There’s no denying the fact that Drake, or Aubrey Drake Graham, has come a long, long way since his first steps towards fame as Jimmy Brooks in Degrassi: The Next Generation.
Since then, he’s amassed not just a $250 million fortune but also countless awards for his music. There are the five Grammys, six American Music Awards and two Brits, to name just a few of them. He’s also sold over 170 million units and is undoubtedly one of the world’s best-selling artists. The Drake empire reaches out far beyond just music. From his very early days he has had multiple business interests including sponsorships from brands like Sprite as well as setting up his own recording label OVO Sound in collaboration with the renowned producer Noah “40” Shebib and business partner Oliver El-Khatib.
Bu it’s another of his endorsement deals that has hit the headlines recently, the $100 million a year contract that he was said to have had with the online crypto and sportsbook casino, Stake.
The Deal in Question
Ever since its US launch in 2017 Stake has built a reputation for using celebrities and sports people to act as ambassadors for the brand. In 2023 they even became sponsors of an F1 racing team, Sauber Motorsport. The deal that they struck with Drake was that, in exchange for live streaming his gambling sessions on the site, he would receive up to $100 million a year in free stake money.
Initially this took place on Twitch. However, the service subsequently decided to restrict the streaming of gambling, instigating to total ban on sites that were not licensed to operate in the US. This led the founder of Stake to set up their own streaming service called Kick. In order to attract even more gambling streamers this offered a far more generous revenue split than many of its competitors.
Up until recently the relation between Drake and Stake seemed to have been running along smooth lines with Drizzy even taking part in a live stream to celebrate the brand’s eighth birthday. But in the summer, it all seemed to go wrong.
Can’t Pay, Won’t Pay?
The crux of the issue seems to have been that when he tried to withdraw his winnings from Stake this was repeatedly blocked. In a series of increasingly angry messages on social media to his 142 million followers worldwide he implied that he was being victimised by Stake. This seems to be at odds with the experience of industry expert Daisy Harrison of Casino.org who ranks Stake as one of the fastest paying online casinos out there, which suggests this is more of a personal grudge than a poorly ran business, if Drake is telling the truth of course.
As well as severing all links with the brand Drake has been calling on fellow endorser Trainwreck to also pull away from Stake. To underline the end of the relationship Drake has also subsequently deleted his Kick account.
Bets and Threats
Drake had previously been reporting on his big sportsbook wins in sports ranging from football to MMA and boxing. This, however, seems to be at odds with some of Drake’s other pronouncements over the last few months. Back in June 2025 he announced that he had lost over $8 million gambling on the site and suggested that he was desperate for a big win to announce to his fans. So, given this volatile situation, it can be hard to see where exactly the truth lies.
The one thing that can be certain is that Stake’s founders Ed Craven and Bijan Tehrani will certainly not be receiving Christmas cards from Drake this year. Not only has he called Craven a snake, he’s also offered to meet him in the boxing ring to, literally, thrash out their differences.
The Feud Machine
It has to be said that this is just another in a long line of feuds started by the singer. Among the people he’s singled out for them are Kanye West, Puff Daddy, The Weeknd, Jay-Z and Ludicris. How genuine these have been it’s hard to know as in the high-stakes world of music any publicity or notoriety is undoubtedly good for business.
He’s also had more than his fair share of legal trouble over the years. This has either been on the receiving end being sued by other songwriters for copyright infringement or suing others for the improper and unauthorised use of his image in publicity material as he did with the jewellery company GEMMA Ltd.
Whether the current beef is going to be one that ends up in the law courts remains to be seen, although it would probably be in everyone’s best interests if it was resolved amicably and without a punch being thrown. But, as the man himself has sung in the past, when Trust Issues come to the surface sometimes there can be no going back.
