Michael Jordan had something he needed to get off his chest. Ninety minutes before the start of the first game of the 1993 National Basketball Association finals, the then two-time defending champion motioned to sports commentator Ahmad Rashad to “get a camera”.
Dressed in a broad-shouldered taupe suit jacket and Ray-Bans, Mr Jordan was disdainful as he spoke.
“Whenever I walk away from this game, I think that’s the only thing that people are going to say was a bad thing about Michael Jordan,” he said. “No, I didn’t commit a crime, but, ‘he gambled’.”
American celebrity culture demands that its stars — and especially its sports stars — be divinely perfect specimens, without vice and above reproach.
The revelation at the time that Mr Jordan had a penchant for high-stakes gambling threatened to derail his basketball career: then-NBA commissioner David Stern hired a former federal judge to investigate his off-court activities and determine if the player had violated league rules.
Almost three decades later, Mr Jordan — whose athletic skill earned him the nickname His Airness — looks to be getting the last laugh on his gambling critics.
Shares in American fantasy sports outfit DraftKings closed 8 per cent higher on Wednesday after it was disclosed he would take an equity stake in the Boston-based group and join its board as a special adviser. The size of his investment was not disclosed.
The longtime owner of the Charlotte Hornets NBA franchise and sneaker brand pioneer is having a year for the ages: his playing days — including his love of gambling — are the subject of hit Netflix mini-series, The Last Dance.
And amid a global reckoning over racial injustice, he has pledged $100m over the next 10 years towards organisations which benefit the black community, in a joint commitment with his eponymous Nike-owned shoe brand, making him a key figure in the politicised business of US sport.
Donald Dell, Mr Jordan’s agent for the first decade of his playing career, said his former client had matured into someone more comfortable in taking a leadership role. “He’s growing more and more [into a] corporate statesman for the sport, that’s his real goal,” he said.
Born in Brooklyn and raised in North Carolina, Mr Jordan was a gifted athlete from a young age and distinguished by an all-encompassing drive to win. That passion fuelled not only his athletic pursuits but also, by his own account, his enthusiasm for gambling, particularly for blackjack and betting on rounds of golf.
Mr Jordan testified in a 1992 money-laundering trial that he once paid the defendant, James “Slim” Bouler, $57,000 in gambling debts.
The next year, amid the 1993 playoffs, a former associate published a supposed tell-all book describing an alleged gambling addiction, leading to the impromptu television interview with Mr Rashad.
The subsequent league investigation into Mr Jordan’s betting activities in the summer of 1993 cleared the star of any wrongdoing. In an interview that year, Mr Jordan famously said he didn’t have a gambling problem but “a competition problem”.
That Mr Jordan has now taken an official role with a sports betting company points to a dramatic shift in US attitudes towards gambling in recent years.
“Anyone that knows anything about Michael knows he likes to gamble, and now all the things that were taboo a long time ago — well, there’s gambling on everything now,” said Sonny Vaccaro, the sports marketer who helped bring Mr Jordan to his first shoe contract with Nike in 1984.
Industry experts point to centuries of Puritan-influenced US values which largely restricted the scope of legal betting. The 1992 Professional and Amateur Sports Protection Act effectively banned sports betting nationwide, but the law was struck down in a Supreme Court ruling in 2018.
Since then, 18 states have legalised the practice, with another 11 considering or implementing such legislation, and more than $23.5bn has been wagered at authorised sports bookmakers according to data from Legal Sports Report.
That has been a boon for outfits like DraftKings, which launched in 2012 as an online daily fantasy sports app and has since expanded into sports betting in the wake of the Supreme Court ruling.
The company, which listed in April through a special-purpose acquisition company, or Spac, had revenues of $323m in 2019.
DraftKings and Mr Jordan declined to comment for this story.
But interviews with people who have worked with him reveal the tie-up is reflective of an individual who is coming into his own as a businessman, even if aligning with a gambling company is a reminder of a trickier period earlier in his career.
“Michael is bright as hell, he knew that question would be asked,” Mr Vaccaro said. “With DraftKings, now the world should understand that Michael is making all the calls.”