Tom Dundon is making headlines again—but not for the reasons Portland Trail Blazers fans might hope. While the billionaire owner has been tightening the purse strings in the NBA, he's opening his wallet wide for pickleball.

Last Friday, Pickleball Inc. announced a massive $225 million structured investment, led by Apollo Sports Capital. According to sources, Dundon himself contributed to that eye-popping sum. That's hardly surprising, given that Dundon is the primary majority shareholder of Pickleball Inc., a growing empire that includes the Professional Pickleball Association (PPA), the popular Pickleball Central retail site, and PickleballTournaments.com software.

This latest cash infusion strengthens Dundon's hold on the sport, with Pickleball Inc. now serving as the parent company of both the PPA and Major League Pickleball. It also brings another NBA connection into the fold: 76ers owner Josh Harris is a co-founder of Apollo Global Management.

But while Dundon's pickleball portfolio keeps expanding, his approach to running the Portland Trail Blazers has drawn a very different kind of attention—and not the flattering kind.

Since officially taking over the team from Paul Allen's estate, Dundon has been hit with a wave of criticism over his cost-cutting measures. The Ringer's Bill Simmons even dubbed him "El Cheapo." Among the eyebrow-raising moves: the Blazers reportedly didn't bring their two-way players to road playoff games, Dundon personally ensured the team avoided late-checkout fees at its hotel, and fans at Portland's home playoff games were left without the customary free t-shirts.

On the basketball side, the most pressing issue is the team's coaching situation. Interim head coach Tiago Splitter led the Blazers to the playoffs after Chauncey Billups was arrested and placed on leave amid a federal investigation, but it appears Splitter won't be retained for the long term.

For Blazers fans, the contrast is hard to ignore: Dundon is pouring millions into pickleball while pinching pennies in Portland. Whether that strategy pays off on the court remains to be seen—but in the world of sports business, all eyes are on how this two-sport owner balances his checkbook.