Crains Chicago Business / Danny Ecker

Andrew Berlin picked the right time to switch his Chicago baseball ownership stake.

It was 20 months ago that the CEO of Chicago-based Berlin Packaging bought a minority share of the Chicago Cubs, who tomorrow will begin their first World Series in 71 years.

He was one of several investors that the Ricketts family, which owns the franchise, brought on last year to help finance its ongoing Wrigley Field renovation project and redevelopment of the ballpark’s surrounding area.

But Berlin’s background was unique. Unlike his fellow new minority stakeholders, the 56-year-old already knew what it was like to claim ownership of a major Chicago professional sports team. Since 2007, he had been a limited partner in ChiSox, the controlling entity of the White Sox led by Chairman Jerry Reinsdorf.

Berlin transferred his Sox investment into a trust for his kids (he no longer has a personal investment in the franchise) when he bought into the Cubs, who have been one of the best teams in baseball ever since.

“You think it’s a coincidence?” Berlin joked in an interview with Crain’s before the team clinched its first National League pennant since 1945.

His powers as a Cubs part owner are far greater than his influence was with the Sox, where his money was on the table but he had no input on the team’s business decisions. At Wrigley, he sits on an advisory board with his fellow investors, eager to share his input.

“My opinion is valued, that’s the difference,” said Berlin, who also owns the South Bend Cubs, the team’s single-A minor league affiliate. “To me, that is very gratifying.”

Also making him happy: The Cubs will be swimming in championship revenue if they can beat the Cleveland Indians in the Fall Classic.

Berlin has attended every Cubs postseason game at Wrigley Field so far this month. He sits a few rows behind the Ricketts family’s seats along the third base line, next to the Cubs’ dugout.

Not bad for a guy who just six years ago held his birthday party at U.S. Cellular Field.

The Glencoe resident, who grew up a Cubs fan, said one of the biggest thrills of his Cubs ownership tenure has been getting to know the team’s young stars and watching them succeed. “I’m jealous of the experience they’re having and living vicariously through them,” he said.

But while winning a World Series would be a dream scenario for him as a fan and part owner, Berlin said it would be an especially meaningful win for the city.

“I think Chicago needs something to be proud of right now,” he said. “There’s so much difficulty and so much outrage and so much going on in the city—the crime, the pension debt, the arrears that the city and state are in—all these things that are just really weighing on the city and our national and international image. I think this would give the city something to be proud of. Even White Sox fans have to admire this team.”

As for envisioning his own celebration if the Cubs win their first World Series since 1908, Berlin said it will start with drying his tears of joy.

“I’m not a drinker,” he said. “But maybe I will be that day.”