As excitement builds for Big Brother Season 28, fans are once again revisiting some of the most iconic houseguests in the history of the hit CBS reality competition. While many contestants entered the house hoping to win the grand prize, several have gone on to build impressive fortunes through television, business ventures, social media, real estate, podcasts, and entrepreneurship.
Some became reality TV legends. Others quietly built multi-million-dollar businesses after leaving the Big Brother house.
Here’s a look at the richest Big Brother players of all time heading into Big Brother Season 28.
1. Dr. Will Kirby — Estimated Net Worth: $5–8 Million
No list is complete without Dr. Will Kirby.
The Big Brother 2 winner revolutionized reality TV strategy by openly lying, manipulating alliances, and convincing people to keep him despite admitting he couldn’t be trusted. His gameplay is still considered one of the greatest in reality television history.
Outside the house, Dr. Will built a successful career as a dermatologist, television personality, and entrepreneur, making him one of the wealthiest alumni the franchise has ever produced.
2. Derrick Levasseur — Estimated Net Worth: $3–5 Million
After dominating Big Brother 16 with one of the cleanest strategic games ever played, Derrick turned his fame into a successful media career.
He co-hosts one of the biggest reality TV podcasts, appears on television, consults on crime investigations, writes books, and has built multiple income streams since leaving the house.
Many fans still rank Derrick among the greatest Big Brother winners ever.
3. Rachel Reilly — Estimated Net Worth: $2–4 Million
Rachel Reilly has become one of the faces of the Big Brother franchise.
The Season 13 champion has appeared on numerous reality shows, including The Amazing Race and The Traitors, while continuing to build a large social media following alongside her husband, fellow Big Brother alum Brendon Villegas.
Her longevity in reality television has helped make her one of the franchise’s highest earners.
4. Cody Calafiore — Estimated Net Worth: $2–3 Million
After winning Big Brother: All-Stars, Cody expanded into fitness, influencer marketing, brand partnerships, and television appearances.
Combined with years of sponsorships and reality TV opportunities, Cody has become one of the franchise’s biggest financial success stories.
5. Taylor Hale — Estimated Net Worth: $2–3 Million
Taylor Hale transformed her historic Big Brother 24 victory into a thriving entertainment career.
The former Miss Michigan has secured brand deals, hosting opportunities, speaking engagements, podcast appearances, and television projects that continue to grow her income.
Winning both the grand prize and America’s Favorite Houseguest helped launch her career.
6. Dan Gheesling — Estimated Net Worth: $2–3 Million
Widely considered one of the greatest strategic players ever, Dan Gheesling has successfully transitioned into online content creation.
His YouTube channel, Twitch streams, business ventures, and motivational speaking have created multiple revenue streams long after his Big Brother victories.
7. Janelle Pierzina — Estimated Net Worth: $1.5–3 Million
One of the most popular houseguests in Big Brother history, Janelle has built a successful career in real estate while remaining active within the reality TV community.
She continues to earn through television appearances, partnerships, and social media.
8. Jeff Schroeder & Jordan Lloyd
One of Big Brother’s most beloved couples has continued to grow their brand through family content, hosting gigs, sponsorships, and business ventures.
Their popularity has endured for more than a decade after first meeting inside the Big Brother house.
9. Frankie Grande — Estimated Net Worth: $2–5 Million
Although already known before entering Big Brother, Frankie significantly expanded his audience after appearing on the show.
Between Broadway performances, television hosting, music, social media, and entertainment projects, Frankie remains one of the most recognizable former houseguests.
10. Nicole Franzel — Estimated Net Worth: $1–2 Million
The Big Brother 18 winner has built a successful career through influencer partnerships, podcasts, television appearances, and sponsored content.
Her loyal fanbase has helped maintain her popularity years after winning the game.
Honorable Mentions
Several other former houseguests have also built successful careers after Big Brother, including:
Britney Haynes Xavier Prather Michael Bruner Tyler Crispen Tiffany Mitchell Joseph Abdin Matt Klotz Jag Bains America Lopez Tucker Des Lauriers
How Big Brother Players Make Money
Winning the game is only one way contestants earn income. Many former houseguests continue making money through:
Reality TV appearances Podcasts YouTube channels Twitch streaming Social media sponsorships Public speaking Real estate careers Businesses and investments Merchandise sales Brand partnerships
For many alumni, these opportunities end up being worth far more than the show’s grand prize.
Big Brother Season 28 Is Almost Here
Big Brother Season 28 is expected to deliver another summer filled with blindsides, showmances, shocking evictions, and unforgettable gameplay as the long-running CBS reality competition returns with its new “Time Trip” theme. The season also marks the franchise’s milestone 1,000th episode and promises one of the biggest seasons in the show’s history. (Paramount+)
Whether a new millionaire emerges this summer remains to be seen, but history has proven that the biggest winners often cash in long after they leave the Big Brother house.
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