Hip-hop’s dangerous bet on the gambling industry

Earlier this month, Drake posted a black-and-white video to his Instagram Reels, set to the contemplative strains of Wiz Khalifa’s “See You Again.” But instead of a heartfelt salute to Paul Walker, Drake repurposed the ballad to pay tribute to something else: gambling. As Charlie Puth croons and piano keys twinkle in memory of Vin Diesel’s fallen bestie, we see clips from the past year of Drake risking millions of dollars on virtual roulette, anxiously ripping a hookah at his kitchen counter as he stares intently at his computer screen and roleplays his own private Uncut Gems. The caption? “It’s been a long time without a big win…” and the tag for Australian crypto-betting platform Stake, which launched an official partnership with Drake last year. Sports betting and casinos are hardly new territory for rappers who have money to play with, but the gambling industry has increasingly turned to hip-hop to acquire legitimacy, using rappers and sometimes rap music itself as a way to lure possible marks.

Since 2018, when the Supreme Court struck down the Professional and Amateur Sports Protection Act, sports betting has been legalized in over 30 American states, bringing a backroom industry into the spotlight. If you’ve watched even a minute of professional American sports in the last five years, you’ve most likely been inundated with splashy advertisements for sportsbook apps like DraftKings, FanDuel, and BetMGM enticing you with confusing promotional offers. Even professional wrestling, a form of entertainment predicated on fixed outcomes, has gotten in bed with companies like DraftKings, which has official sponsorships with both WWE and rival AEW. The popularity of sportsbooks skyrocketed with COVID-19 pandemic; not only were so many Americans sitting at home with more spare time on their hands, but most of us were also worried about money and desperate for alternative income streams.

Like pretty much every commercial industry these days, from car insurance to over-the-counter heartburn medication, celebrity endorsements are crucial to marketing the gambling game. Pro athletes of almost every type have found easy money stamping their approval on sportsbooks: Michael Jordan, Mike Tyson, the Mannings, Marshawn Lynch, to name only a few. But when it comes to risky ventures like cryptocurrency, flipping homes, and betting, the involvement of celebrities raises valid questions about their own complicity in possibly devastating financial schemes. Concern has risen regarding rates of addiction, as well as the ethics of advertising and gambling live-streams. Gambling addiction, or “problem gambling” as the industry terms it, is regarded by the American Psychiatric Association as a legitimate disease on the same level as alcohol and drug addiction. But regulation of legalized betting has done little to address the dangerous side effects for some users — compared to the almost $12 billion in revenue generated in the United States in 2022 by the sports betting industry, only about $110 million was spent by state governments on resources and support for those struggling with gambling addiction.

In some cases, rap music has been used more literally as a promotional tool for sportsbook start-ups. For the 2023 NBA playoffs, DraftKings recruited Rick Ross, Fat Joe, and The LOX to record an official song entitled “The Game” — in-between footage from the court, statistics and analytics subliminally flash on the screen, almost like a winking acknowledgment of marketing’s manipulative properties. Last year, a DraftKings advertising campaign “embedded” the brand name in original songs commissioned from rappers like Dave East and Polo Perks, filled with clunky product placement bars like “Lately I been feelin’ like a Draft King” and “Hit Up DraftKings / I bet a hunnid on myself.”

If you needed any more evidence of how deeply embedded betting is within the larger sports industry, Fresco Trey’s spon-con “Draft Kings” appeared on the soundtrack for NBA 2K22. While hip-hop’s endless crossover with professional sports might make it a natural fit in the gambling world, this kind of ad campaign illustrates how the entertainment industry so often views rap music as little more than a musical billboard, ripe for product placement and licensed name-drops — DraftKings hasn’t expressed the same desire to hire country or rock artists to “embed” their brand into original songs, at least not yet.

