Shark Week on the Democratic Bench
By Jenny Braddock
06/21/2025
The President’s approval rating is so underwater, if he were scuba diving, he’d need a second tank. JD Vance would have likely chosen dental surgery over seeing his Vice Presidential polls. Trump is still threatening a third term… oh joy, and Democrats are staring at 2028 like a man at the blackjack table who just split aces and drew two threes.
Mark Cuban may say he’s not running, but we’ll still put him on the Bench instead of calling him a Wildcard, because if he did decide to run — he has the resources and access to more, and there’s nothing to stop him. On Thursday’s The Bulwark Podcast with Tim Collins, Mark was posed the question, “Somebody I kind of trust said that they asked you to send in VP vetting papers and you said, no, the list would be too long. Is that true?” Mark responded, “My response was, I’m not very good as the number 2 person. And so if the last thing we need is me telling Kamala, you know, the president that no, that’s a dumb idea. Right. And I’m not real good at the shaking hands.”
So not a complete repudiation of the idea, but not a serious lean-in either — but we’ll still keep him warm. Because in a cycle like this — when the bench has plenty of utility players but not many broadly marketable stars — the party might just start drafting billionaires like it’s the NBA.
He’s less terrifying than JD Vance by orders of magnitude and more coherent than RFK Jr. by yet more orders of magnitude. And in the race for 2028 that seems less and less distant every day, that could be a compelling résumé.
Background Check – Mark Cuban in 90 Seconds
Mark Cuban isn’t a Democrat by birthright or ideology. He’s a Democrat the way some people are vegans — not because they love vegetables, but because they hate factory farming.
He made his fortune in the early days of the internet, selling Broadcast.com to Yahoo for $5.7 billion just before the bubble burst. Since then, he’s been in the rarest of billionaire categories: the ones who cashed out early and actually stayed rich.
And he seems to be one of the few people who’s actually good at being rich. He stays active in business, sure, but he’s not chasing ever more power or clout like a rabid dog — see Elon, Zuckerberg, or anyone else whose net worth seems inversely proportional to their grasp on reality. He seems to enjoy his wealth, but still hangs out with his high school friends and rugby buddies instead of hiding on mega yachts. That makes him broadly appealing — even in the manosphere, where money is worshipped but authenticity is rare.
He bought the Dallas Mavericks in 2000 and ran them like a startup, hovering courtside in jeans and shaking up the league’s old-money ownership culture. It was his time as the owner of the Mavs that permanently embedded him in the fabric of pop culture. They won a title with Dirk Nowitzki in 2011, and Cuban’s fingerprints were on every part of it — often quite literally.
He became a household name through Shark Tank, playing the deal-making pragmatist who cuts through nonsense faster than his fellow Sharks can hit their buzzers. On a personal note, I was working with the producers of a different show at the same network right before Shark Tank launched. Let’s just say he made the cut, and I didn’t.
He co-founded Cost Plus Drugs, a pharmacy startup aiming to undercut middlemen and bring transparency to drug pricing — one of the few billionaire ventures that didn’t feel like a PR grab. The business is equal parts social commentary, public service, and functional enterprise. With each filled prescription, he’s pointing out just how jacked our health care system is.
And while he doesn’t always talk about it, he also took a hit
