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Drake Hosted His Private 3rd Annual “Strong Women, Stronger Drinks” Dinner At Toronto’s Historic Casa Loma

The invitation-only event brought together female creators, business owners, and media personalities from across Canada for an evening of networking, dinner, and massive philanthropic giveaways.

The exclusive, all-black dress code affair quickly went viral for Drake’s jaw-dropping generosity, giving away over $1 million in cash and luxury prizes.

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Drake surprised 10 attendees with $50,000 each, and reportedly blessed another 6 standout women with $100,000 each to support their respective businesses and causes.

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Multiple guests walked out of the castle to brand-new luxury vehicles waiting out front with bows on the hoods, including a 2026 Mercedes-Maybach and attendees were also gifted luxury Birkin bags during the night.

Drake celebrating at his annual “Strong Women, Stronger Drinks” event tonight at Casa Loma in Toronto pic.twitter.com/uFrYoABaDr

— Drake Direct (@DrakeDirect) August 5, 2026

During a speech at the dinner, Drake explained that he modeled the concept after a classic 2007–2008 Toronto networking event called “What Women Want,” originally created by local entrepreneur Shinae Ingleton.

He loved that the original event required men to work while women socialized, so he adopted that spirit to throw an elevated, upscale version meant to purely appreciate and empower Canadian women.

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BLOGGER2026-08-05T11:42:33-04:00

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trixxx

Trixx

Monday–Thursday: 6:00 AM-9:00 AM

Frankie “Trixx” Agyemang is a rising star in North American comedy, known for his fearless, no-holds-barred humor and sharp insights on pop culture, relationships, and race. Winner of the 2021 Boston Comedy Festival, 2018 World Series of Comedy, and the 2013 JFL42 Big Break Competition, Trixx has been featured on Kevin Hart’s LOL Network, SiriusXM, and has opened for comedy legends like Tracy Morgan, Damon Wayans, and Cedric the Entertainer. With sold-out shows like Trixx: Unspoken Words and international performances at major festivals in London, Jamaica, and New York, Trixx continues to captivate audiences with his boundary-pushing, streetwise comedy.

trixxx

Trixx

Monday–Thursday: 6:00 AM-9:00 AM

Frankie “Trixx” Agyemang is a rising star in North American comedy, known for his fearless, no-holds-barred humor and sharp insights on pop culture, relationships, and race. Winner of the 2021 Boston Comedy Festival, 2018 World Series of Comedy, and the 2013 JFL42 Big Break Competition, Trixx has been featured on Kevin Hart’s LOL Network, SiriusXM, and has opened for comedy legends like Tracy Morgan, Damon Wayans, and Cedric the Entertainer. With sold-out shows like Trixx: Unspoken Words and international performances at major festivals in London, Jamaica, and New York, Trixx continues to captivate audiences with his boundary-pushing, streetwise comedy.

DJ-Kevin

DJ Kevin

With over a decade in the industry, DJ Kevin is a powerhouse in Caribbean music, known for his unmatched versatility, technical skill, and dynamic stage presence. A master of blending global sounds while staying rooted in his Caribbean heritage, DJ Kevin has become a fixture at carnivals and festivals worldwide, earning a growing international reputation.

Whether spinning soca, dancehall, reggae, or Afrobeats, DJ Kevin’s ability to ignite any crowd is undeniable. Collaborating with stars like Major Lazer, KES the Band, Machel Montano, Tems, and Burna Boy, he’s one of Canada’s most in-demand DJs, regularly performing at top festivals like UberSoca Cruise, Soca Brainwash, and Carivibe.

As creator and host of The Flight Zone, a syndicated radio show airing across the Caribbean and Toronto, DJ Kevin delivers the latest hits and remixes, offering listeners a fusion of authentic Caribbean sound and global influences. His passion and ability to connect with audiences, whether on stage or on the airwaves, have earned him a loyal global following and cemented his place as an innovator in the Caribbean music scene.

DJ-Kevin

DJ Kevin

With over a decade in the industry, DJ Kevin is a powerhouse in Caribbean music, known for his unmatched versatility, technical skill, and dynamic stage presence. A master of blending global sounds while staying rooted in his Caribbean heritage, DJ Kevin has become a fixture at carnivals and festivals worldwide, earning a growing international reputation.

Whether spinning soca, dancehall, reggae, or Afrobeats, DJ Kevin’s ability to ignite any crowd is undeniable. Collaborating with stars like Major Lazer, KES the Band, Machel Montano, Tems, and Burna Boy, he’s one of Canada’s most in-demand DJs, regularly performing at top festivals like UberSoca Cruise, Soca Brainwash, and Carivibe.

