Drake Gave 10 Women $50K Each. Here’s Who They Are And Why It Matters

Drake held his third annual Strong Women, Stronger Drinks event this year at the Casa Loma mansion in Toronto and gave out massive prizes.

The event was invite-only, with a 140-person guest list that included entrepreneurs, influencers, and other prominent women in their respective industries. Guests received a $1,000 cash welcome gift and enjoyed an upscale dinner at the event.

“All of you who are doing incredible things in your respective fields,” Drake shared during his speech. “Whether you’re grinding or ascending to the moon, or somewhere in between. We hope that you can be social, talk to each other, learn from each other, and we have an incredible evening for you.”

10 women were picked out of the attendees and gifted an additional $50,000 each. Other luxury items, from Birkin bags to BMWs, were raffled out to attendees. According to reports, six attendees received $100K, including tattoo artist Ayasha Luna and streamer and content creator Sarah Farrugia, received $100k from the ICEMAN rapper to invest back into their businesses.

We reached out to the event organizers and Drake’s PR rep to get official confirmation on all winners but received no response. We will update, if/when we hear back. In the meantime, we were able to independently confirm five of them who were honored with the $50K gift. Here’s what Her Agenda knows about each winner.

The Canadian actress and singer got her breakout role as Hazel Aden in Degrassi: Next Generation and was Drake’s former costar. Since then, she’s been in several TV series and TV movies, including Nickelodeon’s musical film Spectacular! and Hulu’s How to Die Alone.

Andrea Lewis describes the moment of winning the generous $50,000 gift as “very unexpected.”

“It’s been a real blessing. We’ve seen each other grow up, and I feel very lucky to have a friend like him and that, no matter where we are in the world or our personal journeys, we always manage to stay connected,” Andrea told Her Agenda. 

Andrea plans to reinvest the money back into her creative work, including investing in her team and talent at her production company Jungle Wild Productions which she founded in 2012, helping create short films and projects like her docuseries The Black Beauty Effect on Netflix.

Kayla is a WNBA reporter at The Sports Network and one of the winners of not only the $50,000 cash prize, but also a Mercedes-Benz G-Class vehicle. 

Kayla Grey became an anchor and reporter for TSN in 2017. In 2018, she became the first Black woman to ever host a flagship sports highlight show, The Shift, in Canada. Her fame and influence in sports journalism have earned her multiple accolades, including being named one of Refinery29’s PowerHouse Women of 2020 and one of the Top 25 Women of Influence in Canada for 2021 by Women of Influence. In 2022, Kayla was received the Change Maker Award from the Academy of Canadian Cinema and Television at the 10th Canadian Screen Awards.

“YOU ARE INSANE,” she thanked the rapper in an Instagram post.

Helen (@skinbyhelen) is a Toronto-based skincare and lifestyle influencer. Her content is centered around treating her dry skin and deep-diving into skincare ingredients and K-beauty skincare trends. She’s built up a loyal community of skincare fanatics who trust her honest reviews and engaging visuals. Most recently, she created a three-part glow-up series in preparation for her wedding, from trying products to eliminate her acne to doing at-home laser hair removal. Earlier this month, Helen announced her first community-based event in Toronto—a Matcha Walk across the city where people can try out new matcha cafes.

She has nearly 200,000 followers across TikTok and Instagram.

“no words” she captioned a Reel on Instagram regarding the event.

Natasha (@natashascloset) is an Afro-Latina fashion and lifestyle creator based out of Toronto and Los Angeles. A recent nursing school graduate, shes know for her work get-ready-with-mes using the tag #scrubfit and vlogs as she invites viewers to join her in her everyday life. In 2024, Natasha created her own fashion series called “Style Syllabus.” In this series, she and her audience embark on a self-taught journey through concepts typically taught in fashion school, proving that formal education isn’t always necessary for pursuing one’s passions. As a vibrant creator, Natasha exemplifies the belief that it’s never too late to learn and chase your dreams. 

In true Natasha fashion, she told a story time to her audience of over 400,00 followers across her socials about the event, including having a dance battle with Drake. 

The beauty influencer (@jasmine.alishaa) was one of the lucky few who won the cash prize. A part of the 2026 Sephora Squad Canada, the Toronto and New York-based beauty influencer posted a get-ready-with me before the event. One of her most popular TikTok videos to date features a concealer from NARS Cosmetics covering up her acne spots. She has over 450,000 followers across YouTube, TikTok, and Instagram. She’s also a marathon runner and most recently ran the 20th annual Maybelline Women’s Half Marathon in New York City back in April 2026.

Jasmine graduated with a Master of Education in Social Justice in 2024 from the University of Toronto. 

Drake’s inspiration for the event comes from Shannae Ingleton Smith, the co-founder of influencer agency Kensington Grey, who held the very first “What Women Want” networking event in 2008.

“There was an event by a lovely woman. She used to do an event called What Women Want. It was essentially women gathering to network, to socialize and to be a man at the event, you had to work. I always loved that aspect of it. We would show up and work the event because that’s what the event was about,” said Drake in a speech to the audience. 

The event is aimed at celebrating women who are doing “incredible things” in their respective fields, he further explained. 

Andrea Lewis tells Her Agenda that the night served as a reminder of how powerful major industry platforms and community can be when they step up to champion women.

“On a personal level, it reinforces that long-term success comes down to balance. You need those major room-shifting moments and heavy-hitting partners, but you also need a tight-knit inner team, people who know your vision intimately, and advocate for you when you are not in the room, and keep your personal priorities front and center,” she told Her Agenda.