2016 Cubs experience has been full of complaints and regrets, their legacy will only grow as the years go by, Maddon included. Honestly, they should’ve gotten their own statue instead of sharing space on some gate.

What will we say about this team in another decade?

“We’re going to be bigger and better in 10 years, are you kidding me?” Maddon said. “You think about Tinkers to Evers to Chance. I mean, my God, these are mythical figures by now. This is almost like Zeus and stuff. It’s going to take on that kind of grand appearance at some point because the stories, I think they’re amplified in a good way as the past moves forward. So I think that is going to happen.”

In the coming years, it shouldn’t take a reunion to bring Maddon to Chicago. And when he’s here, he should arrive with both empty pockets and stomach. There should be a mayoral fiat that he never pay for a meal or a drink here again.

And from now until the end of days in Chicago, we should toast to Joe Maddon once a year. I know just the drinks.