As creator and host of The Flight Zone, a syndicated radio show airing across the Caribbean and Toronto, DJ Kevin delivers the latest hits and remixes, offering listeners a fusion of authentic Caribbean sound and global influences. His passion and ability to connect with audiences, whether on stage or on the airwaves, have earned him a loyal global following and cemented his place as an innovator in the Caribbean music scene.

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Marxman The DJ

A mainstay in the Caribbean DJ scene since the age of 17, Marxman has been a vibrant representative of soca and reggae in Toronto and beyond. A weekly presence on Toronto radio since 2006, he launched the Planet X Wake Up Show on VIBE105 in October 2012.

With its uplifting and energizing vibe, the show has become a Friday morning favorite, setting the tone for #PlanetX listeners to kick off their weekends right!

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Marxman The DJ

A mainstay in the Caribbean DJ scene since the age of 17, Marxman has been a vibrant representative of soca and reggae in Toronto and beyond. A weekly presence on Toronto radio since 2006, he launched the Planet X Wake Up Show on VIBE105 in October 2012.

With its uplifting and energizing vibe, the show has become a Friday morning favorite, setting the tone for #PlanetX listeners to kick off their weekends right!

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Chantilly

From music journalist to publicist and now International Marketing Manager at Warner Music Canada, Chantilly leverages the power of storytelling to elevate diverse talents on the global stage. With a foundation in journalism, she brings expertise in communications, strategic media campaigns, and community building, focusing on enhancing artists’ international profiles.

Career highlights include writing up to 13 articles daily at Hot New Hip Hop, staying on top of trends, and managing publicity campaigns for artists like OhGeesy, FKA Twigs, Earl Sweatshirt, Popcaan, Central Cee, A Boogie Wit Da Hoodie, and more. Chantilly’s passion and skills continue to shape the global music landscape.

CHANTILLY-1080×1350

Chantilly

From music journalist to publicist and now International Marketing Manager at Warner Music Canada, Chantilly leverages the power of storytelling to elevate diverse talents on the global stage. With a foundation in journalism, she brings expertise in communications, strategic media campaigns, and community building, focusing on enhancing artists’ international profiles.

Career highlights include writing up to 13 articles daily at Hot New Hip Hop, staying on top of trends, and managing publicity campaigns for artists like OhGeesy, FKA Twigs, Earl Sweatshirt, Popcaan, Central Cee, A Boogie Wit Da Hoodie, and more. Chantilly’s passion and skills continue to shape the global music landscape.

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Claudia Sandz

Claudia Sandz is an honors graduate of Centennial College’s Communications and Media Fundamentals program and Humber College’s Radio Broadcasting program. She has co-hosted the live-streamed podcast Gringo Latino Talks, written blogs for popular Canadian Latin brand Barrio at TorontoLatino.com, and assisted Friday Ricky Dread on the WeLoveHipHop Network.

When not hosting at VIBE105, Claudia is a proud mom to her two daughters, Marcela and Calista. Passionate about staying active and traveling, she has explored over 15 countries worldwide. Her vibe is unmatched, and her word is always OKAAAYYYY!

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Claudia Sandz

Claudia Sandz is an honors graduate of Centennial College’s Communications and Media Fundamentals program and Humber College’s Radio Broadcasting program. She has co-hosted the live-streamed podcast Gringo Latino Talks, written blogs for popular Canadian Latin brand Barrio at TorontoLatino.com, and assisted Friday Ricky Dread on the WeLoveHipHop Network.

When not hosting at VIBE105, Claudia is a proud mom to her two daughters, Marcela and Calista. Passionate about staying active and traveling, she has explored over 15 countries worldwide. Her vibe is unmatched, and her word is always OKAAAYYYY!

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Vee Aye

Veracia Ankrah, aka “Vee Aye,” is a music and culture journalist based in Vaughan, just outside Toronto. A self-described walking contradiction, she’s a womanist and hip-hop enthusiast who embodies the spirit of Lauryn Hill, Living Single’s Maxine Shaw, and Grey’s Anatomy’s Cristina Yang.

A McMaster University graduate with an Honours Bachelor’s in Communications and Cultural Studies, Vee Aye has contributed to notable outlets like Complex Canada, Pitchfork, Exclaim!, Hot New Hip Hop, and Okayplayer.

Follow her journey @veeeracity on Instagram and X.

VEE-AYE-1080×1350

Vee-Aye

Veracia Ankrah, aka “Vee Aye,” is a music and culture journalist based in Vaughan, just outside Toronto. A self-described walking contradiction, she’s a womanist and hip-hop enthusiast who embodies the spirit of Lauryn Hill, Living Single’s Maxine Shaw, and Grey’s Anatomy’s Cristina Yang.

A McMaster University graduate with an Honours Bachelor’s in Communications and Cultural Studies, Vee Aye has contributed to notable outlets like Complex Canada, Pitchfork, Exclaim!, Hot New Hip Hop, and Okayplayer.

