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Mark Cuban was the highest-profile owner in the NBA during his two decades leading the Dallas Mavericks, and he wishes things had gone down a bit differently.

For over two decades, Mark Cuban was the most visible owner in the NBA. He served, both officially and unofficially, as the Dallas Mavericks' general manager, head cheerleader, media coordinator, and face of the franchise.

However, by 2023, he decided he wanted to pursue other ventures and sold a majority share to the Adelson family for $3.5 billion.

In the following seasons, the Boston Celtics, Los Angeles Lakers, and Portland Trail Blazers would all be sold for $10, $6.1, and $4.3 billion, respectively.

Had Cuban waited and allowed the market for franchises to be set, he could have walked away with a lot more money. However, with a net worth of $6.5 billion, it's not the money that haunted him.

Mark Cuban Calls Out Current Mavs' Ownership

Months after the sale, the Mavericks found themselves in the NBA Finals. They would lose to the Boston Celtics, although Cuban was the team's biggest supporter during that run, still a visible face with his 27% equity still in the franchise.

As a part of the sale, Cuban and the Adelsons had a handshake agreement that he would still get to call some of the shots. After the infamous Luka Doncic trade, it was clear that Cuban had lost control of the team.

Cuban never regretted selling. He just wishes that he had vetted the bidders better than he did.

"I don't regret selling," Cuban said while appearing on the Intersections Podcast. "I regret who I sold to. Yeah. I made a lot of mistakes in the process, and I'll leave it at that."

The Adelsons, who made their money in Las Vegas as casino builders, wanted to use their ownership of an NBA team as a building block to eventually allow casino gambling in the Lone Star State. Since they took over, the Texas legislature has made it clear that they have no plans to change the laws, effectively cutting off Adelson's main source of income.

There have since been conspiracy theories floated around that the family will sell. If they do, Cuban is expected to make a bid or be a part of a forward-thinking ownership group.

Cuban was raised in Pennsylvania and went to school in Indiana, although he quickly realized that the fan has to come first. While he wasn't always the most popular owner, it was clear that he was having more fun than any other team head in the league, and fans appreciated that effort. The Adelsons, meanwhile, have made more than one misstep, prioritizing the bottom line over wins or the fan experience.