He remembered, too, the tears he shed when the White Sox, the team he bought in 1981, won the 2005 World Series. For a few sweet months that fall, a sports franchise had a city in the palm of its hand.
White Sox gear was draped over tombstones around Chicago to commemorate the end of an 88-year wait for a championship. Reinsdorf laughed as he remembered the boy on the parade route holding a sign that said, "I've waited six years for this."
Mostly, though, this was a night for reflection and larger lessons. Reinsdorf said that 32 years in professional sports have shown him again and again how they can make a substantive and positive impact on communities and in the lives of men and women.
That's the part of his legacy of which Reinsdorf is most proud. He got to a point in his life where he could use his influence for good, and he has done that over and over. In ways large and small, on the field and off, his has been a wonderful life of accomplishment and service, and Reinsdorf was honored for it on Wednesday night with the Lifetime Achievement Award at the 2013 Sports Business Awards at the Marriott Marquis.
"Did he make his community a better place to live?" Commissioner Bud Selig said during a video tribute to Reinsdorf. "There can't be anybody left in Chicago who thinks that he didn't make that city a better place to live."
The thing to understand about Reinsdorf is that he's revered by his employees, respected by his peers. He can be tough and demanding, but his employees are incredibly loyal to him. The longer they've worked for Reinsdorf, the more they've come to see his values as the same ones they'd like to have for themselves.
"His legacy in the sports world is going to start with his championships," NBA Commissioner David Stern said. "That's just the way people focus. But the more important legacy is the social responsibility one, which is being a community asset, including diversity, aggressiveness and inclusion that he has come to be known for."
Reinsdorf began to understand that sports could stand for something larger when he sat at Ebbets Field in 1947 and watched Jackie Robinson break the game's color line. By the simple act of wearing a baseball uniform, Robinson changed the world forever.
"Those of us in team sports are very lucky, very, very lucky," Reinsdorf told the gathering of executives from teams, marketing, television, etc. "Not only because we don't have real jobs, but because we're able to bring joy to so many people and because we can make the world a better place."
When he's pressed about the things his White Sox and Bulls have done that make him proudest, Reinsdorf does not begin with championships. He speaks of the community volunteers the White Sox have organized for neighborhood tasks, ranging from cleaning up parks to refurbishing schools.
There's the James Jordan Boys & Girls Club and Family Life Center built by the Bulls. There's the youth baseball league sponsored by the White Sox that has helped more than 60 kids receive college scholarships.
"It's great to grow baseball players," Reinsdorf said. "It's more important to grow kids that can go to college and get an education."
The White Sox give active members of the United States military free tickets. Every Chicago fireman gets two free tickets a year.
"Many players on their own have foundations and causes they support," Reinsdorf said. "Over the last year, Bulls players have made nearly 250 charitable appearances. And former players made about 120 appearances. Last year, 13,000 people were part of the Bulls' community events. The White Sox have similar statistics."
Reinsdorf said that while he was proud of how much good his two teams have done, he knows that there's similar work going on around virtually every MLB and NBA team.
"While winning is wonderful, you can't do it very often," Reinsdorf said. "And what I'm really most proud of being in sports is the wonderful things that sports teams do for their community. Bud Selig often says that baseball is a social institution and has great responsibilities. He constantly exhorts us to take that responsibility seriously. David Stern has made the NBA a world-class doer of good things. Both of my clubs have given millions of dollars to worthy causes and have numerous programs of which I'm extremely proud."
Through the years, Reinsdorf has learned plenty of lessons about owning a sports team. One of them is that the longer he has owned the White Sox and Bulls, he has come to understand that real ownership -- that is ownership in its emotional form -- rests elsewhere.
"We are just custodians," Reinsdorf said. "The real owners are the fans. It's their teams, and we just have the privilege of running them."
Reinsdorf credited his success to hiring the right people and allowing them to do their jobs. He said he'd been blessed in so many ways he couldn't begin to name them all.
"I've always worked hard, and I've tried to be totally honest," Reinsdorf said. "Honestly, luck and the help of others has played a much larger part in my success than my own efforts."
Some of the people who know Reinsdorf best would disagree with that assessment. They would say that a man with ambition and dreams, a man who always tried to do the right thing, has made the world a better place.
"Despite all the accomplishments and success, Jerry has remained a regular guy, a smart and generous regular guy," said George Bodenheimer, former ESPN president.