Former NFL wide receiver Michael Irvin earned the nickname ‘Playmaker’, winning three Super Bowls. But he would have made way more money if he were a ‘Dealmaker’ — billionaire Mark Cuban had offered Irvin that opportunity. A misjudgement on his part caused him to lose a paycheck that would have been worth at least $600 million. 

“Mark Cuban wanted a meeting with us, wanted to do business with me,” he said on his Netflix podcast, The White House. “Offered us 20% of Broadcast.com. We didn’t take it. Couple of years later, he sold [for] $3 billion.

“Every time I saw Mark Cuban after that, he looked at me and said, ‘You know how much your take would have been?’”

The deal arrived on Irvin’s table after he had started the company Players Communication Network (PCN). Indiana businessman Mark Cuban, by 1998, had acquired the majority ownership of Broadcast.com. His offer to Irvin was an invitation to work together with the Cowboys legend and boost the very first digital sports broadcasting project. This was Cuban’s first major acquisition after selling the company he founded, MicroSolutions, in 1990.

The billionaire was not the established name he is today. Michael Irvin might have been wary of a deal that sounded too good to be true. He was heading towards the end of his professional NFL career at this point, in 1999. He was forced to retire after a tackle by Philadelphia Eagles defensive back Tim Hauck caused him a cervical spinal injury. Imprudent business decisions would have spelled doom for the WR.

But as fate would have it, taking the cautious route caused him to miss out on a jackpot. 

In 1999, Yahoo! acquired the company for $5.7 billion (not $3 billion, as Irvin said), setting Cuban up with a handsome paycheck for good. It was one of the biggest trades on Wall Street at that time. The acquisition was entirely in stock, and Cuban became a billionaire.

So, if Irvin was to get 20 percent, he would have gotten a whopping $1.14 billion as his share. The number is far more than the $600 million Irvin estimated.

But Cuban, ever the smart businessman, must’ve sensed the crisis coming right afterward.  Unfortunately, Yahoo! was forced to shut down the company by 2002, as the dot-com frenzy crashed. But Cuban sold most of his Yahoo stock and was able to keep his fortune. He later went on to invest in the Dallas Mavericks, where he owned the majority stake. The NBA team became a very competitive one in the league for a good few years after this. 

Michael Irvin has also made some good business choices in retirement, especially with his career in the media. But with Cuban’s offer, Irvin could stand to earn so much more.

Irvin worked as an analyst on NFL Network for nearly 25 years, further establishing himself as a popular favorite. He also runs a successful podcast today, and his YouTube channel has more than 104,000 subscribers. The aforementioned White House Podcast began only this January. In 2022, per FOX, the former WR partnered with TradeZing, a Web3 platform for Gen Z crypto trading. This time, Irvin was not going to miss the train at his stop.

Irvin interestingly asked No. 1 pick Fernando Mendoza to listen to Mark Cuban, after a shocking rumor started to make the rounds before the draft. No credible information ever came out of it, but the investor was reportedly ready to pay Mendoza $39 million to stay in college football for one more year.

“If Mark Cuban is offering $39 million and Mendoza decides to go to the NFL… in the NFL, we would call that… that’s a bad move, man,” Irvin said in a video on his YouTube channel. 

Clearly, the former Dallas Cowboys icon seems to have learned his lesson.