Drake Offers Lucky Fan 10% of Livestreamed Gambling Winnings

^{Drake performs on stage during a Vybz Kartel concert at Scotiabank Arena in Toronto on Oct. 26, 2025. (Photo: The Canadian Press / Alamy Live News)}

Drake is no stranger to livestreaming his gambling exploits to his fans and followers. But just in time for the holidays, the Canadian superstar has upped the ante with some holiday offering a percentage of his winnings during his livestreams on Kick.

The rapper announced the promotion on social media ahead of a Sunday night stream, saying that he would be streaming his Stake sessions from December 21-23. After the stream, one fan will receive 10% of Drake's total winnings.

Drake Publicizes Big Wins, Losses on Gambling Streams

Fans were directed to Stake to enter the contest. 

“Can we end my roughest gambling year on a good note??” Drake wrote on Instagram. “I want to MAXWIN and share 10% of it with you.”

Drake has indeed suffered some infamous losses while gambling this year. In August, the rapper lost $300,000 in a video in which he asked for ChatGPT’s advice on which slot game he should play on Stake. 

Just this weekend, he lost $200,000 more on a longshot bet on Jake Paul to score an upset win over former heavyweight boxing champion Anthony Joshua. Paul spent a few rounds mostly avoiding his opponent, but Joshua ultimately knocked him out in the sixth round.

Drake has previously shared about losing much more money than that, once sharing a history showing that he had lost over $8.2 million over the course of a month on $124.5 million in wagers. 

However, the biggest controversy about Drake’s gambling isn’t tied to his losses, but rather his association with platforms that may be skirting state laws in some jurisdictions.

Lawsuit Says Drake’s Stake Endorsement is Anything but Harmless 

In October, a Missouri man filed a class-action lawsuit in Jackson County Circuit Court, naming Drake, Adin Ross, and Stake.us as defendants. In the lawsuit, plaintiff Justin Kilham alleges that advertising for the popular sweepstakes casino is misleading when it claims to be a “harmless” social casino.

Drake signed a $100 million-per-year endorsement deal with Stake in 2022 and has since regularly streamed his gambling on the site to his fans as part of that agreement. At times, the star has bet millions of dollars live on stream for the world to watch, raking in both huge wins and losses.

But the lawsuit claims that Drake’s losses don’t even represent his own money, further adding to questions over the ethics of the gambling streams.

“[Drake is] glamorizing the platform to millions of impressionable fans, many of whom treat his wild betting habits like gospel,” the lawsuit reads. “What makes it even more unsettling is that Stake apparently fronts Drake and Ross ‘house money,’ so any reported losses are part of a marketing tactic designed to draw attention.”

Stake is among the many sweepstakes casinos that have been fighting battles across the United States against state regulators who say the websites constitute illegal gambling. While operators say that the dual currency system used at sweepstakes casinos mean no actual gambling takes place on the sites, regulators say that these businesses are simply using technicalities to skirt gaming regulations.