Is Mark Cuban the world’s most eccentric billionaire? 5 surprising moves from the Shark Tank tycoon, from offering US$1 million for Donald Trump to shave his head to buying a private jet online

Jul 26 , 2023

Mark Cuban is a billionaire, philanthropist and a cast member of Shark Tank. Photo: @mcuban/Instagram

Mark Cuban, the 64-year-old American businessman, investor, philanthropist and TV personality, has achieved, experimented with and enjoyed a lot of things.

One may call his humble parenting style a sham or his investments outlandish. (By May 2015, this shark invested in 85 deals across 111 Shark Tank episodes for a total of US$19.9 million.) But it doesn’t take a genius to guess that Cuban is simply a man who does as he pleases.

“There’s no one more competitive than me. Business is a sport,” the billionaire once said. But all work and no play is not the Cuban way. He worked hard to make his millions – and knows how to spend it too, often with results just as out-there as his business sense.

Here’s a closer look at the crazy and unpredictable antics of this fearless entrepreneur.

1. He offered US$1 million for Donald Trump to shave his head

Mark Cuban is a multibillionaire. Photo: @marc_oconnell/Twitter

Nearly a decade ago, the Dallas Mavericks basketball team owner put his sense of humour to good use. Donald Trump offered to give US$5 million to charity if then-President Barack Obama produced university transcripts and passport applications.

Is Kobe Bryant’s daughter Natalia Beyoncé’s most stylish intern?

Former US president and republican presidential candidate Donald Trump attends the Oakland County Republican Party Lincoln Day Dinner in Novi, Michigan, US on June 25. Photo: Reuters

Cuban clapped back at the unreasonable request by announcing he’ll pay US$1 million toward a charity of his choice – if Trump shaves his head, per Forbes.

2. He has been fined millions for badmouthing refs

Dallas Mavericks owner Mark Cuban exchanges words with one of the referees during the fourth quarter against the Utah Jazz in their first-round playoff game in Salt Lake City, in 2001. Photo: AP

Sports is filled with adrenaline rushes, high-riding emotions – and flaring tempers. No wonder the Dallas Mavericks owner has accumulated millions in penalties for swearing.

Candid Cuban was fined a hefty US$600,000 by the NBA for making public comments deemed detrimental to the league in 2018, and on several other occasions before that.

3. He managed a Dairy Queen for a day

Dallas Mavericks owner Mark Cuban shows off his first attempt at an ice cream cone at the start of his shift at Dairy Queen fast-food restaurant in Coppell, Texas, in 2001. Photo: AFP

Motormouth Mark Cuban has his razor-sharp tongue to thank for landing him in trouble more times than he’d prefer. During the teething period of his Mavericks ownership, Cuban famously snapped that the NBA director of officials Ed Rush wasn’t fit to manage a Dairy Queen. As expected, controversy knocked on his door as the NBA fined him a record US$500,000 for repeated public criticism of NBA officiating.

Mark Cuban working at Dairy Queen. Photo: Handout

But the master marketer got the last word – by managing a Dairy Queen for a day himself. Parrish Chapman, who owned the Coppell Dairy Queen, was thoroughly impressed: his store usually rang up 2,000 tickets daily, but with Cuban on the cash register, it was quickly estimated to be 6,000 by the end of the day, per The Dallas Morning News.

Who is Kevin Costner’s estranged wife, Christine Baumgartner?

4. He holds the record for the biggest single e-commerce transaction

Mark Cuban isn’t afraid to flaunt his wealth. Photo: @mcuban/Instagram

What’s a business tycoon without their private plane? In 1999, Cuban sold his video portal Broadcast.com to Yahoo for US$5.7 billion – and apparently celebrated his success by splurging on his own set of wings.

Private planes are a billionaire’s staple. Photo: Handout

It wasn’t his purchase that raised eyebrows, but his payment method. Cuban bought a Gulfstream V business jet for US$40 million – over the internet. This earned him a Guinness World Record for the largest single e-commerce transaction, and the record is still unbroken today.

5. He bought the US$250,000 American Airlines AAirpass after making his first million

American Airlines’ AAirpass. Photo: American Airlines/Wikimedia Commons

Cuban clearly has a passion for travelling: the first thing he bought after earning his first million was the coveted American Airlines AAirpass, he told CNBC Make It. With unlimited first class tickets to any destination, the world became his oyster thanks to his 1990 purchase.

This article originally appeared on Luxurylaunches.

Want more stories like this? Follow Style on Facebook, Instagram and YouTube.

Millionaires and billionaires

The NBA Dallas Mavericks owner may be one of the world’s most fearless billionaires, making news for his investments and antics alike – like when he offered US$1 million for Trump to shave his head
He’s been fined millions for making controversial comments at the NBA, once worked a day at Dairy Queen, and splashed out US$250,000 for an American Airlines AAirpass