Follow her journey @veeercity on Instagram and X.

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DJ Baby Yu

DJ Baby Yu is a global force in the music industry, blending his passion for music with a commitment to inspiring others. Originally from Toronto and now based in Los Angeles, Baby Yu is renowned for his live blends and mixes that energize audiences worldwide.

With residencies at top venues across cities like Los Angeles, Tokyo, Bangkok, and Toronto, his reach extends far beyond the club scene. Baby Yu has achieved career highlights such as contributing to Kanye West and Jay-Z’s Watch The Throne tour and hosting shows on 97.1 AMP Radio in Los Angeles.

A prolific producer, his singles “Not My Type” and “Superstar” have garnered thousands of streams, showcasing his versatility. As a live DJ, he’s toured with artists like Young Jeezy, Offset, and Monica, while performing for icons such as Rihanna, Drake, and Chris Brown.

Through podcasts, Twitch streams, and live mixes, Baby Yu connects with a global audience, continually innovating and fostering community. Represented by S.K.A.M. Artist, he remains a trendsetter, leaving an indelible mark on music culture.

shutterstock_1988523449

DJ Baby Yu

DJ Baby Yu is a global force in the music industry, blending his passion for music with a commitment to inspiring others. Originally from Toronto and now based in Los Angeles, Baby Yu is renowned for his live blends and mixes that energize audiences worldwide.

With residencies at top venues across cities like Los Angeles, Tokyo, Bangkok, and Toronto, his reach extends far beyond the club scene. Baby Yu has achieved career highlights such as contributing to Kanye West and Jay-Z’s Watch The Throne tour and hosting shows on 97.1 AMP Radio in Los Angeles.

A prolific producer, his singles “Not My Type” and “Superstar” have garnered thousands of streams, showcasing his versatility. As a live DJ, he’s toured with artists like Young Jeezy, Offset, and Monica, while performing for icons such as Rihanna, Drake, and Chris Brown.

Through podcasts, Twitch streams, and live mixes, Baby Yu connects with a global audience, continually innovating and fostering community. Represented by S.K.A.M. Artist, he remains a trendsetter, leaving an indelible mark on music culture.

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Ricochet

Ricochet is a celebrated DJ and radio host from Toronto, Canada, known for his passion for music and ability to connect with audiences. His distinctive style and knack for discovering emerging talent have made him a key figure in Toronto’s music scene.

Starting his journey at an early age, Ricochet was influenced by Toronto’s diverse cultural sounds, including hip-hop, R&B, reggae, and dancehall. He gained recognition for his seamless mixes and high-energy performances, eventually landing a spot on FLOW 93.5 as a key contributor to the Made in Toronto Takeover show, where he championed local talent.

In addition to his work at FLOW 93.5, Ricochet collaborated with The ILL Kidz, blending genres and supporting underground artists. His ability to curate captivating playlists and create unforgettable experiences, both on-air and live, has solidified his reputation as a tastemaker and trendsetter in the industry.

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Ricochet

Ricochet is a celebrated DJ and radio host from Toronto, Canada, known for his passion for music and ability to connect with audiences. His distinctive style and knack for discovering emerging talent have made him a key figure in Toronto’s music scene.

Starting his journey at an early age, Ricochet was influenced by Toronto’s diverse cultural sounds, including hip-hop, R&B, reggae, and dancehall. He gained recognition for his seamless mixes and high-energy performances, eventually landing a spot on FLOW 93.5 as a key contributor to the Made in Toronto Takeover show, where he championed local talent.

In addition to his work at FLOW 93.5, Ricochet collaborated with The ILL Kidz, blending genres and supporting underground artists. His ability to curate captivating playlists and create unforgettable experiences, both on-air and live, has solidified his reputation as a tastemaker and trendsetter in the industry.

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DJ Flatline

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DJ Flatline

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Dee

A dynamic daughter of Jamaican soil, whose passion for culture, change, and community shines through every broadcast. With a rich background in media, leadership, and community building, Dee brings a unique blend of intellect and energy to the airwaves.

As a former CEO and founder of VIBE105 and VX3 Exchange, she knows how to present a sound that resonates deeply. You’ll hear the energy of authentic reggae and dancehall vibes mixed with cool storytelling. Don’t miss out on this daily dose of positivity, rhythm, and culture!

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Dee

A dynamic daughter of Jamaican soil, whose passion for culture, change, and community shines through every broadcast. With a rich background in media, leadership, and community building, Dee brings a unique blend of intellect and energy to the airwaves.

