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Bitcoin Ballers: The Celebrities Who Made Bank Before the Crash

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Source: Kanchanara/Unsplash

Nov. 20 2025, Published 1:25 a.m. ET

It started with hobbyists and bedroom-based speculators on the margins, but then it soon entered the mainstream and built a playground for the A-listers we all know and love. We’re talking, of course, about Bitcoin and the rollercoaster rise that it has been on in recent years.

Before anyone could pause for breath, celebrities had moved from talking heads and endorsement centerpieces to movers and shakers in their own right. They were buying, building, and branding themselves around the digital success they were achieving in the crypto world, and for good reason. The wave was there to be ridden from their point of view, and big paydays were earned along the way.

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Early Celebrity Crypto Adopters

They came, they saw, they conquered. These are the people who had already made it big in their specialist fields, and now they were looking to try something new and see what all the noise was about. Would they be able to leverage their public profiles and infectious media personas to take their crypto positions to the next level? Only time would tell.

Hollywood’s Burgeoning Tech Set

The likes of Ashton Kutcher, Gwyneth Paltrow, and Reese Witherspoon had the energy and investment smarts to get involved in a range of blockchain startups and Bitcoin investments early on. Silicon Valley has long had something of a magnetic pull that is felt by the mainstream and admired from afar in Hollywood. If we take Kutcher as an example, we learn that before long, he was creating a venture fund of his own and making crypto donations on live TV. This was one of the most eye-catching examples of the niche world of digital currencies entering mainstream cultural awareness for the first time.

The Music Industry Develops a Crypto Beat

Go a little deeper into the fascinating world of entertainment, and we see artists like Snoop Dogg, DJ Khaled, and Akon embracing cryptocurrency. Sometimes they were promoting their own NFT collections as works of digital art, other times they were talking about far-reaching blockchain projects. We had Akon’s “Akon City” and his forward-thinking digital token plan as a marker of the scale of the ambition in the music industry and the desire of many to crossover into crypto. This was about personal branding and elevation as much as it was about creating new touchpoints for fans and followers.

The Sports Endorsement Phase

As things continued, we were seeing NFL icon Tom Brady and soccer superstar Lionel Messi getting crypto sponsorships, often being paid their salaries in digital tokens. Market volatility was a far-off concept, with sports stars seeing the merits of crypto as a way to build their brands beyond their teams and the leagues they competed in. This was about embracing fandom, trying to go viral in a new field, and thinking of ways to communicate and spread awareness of what they were all about. It was the epitome of a personal branding crossover, and it seemed to be working.

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Crypto Mania & Celebrity Endorsements

Crypto mania really seemed to be gathering pace when we saw a shift from it being a niche financial endorsement to a platform for the athletes and celebrities themselves. They were rebranding blockchain projects with their personal personas and using their profiles and charisma to attract interest from whole new audiences and markets.

Shifting From Investments to Endorsements

If we look at 2020–2021, we see a bull market in which celebrities seemed to be launching NFTs every week, all while fronting exchanges and releasing “exclusive drops” aimed specifically at their existing fans. Kim Kardashian, Matt Damon, and Paris Hilton were just a few of the media names to get in on the act, and they were not shy about putting themselves in the spotlight. Before we knew it, the faces we had spent years watching on TV and the big screen were now ambassadors for a new wave of fintech products that we naturally seemed to trust as a result.

A Sudden Public Backlash

Just as things seemed like they would only trend in one direction, an unexpected crypto winter reversed the narrative and flipped the script, bringing with it a range of class-action lawsuits. Social media criticism was suddenly rife, and a shift in the underlying sentiment from “getting rich” to “being cautious” was now in play. Without wishing to paint any one particular celebrity in a negative light, we can step back and see a bigger picture of misunderstood volatility. The crypto market had an innate relationship with price and value over time that many simply did not have the experience to fully comprehend, if at all.

The Aftermath of the Crash

As quickly as the celebrities poured into the industry, they began to head for the exit. The tap seemed to have been largely turned off, and the public had grown wary of what was being offered, but would there be anything left? In the immediate aftermath, it may not have been clear, but we can now look back with the benefit of hindsight that only the passage of time can provide.

Today, we see blockchain innovation, emerging digital artists, and more conservative fintech partnerships still in existence, each having matured as a result of the crash. The celebrities and public figures who chose to remain shifted from endorsement deals and speculation to strategic investments in tech, AI, and content creation startups that are built on a foundation of blockchain technology.

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Crypto & Casinos: The Celebrity Connection

One of the first industries to really make moves with cryptocurrencies and their underlying blockchain technology was online casinos. Their need for trust, transparency, and provable fairness made them the perfect proving ground for a new approach that many hoped would elevate the player experience.

Drake Joins the Blockchain Casino Phenomenon

Drake’s high-profile partnership with Stake, a crypto-based online casino, brought digital gaming and the influence of celebrities together in a new way. While Drake brought the spotlight, Stake built the infrastructure that allowed it to operate in accordance with the necessary international regulations.

Drake joined livestreams, promoted the brand on his socials, and put on online events watched by millions of fans. He wasn’t endorsing gambling—he was promoting a brand to his followers and fans, highlighting what was on offer in a way that was not designed to promote a shift towards unsustainable play. It was an example of marketing reach, not of anything more than that.

And far from just the man known by music fans around the world, this shift started to make waves in esports and gaming venues that utilized blockchain tech. It is a powerful example of how entertainment and crypto-driven fintech merged to provide new forms of fan engagement, as opposed to simple direct promotion of the fintech advancements.

The Importance of Regulation and Responsibility

A quick look at any of the crypto casino resources available online will highlight that gambling and crypto both face strict oversight. Media personalities who come on board now include prominent disclaimers and work within the constraints of strict compliance frameworks. At the same time, global regulators are continually tightening their advertising rules to ensure that legislation is never outpaced by innovation.

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Looking to the Future

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The crypto boom period taught us all that fame can be used to amplify the impact of financial moves, but that risk still needs to be understood. As time went on, we saw that the intriguing nature and significant future promise of blockchain tech began to blur the lines between entertainment and strategic investment, altering the risk profile in ways that few understood. Some left richer, some left more cautious, and the market matured greatly as a result of what happened.

What can we say about the future? All signs are that the next wave of digital fame and progress will come as a result of smart innovation built on transparency, not rampant speculation.

The information provided in this article is for general informational purposes only. Gamble or play responsibly. If you or someone you know has a gambling problem, help is available. Call 1-800-GAMBLER. If you’re in the U.K. and need help with a gambling problem, call the National Gambling Helpline on 0808 8020 133 or go to gamstop.co.uk to be excluded from all UK-regulated gambling websites. We disclaim any liability for any loss or damage arising directly or indirectly from the use of, or reliance on, the information presented.

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