The Biggest Boss is back on the press run, and this time Rick Ross is selling the dream of dating him like it’s a free upgrade to first class. Rozay pulled up to DJ Clue’s BagFuel podcast and explained, in full Maybach Music fashion, that getting on his wave is supposed to be life altering. According to the Miami rapper, “a month with me, 2 months with me could change your life forever, shorty,” which is why he says his former flames stay on good terms long after the situationship fades.
Ross painted the picture as a man who handles his romance with transparency, runs zero games, and roots for his women to win even when long term commitment isn’t on the table. He told Clue that everybody doesn’t deserve a real relationship with him, but if he’s rocking with you for the season, you deserve the boss treatment. He’s already shared that five kids in, plus a 2:30 a.m. phone call schedule he revealed to Linsey Davis on ABC News, walking down the aisle is a wrap before it ever starts.
Now the sermon sounds good in podcast form, but Baller Alert did the homework. A quick tour through Rick Ross’s dating history says most of these women were already moving like bosses, and several are doing better than fine without him in the picture.
Take Lastonia Leviston, the mother of his oldest daughter Toie. Lastonia dated Rozay way back when he was still chasing his first record deal, and in 2026 she’s a Netflix reality star on W.A.G.s to Riches, the founder of the Instatique boutique brand, and the proud mom of a daughter who runs her own beauty company, Ashanti Beauty. She built that lane independently of any Maybach.
Then there’s Tia Kemp, who has turned the co parenting saga into a full personal brand. She was a co host on Zeus Network’s Aunt Tea Podcast alongside Tokyo Toni and Karlissa Saffold, she dropped a memoir titled Tia’s Diary: Deeper Than Rap, sat down with Yung Miami on Caresha Please, and runs a TikTok and Instagram presence that keeps her booked for press. Whether you love her commentary or not, she’s monetized her story on her own terms.
Lira Galore was famously engaged to Rozay back in 2015 with an 11 carat ring that the rapper took back after she called the relationship toxic on Iyanla Fix My Life. Cut to today and Lira is a Fashion Nova ambassador with over 4 million Instagram followers, a daughter named Khaleesi, and a long standing partnership with Pierre “Pee” Thomas, the CEO of Quality Control Music. Different boss, different chapter.
Briana Camille, the mother of three of his children Berkeley, Billion, and Bliss, parlayed the breakup into the Fox Soul reality series Getting Back to Bri, where she documented the messy split and her co parenting journey. She walked away with real estate ties across Florida and Georgia, a child support arrangement reported at over $11,000 a month, and her own platform that doesn’t need a feature from Rozay to stay lit.
Pretty Vee, who quietly dated Ross from 2022 to 2023, kept her own bag the entire time. The Wild ‘N Out cast member sits at an estimated $5 million net worth, has more than 6 million Instagram followers, and continues to land acting roles and brand deals on the strength of her own comedy brand.
And while Keyshia Ka’Oir only spent a few months with Rozay in 2013 and 2014, she went on to marry Gucci Mane, build the Ka’Oir Cosmetics empire, and become one of the most recognized celebrity wives in hip hop. Foxy Brown, who he was briefly linked to in 2008, was already a platinum selling Def Jam rap legend before they ever crossed paths. Even his most recent reported flame, Cristina Mackey, has used her time in the spotlight to push sales on her own brand at mackeybody.com.
So when Rick Ross says a month in his orbit changes your life, the receipts suggest a lot of these women were already on game. Some of them used the Rozay chapter as a springboard, a few used it as content, and the smartest ones never let the Maybach Music branding define them. The Biggest Boss isn’t lying about being a boss. He’s just leaving out the part where the women he dates tend to be bosses too, before they meet him and long after he moves on.
For now, Rozay says he’s keeping his options open, his calendar packed, and his 2:30 a.m. check ins active. Whether that’s truly a lifestyle upgrade or just a season of content for the next ex to monetize, we’ll let the timeline decide.
