Overview
- Drake hosted the third annual Strong Women, Stronger Drinks at Casa Loma on Tuesday, Aug. 4, and attendees received $1,000 welcome gifts plus multiple larger prizes that were filmed and shared on social media.
- Multiple outlets report that ten women were awarded $50,000 each and that several guests received $100,000 prizes, though exact counts vary between reports.
- TSN reporter Kayla Grey posted that she won a Mercedes‑Benz AMG G 63 G‑Wagon and $50,000, a moment widely corroborated by video from the event.
- Reporters and attendees captured giveaways of high‑end vehicles and designer items including a Maybach, BMW and Range Rover, but news organizations differ on the night’s overall payout with totals ranging from roughly $500,000 to more than $2 million.
- Drake said the event was inspired by an earlier networking gathering called 'What Women Want' and framed the night as a place for women to connect, a format that has become a recurring, highly visible part of his Toronto calendar and that has drawn public praise and questions about how celebrity philanthropy is targeted.