How Many Times Has Mark Cuban Been Married? The Truth Behind the Shark's Personal Life

Mark Cuban is everywhere. You see him on Shark Tank tearing into a bad business plan. You see him courtside at Dallas Mavericks games (well, even after selling his majority stake, the man is a fixture). You see him on social media pushing for lower prescription drug prices. But when it comes to his home life, things get a lot quieter. People often wonder about the romantic history of a billionaire who seems to have a hand in everything.

So, let's just get to it.

How many times has Mark Cuban been married? Exactly once.

Despite the "billionaire playboy" image some might expect from a tech mogul who made his first few billions in the late 90s, Cuban has been a one-woman man for over two decades. He married Tiffany Stewart in 2002, and they’ve been together ever since.

The Bachelor Years and the Mission

Before Tiffany, Mark wasn't exactly looking to settle down. Honestly, he was obsessed. If you’ve ever heard him talk about his early days in Dallas, he moved there for "fun, sun, money, and women," but the "money" part definitely took the driver’s seat. He was the guy living in a "nasty" three-bedroom apartment with five roommates, surviving on mustard and ketchup sandwiches just to keep his first company, MicroSolutions, afloat.

He’s been very open about the fact that he was a terrible boyfriend back then. He once admitted in an interview that he had several long-term girlfriends who eventually gave him an ultimatum: "It’s the business or me."

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Cuban chose the business. Every single time.

He didn't take a vacation for seven years. He worked 24/7. In his mind, he wasn't ready to be a husband because he couldn't give anyone 100% of his attention. He was "on a mission," and marriage was a "serious commitment" that he wasn't willing to half-ass.

Meeting Tiffany Stewart: The Gym Encounter

Then came 1997. Mark was 39. He was already wealthy, but not yet "global icon" wealthy. He met Tiffany Stewart at a gym in Dallas. Talk about a cliché, right? But it worked.

Tiffany was an advertising executive at the time, and by all accounts, she wasn't particularly impressed by the billionaire lifestyle. In a now-famous 2000 profile by The New York Times, she described the 24,000-square-foot mansion Mark had just bought as "impractical." She even kept her sales job and kept driving her Honda long after they started dating.

That "middle-class" mindset is likely what kept them grounded. They dated for five years before tying the knot. Mark was hesitant. He told Forbes at the time that marriage was a "no-win question" for him. But eventually, the guy who hates to lose realized that Tiffany was the ultimate win.

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A Wedding Without the Spectacle

When they finally got married on September 21, 2002, you might have expected a royal-level gala. This is Mark Cuban we're talking about. Instead, they kept it incredibly low-key.

They headed to Barbados with just 20 guests—mostly close friends and family. It was elegant, private, and quiet. It set the tone for how they would handle their marriage for the next 20+ years: Mark handles the spotlight, and Tiffany handles the "real world" at home.

Staying Married in the Public Eye

It’s actually pretty rare to see a marriage last this long in the high-stakes world of sports and tech. Since 2002, they’ve stayed remarkably stable. They have three kids: Alexis, Alyssa, and Jake.

If you follow Mark today, you’ll notice he’s actually stepping back from some of his biggest roles—including leaving Shark Tank after season 16—specifically to spend more time with his teenagers.

"My kids are teenagers and I want to spend more time with them," he told People in late 2023. He realized that while his oldest daughter, Alexis, is already off at Vanderbilt University, he still has a window of time left with the younger two.

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Why the marriage works (according to Mark):

• No "Golden Parachute" Parenting: They famously don't have a staff of chefs or butlers. They want their kids to be normal.
• The Weekend Rule: Cuban has mentioned that they had a nanny during the week when the kids were little, but weekends were strictly family time. No help. Just them.
• Mutual Respect for Privacy: Tiffany almost never does interviews. She isn't looking for fame, which balances out Mark’s natural tendency to be at the center of the room.

The Takeaway

Mark Cuban has only been married once, and he’s still married to the same woman he met at a gym nearly 30 years ago. It’s a surprisingly traditional story for a man known for disrupting every industry he touches.

If you're looking for a blueprint on how he balanced it, he’d probably tell you there is no "balance"—just priorities. He prioritized business until he reached a point where he could prioritize family.

Next Steps for You:
If you're interested in how the Cubans raise their kids without the typical "billionaire brat" syndrome, look into Mark’s interviews about his son Jake’s "candy business" at school. It's a classic example of how he's passing down the hustle without the silver spoon.

Key Facts Reference Table:

To keep up with Mark's current moves, check out his latest venture, Cost Plus Drugs, which is where he’s currently spending most of his "work" time while freeing up his evenings for Mavs games and family dinners.