As one of five finalists to purchase the franchise from the Tribune Co., Cuban was happy to stump for why he deserved to lead the organization. As it ended up, the Ricketts family bought the Cubs instead, and the rest is history as they say.
So how does Cuban look back on that experience?
"The experience was great, but I'm glad the Ricketts got it," Cuban said on the McNeil & Parkins Show on Wednesday afternoon. "They've done a great job. They won a World Series, and that's the pinnacle of what everybody thought could never happen. And so I'm really glad the Ricketts got it. They've done a phenomenal job. I would've had fun, but all's well that ends well for me and both sides."
Reflecting now, Cuban believes his failed bid turned out to be a blessing.
"No regrets at all," Cuban said. "And the reality is, when I was going into it (in 2008), my kids were really young. Now they're 10, 13 and 16, and they're too much fun. And between 82 games for the NBA and 162 games games (for MLB), plus the playoffs for both, I would've missed a whole lot of them growing up that I'm glad I'm not missing."