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Drake Hands Out Six-Figure Cash Prizes And Luxury Cars At His Annual Women’s Event

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Source: @champagnepapi/Instagram
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Aug. 5 2026, Published 2:39 p.m. ET

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Drake has a track record of showing up big for the women in his orbit, and this week was no exception. On Tuesday, August 4th, the rapper hosted the third annual edition of his Toronto gathering, Strong Women, Stronger Drinks. Once again, the event turned an evening of networking into a life-changing night for several guests.

Held at the historic Casa Loma mansion, the event welcomed women with a $1,000 cash gift the moment they walked through the door, according to Billboard. From there, the night only got bigger: video clips that circulated widely online showed Drake surprising guests with cash prizes as high as $50,000 and $100,000, along with a raffle for two luxury vehicles, a BMW and a Mercedes-Benz G-Wagon. Toronto Raptors reporter Kayla Grey was among the winners, driving off with the G-Wagon.

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The concept behind Strong Women, Stronger Drinks isn’t new for Drake. As Billboard reported, he explained during a speech at the event that the idea traces back to an event he attended in the late 2000s called What Women Want, where men were expected to work the room rather than simply attend. He said he wanted to recreate that same spirit of women gathering to network and support one another, with the added twist of turning the evening into a giveaway meant to change lives.

Drake told the crowd the invite list was made up of women “doing incredible things in your respective fields,” whether they were early in their careers or already at the top, and encouraged guests to use the night to connect and learn from each other before the giveaways began.

The event lands during one of Drake’s busiest stretches as an artist. In May, he released a trifecta of projects, “ICEMAN,” “HABIBTI,” and “MAID OF HONOUR,” a run that made him the first artist to hold the top three spots on the Billboard 200 simultaneously.

Whatever the motivations behind it, Strong Women, Stronger Drinks has become one of the more talked-about moments on Drake’s calendar each year, a reminder that celebrity philanthropy, however it’s packaged, can still create real, tangible impact for the people on the receiving end.

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KerbiLynn – Kerbi Rucker
By: Kerbi Lynn

Kerbi Lynn is the managing editor at Her Agenda. She is an entertainment and culture journalist from Atlanta, GA and featured in several publications including, MEFeater Magazine, Black Wall Street Times, and BOSSIP. Before pursuing journalism full-time, she obtained her bachelor's and master's degrees from The University of Georgia (Go Dawgs!). In addition to her strong passion for entertainment, Kerbi Lynn loves to write about current events and their impact on mainstream culture.

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