He was bowling with Cubs players Wednesday night. But it's baseball he's after, and he is reportedly the leading bid, offering $1.3 billion to buy the team.
Cuban attended Kerry Wood's fundraiser to help Chicago students. And he's reaching out.
"Right now, I'm just a fan supporting a great organization, and that's why I'm here," Cuban said.
And if he's the next owner?
"I'm in a position, fortunately, where I don't have to worry about that stuff. I just have to worry about getting hitters out," Wood said.
Cuban is well-known for purchasing the Dallas Mavericks in 2000 and turning the team around with his whatever-it-takes-to-win attitude.
"Well, he turned the basketball franchise that he owned around, so he's a big businessman, he invests a lot in players," said Cubs player Aramis Ramirez.
And Cuban is known for listening to fans as well as being one, not just in Dallas but at Wrigley Field.
"We'll see him in the outfield bleachers next to the dugout. We'll give him a wink and say, 'hi.' It's good times in Chicago," said Mike Fontenot, Cubs player.
Good times that Cuban says he'll do his best to be a part of in the future.