Despite winning six NBA championships with the Chicago Bulls, Reinsdorf told his friend, he might never win a coveted World Series title with the Chicago White Sox.
"Absolutely, I thought it might not happen," Reinsdorf said. "I said, 'I'm going to be 70 next year, and I've been doing this for 24 years. I wonder if it will ever happen.' "
The White Sox chairman needs to wonder no more. After the South Siders finished off Houston with a 1-0 victory Wednesday night at Minute Maid Park, completing the 19th sweep in World Series history, Reinsdorf and his team had that World Series title they had sought after for close to nine decades.
It was deemed by Reinsdorf as the crowning achievement of his 25-year ownership with vice chairman Eddie Einhorn. The same feelings came from White Sox players and coaches, alike, when directly questioned about winning one for Reinsdorf.
"Jerry Reinsdorf, one of the biggest reasons I wanted to win this was for him," said manager Ozzie Guillen. "I was thinking about now that Jerry Reinsdorf can hold something he wanted to hold for a long time -- a World Series trophy."
"The happiest moment of the year for me was to see Jerry Reinsdorf get the World Series trophy," hitting coach Greg Walker added. "[The coaches] had our whack at it as players and didn't get it done for him, but these guys did. It's a proud moment for all of us."
During the past month, when Reinsdorf has gone from a silent owner to one of the most quotable men in town, the White Sox chairman has talked extensively about the differences between winning an NBA title and a World Series title. He made it clear again Wednesday that there simply is much more attention placed on what takes place during baseball's postseason.
He also has shared a personal belief from Spring Training in regard to his selection of the White Sox to win the American League Central. He didn't know how far they would advance from that point, but then again, he didn't think the White Sox would ever build up a 15-game lead within the division.
And he certainly didn't think that lead would shrink down to 1 1/2 games over the hard-charging Indians.
"There is no one star on this team, no real huge stars," Reinsdorf said. "They play as a team, and this sort of thing has to happen for a team to win a World Series."
Reinsdorf laughed half-heartedly when asked if the ghost of Shoeless Joe Jackson had been exorcised. His team doesn't believe in ghosts or curses or any other media-contrived sort of scenarios.
The White Sox believe in winning, and they came up with the ultimate victory on Wednesday. Reinsdorf shared the glory with his family, stopping one of four or five impromptu talks with the media to hug his grandson, Joey.
And then he returned to speak about the title he never thought would arrive.
"We have a great organization, from the scouts to the marketing people, and every player and every coach," Reinsdorf said. "They all played a part in the title.
"There are a lot of happy people in Chicago right now. It's amazing how our fans love this team and how the team belongs to them. I'm so happy for them.
"I won't realize until tomorrow what this means," Reinsdorf added. "Now, every other team in baseball has a longer drought then we have to win the World Series. After hearing about 88 years for so long, that feels pretty good to say and hear."
It felt good for the players and coaches to say that they helped Reinsdorf fulfill his dream.
"Nobody understands what kind of person he is," said Walker. "If you don't like him back in Chicago, well then you don't know the man that we know.
"I'm not just saying this. I came back to baseball and my primary goal was one reason. That's what I just got done seeing in the other room."
Scott Merkin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.