As a former CEO and founder of VIBE105 and VX3 Exchange, she knows how to present a sound that resonates deeply. You’ll hear the energy of authentic reggae and dancehall vibes mixed with cool storytelling. Don’t miss out on this daily dose of positivity, rhythm, and culture!

simply-leah

SIMPLY LEAH

Simply Leah is a dynamic MC, host, and DJ with roots in promotion and a lifelong passion for music. Reigniting her dream of a career in radio broadcasting, she brings her voice and vibrant energy to the airwaves, connecting with listeners and audiences alike.

Whether on the mic, behind the decks, or hosting live events, Simply Leah masterfully blends professionalism, charisma, and a love for the entertainment industry to create unforgettable experiences.

simply-leah

SIMPLY LEAH

Simply Leah is a dynamic MC, host, and DJ with roots in promotion and a lifelong passion for music. Reigniting her dream of a career in radio broadcasting, she brings her voice and vibrant energy to the airwaves, connecting with listeners and audiences alike.

Whether on the mic, behind the decks, or hosting live events, Simply Leah masterfully blends professionalism, charisma, and a love for the entertainment industry to create unforgettable experiences.

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NOBETTERNINA

A hip-hop, R&B, and trap music junkie stuck in the 2000s/2010s ?. My journey into radio was inspired by 106 & Park, and my first concert ever was Hilary Duff (the variety is crazy, I know). My most-seen artists are Drake and Tory Lanez (8-10 times each), but my favorite artist of all time is Lil Wayne.

When I’m not on air, you can catch me on the field (playing soccer), taking a nap, at a concert, or indulging in pasta, tacos, and/or some form of chocolate.

vibeDec36898-1080×1350

NOBETTERNINA

A hip-hop, R&B, and trap music junkie stuck in the 2000s/2010s ?. My journey into radio was inspired by 106 & Park, and my first concert ever was Hilary Duff (the variety is crazy, I know). My most-seen artists are Drake and Tory Lanez (8-10 times each), but my favorite artist of all time is Lil Wayne.

When I’m not on air, you can catch me on the field (playing soccer), taking a nap, at a concert, or indulging in pasta, tacos, and/or some form of chocolate.

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MC NADZZZ

Meet Nadzzz: your good vibes queen! With over 10 years of lighting up the airwaves at VIBE105, she’s a pro at keeping listeners hooked with her magnetic voice, sharp wit, and deep love for music. Nadzzz is not just a radio host; she’s a professional master of ceremonies with a Caribbean twist and a mic in hand!

Whether it’s spinning the hottest tracks, interviewing big names, or bringing high-energy vibes to live events, she knows how to keep the mic—and the crowd—on fire! When she’s not spinning tracks, telling stories, or cracking jokes on-air, she’s busy being the life of the party—literally!

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MC NADZZZ

Meet Nadzzz: your good vibes queen! With over 10 years of lighting up the airwaves at VIBE105, she’s a pro at keeping listeners hooked with her magnetic voice, sharp wit, and deep love for music. Nadzzz is not just a radio host; she’s a professional master of ceremonies with a Caribbean twist and a mic in hand!

Whether it’s spinning the hottest tracks, interviewing big names, or bringing high-energy vibes to live events, she knows how to keep the mic—and the crowd—on fire! When she’s not spinning tracks, telling stories, or cracking jokes on-air, she’s busy being the life of the party—literally!

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DJ O

DJ O-Nonymous has been on Toronto FM airwaves since 2005, contributing to the culture as a DJ and facilitator of conversations with some of hip-hop and R&B’s most notable and underrepresented artists. His roots were grounded heavily in the hip-hop scene that allowed him to find himself on concert stages touring across the country with artists like supergroup Slaughterhouse, G-Unit’s Young Buck, and many more.

Now, VIBE105 FM is where he has chosen to leave his indelible mark. DJ O likes to display contrasting balance to hip-hop with the Nice & Slow slow jam mix show most nights of the week. On weekends, you can find DJ O entertaining crowds at various local eateries, signature parties, corporate events, and weddings.

When you can’t keep up with him at live events, you can stay digitally connected to him on his own IAMDJO app and social media platforms @IAMDJO.

DJ-O-1080×1350

DJ O

DJ O-Nonymous has been on Toronto FM airwaves since 2005, contributing to the culture as a DJ and facilitator of conversations with some of hip-hop and R&B’s most notable and underrepresented artists. His roots were grounded heavily in the hip-hop scene that allowed him to find himself on concert stages touring across the country with artists like supergroup Slaughterhouse, G-Unit’s Young Buck, and many more.

Now, VIBE105 FM is where he has chosen to leave his indelible mark. DJ O likes to display contrasting balance to hip-hop with the Nice & Slow slow jam mix show most nights of the week. On weekends, you can find DJ O entertaining crowds at various local eateries, signature parties, corporate events, and weddings.

When you can’t keep up with him at live events, you can stay digitally connected to him on his own IAMDJO app and social media platforms @IAMDJO.

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