Drake marked the third year of his Strong Women, Stronger Drinks dinner this week, an event that has grown into one of the most talked about gatherings on his annual calendar. The invite only celebration continues to highlight the rapper’s focus on supporting women while paying tribute to the role Black women have played in building spaces for connection and career growth.
An idea born from a 2007 gathering
The dinner traces its origins to a networking event Drake attended nearly two decades ago, organized by Shannae Ingleton, founder of the talent and entertainment company Kensington Grey. That gathering, called What Women Want, brought together women across industries to build relationships and celebrate their success. The experience stuck with Drake and eventually became the blueprint for the Toronto event he now hosts each year.
A dinner built around ambition and community
Drake has described his vision for the evening as a space where accomplished women from different fields can gather, exchange ideas and form connections over a shared meal. The guest list typically includes entrepreneurs, executives, creators and community leaders, all recognized for their contributions in their respective industries. Rather than functioning purely as a celebrity affair, the dinner positions itself as a platform for collaboration among women who might not otherwise cross paths professionally.
Set inside a Toronto landmark
This year’s dinner took place at Casa Loma, the castle style estate that has become one of Toronto’s most recognizable venues. Event producer Shantel Clarke of Reserved X Events oversaw the planning, while the production company That Good, led by founder Catriona Coco Smart, helped shape the night’s overall experience. Clips from the event quickly spread across social media, showing Drake greeting guests throughout the evening.
Guests walked away with six figure surprises
The night became known almost as much for its generosity as its guest list. Every attendee reportedly received $1,000 simply for showing up, a gesture that set the tone for what followed. As the evening continued, Drake distributed a series of far larger rewards.
- Ten women each received $50,000 in cash.
- Several guests were gifted crocodile Birkin bags.
- Additional attendees drove home in brand new G-Wagons.
Among the night’s biggest winners was TSN reporter Kayla Grey, who received both a $50,000 prize and a limited edition Mercedes Benz AMG G 63 SUV worth more than $200,000. Drake’s former Degrassi co star Andrea Lewis, who played Hazel Aden on the series, was also among the attendees who left with a gift and shared her excitement on social media afterward.
Part of a larger pattern of hometown giving
The dinner fits into a broader pattern of community focused events Drake has built around Toronto over the years. He remains closely tied to the annual OVO Golf Classic charity tournament and has hosted other gatherings, including apology themed brunches tied to his Janice, STFU catchphrase. Together, these events have become a recurring way for Drake to celebrate his hometown while directing attention and resources toward local causes and personalities.
A celebration with lasting impact
While the extravagant prizes generated most of the online buzz, the dinner’s underlying goal remains rooted in recognition. By spotlighting the achievements of Black women in business, media and entertainment, the event continues a tradition that began with Ingleton’s original 2007 gathering. As Strong Women, Stronger Drinks enters its fourth year on the horizon, it has cemented itself as a fixture of Drake‘s Toronto calendar and a night that blends celebration with genuine tribute to the women shaping their industries.
