Every woman who walked through the door was greeted with a welcome gift of $1,000 in cash, setting the tone for a night built entirely around celebrating the women in Drake’s life and community. During a speech captured on video, Drake explained the origin of the event, revealing he modeled it after a gathering he attended back around 2007 or 2008 called What Women Want, hosted by a woman he described fondly as the inspiration behind his own version. He explained that the original event centered on women gathering to network and socialize, with a twist requiring men in attendance to work the event rather than simply show up as guests, a concept he clearly carried into his own annual celebration.
From there, the night turned into one of Drake’s biggest displays of generosity yet. Multiple reports indicate that ten women left the event with $50,000 each, amounting to roughly half a million dollars given away in cash alone, while other attendees reportedly walked away with prizes as large as $100,000. Guests were also gifted designer Birkin bags, adding another layer of luxury to an already over the top evening.
The biggest jaw dropping moments came from the raffle portion of the night, where Drake gave away brand new vehicles to select attendees. One woman won a brand new BMW, while Toronto Raptors reporter Kayla Grey walked away with a Mercedes Benz G-Wagon, a moment that quickly became one of the most shared clips from the entire event. Beyond the cash and cars, guests enjoyed an upscale dinner, cocktails, and entertainment throughout the night, with Drake spending much of his time personally interacting with attendees rather than making the kind of brief celebrity appearance fans often expect from an artist at his level.
That personal touch has become one of the defining reasons these events resonate so strongly online. Attendees regularly share behind the scenes moments that spread rapidly across X, Instagram, and TikTok, turning what is technically a private, invite-only gathering into one of the biggest public talking points of Drake’s calendar year. Strong Women, Stronger Drinks has quickly joined the growing list of signature Toronto events Drake hosts annually, alongside things like the OVO Golf Classic, further cementing his reputation as an artist who consistently invests time, energy, and resources back into his hometown community.
The timing of this year’s event also lands during one of the busiest and most successful stretches of Drake’s career. In May 2026, he released a trifecta of projects, “ICEMAN,” “HABITBI,” and “MAID OF HONOUR,” a run so dominant it made him the first artist in history to hold the top three spots on the Billboard 200 simultaneously. Between that chart breaking run and now this latest round of headline making generosity, 2026 is shaping up to be one of the most talked about years of Drake’s career, on the charts and off.
As details and additional clips continue rolling out from the event, one thing is clear. Drake’s hometown celebrations keep getting bigger, more personal, and more generous each year, and Strong Women, Stronger Drinks is quickly becoming one of the most anticipated nights on his annual calendar.