Then again, the lines between recording artist and commercial spokesperson have always been blurred; radio was largely built by companies like Light Crust Flour and Mother’s Best Flour, who employed artists in-house like Bob Wills and Hank Williams to promote their brands on-air. Branded commissions aren’t new in rap either, but what separates these DraftKings-sponsored tracks from, say, the “brandcore” wave of early 2010s rap is that these songs directly hawk the product itself, where companies like Red Bull and Adult Swim used commissioned music to generate cultural clout.

The questionable nature of betting start-ups also makes that direct endorsement a thornier issue. Only a few months after Nicki Minaj announced her official partnership with Maxim Magazine as the “global ambassador” for their sportsbook MaximBet, the service shut down, demonstrating how fly-by-night the industry can be. Especially for emerging artists like Polo Perks and Fresco Trey, branded commissions from gambling companies offer not just the promise of further visibility, but an additional payday, without any of the risk that actual DraftKings users entertain — as with celebrity endorsement of cryptocurrency, almost all of the risk is mitigated from wealthy sponsors to the normal person who might be enticed into betting it all on the desire to be as successful as their favorite rapper.

While it’s unclear whether Dave East actually uses DraftKings, other celebrity spokespeople for sportsbooks are consistent users. Increasingly, rappers are not just gambling themselves, but gambling on the gambling industry, seeing sportsbooks as a lucrative and low-effort revenue stream and another page in their investment portfolio. Drake — username DeepPockets6 — has a working relationship with Stake.com, and while he’s certainly an active player on the site, that business partnership likely cushions him from the losses the average gambler might incur—it wouldn’t be a great look for Stake if their highest-profile celebrity sponsor lost very real money using their service. But it’s a mutualistic relationship: Stake.com is on some level basically paying Drake to pay them by way of continually placing massive bets with their bookies. Having such a high-profile customer benefits Stake in other ways, too; the specter of Drake has served to overshadow the company’s legal woes, including data leaks and hacks.

Unsurprisingly, given his unquenchable thirst for capitalism, Jay-Z has had more luck when it comes to his transition to gambling mogul. In 2021, Jay announced an almost $350 million investment in Fanatics, a sporting goods company that deals in everything from snapbacks to trading cards to NFTs, in addition to operating the official digital storefronts for leagues like the NFL and NBA. Fanatics entered the betting marketplace this year with its service SportsBet, which is currently only available in Kentucky, Ohio, Massachusetts, Maryland, and Tennessee. But Jay’s not content to only let other people deal the cards. After applying for a New York gaming license alongside Philadelphia 76ers co-owner Michael Rubin, Jay-Z has set his sights on the newly-opened frontier of casino gambling in the New York City metro area. In an open letter published in the New York Post, the New York Daily News, and the Amsterdam News, RocNation shared its desire to break ground on Caesar’s Palace Times Square — though Jay is only one of many entrepreneurs fighting for the hotly-contested rights to the city’s only casino license.

But like so much of Jay’s financial advice, the gambling industry only benefits those who already maintain a significant amount of capital. When you have more money than you can count, it’s easier to afford the inevitable losses that come with trying to strike it rich on a big-time bet, in both gambling and investment. The dream of being the impresario in the back of the house who hoards all the chips pays off for very few; for the average person, it usually just ends in being another sucker losing money at the table, clinging to the desperate illusion that the next hand will turn your life around.

Rappers like Drake and Jay-Z didn’t build their own wealth through gambling, but their association with the gaming industry fosters an unconscious perception that if you pay to play, you just might become a billionaire too. The legitimizing effect of celebrity endorsements on an addictive product has increasingly come under scrutiny by state and local governments — including Drake’s native Ontario, which recently passed legislation to ban gambling advertisements featuring “celebrities who would likely appeal to minors.” Celebrities may not risk much financially when endorsing gambling platforms, but they do risk their reputation by getting into a business that could very well harm their own fans.

Rap Column is a column about rap music by Vivian Medithi and Nadine Smith for The FADER.