Sean “Puff Daddy” Combs and Cassie Ventura, 17-Year Age Difference

Sugar Daddy Sean Puff Daddy Combs and Cassie Ventura

Sugar Daddy Sean Puff Daddy Combs and Cassie VenturaWith a net worth of about $580 mil­lion, Sean “Puff Daddy” Combs was the rich­est hip hop artist of 2013, beat­ing out icons like Jay-Z and Dr. Dre. Combs didn’t make his money just off rapping—he’s also a suc­cess­ful record pro­ducer, entre­pre­neur, and actor. In fact, most of his money comes from non-musical work.

Sean “Puff Daddy” Combs started his career as the founder of Bad Boy Records in 1993, which went on to sign rap icon Noto­ri­ous B.I.G. Four years later, Combs released his first album, which won a Grammy, and it’s now cer­ti­fied seven-times plat­inum. That was just the begin­ning for this aspir­ing businessman.

In 1998, Sean “Puff Daddy” Combs launched his award-winning cloth­ing line, Sean John, and in 2001, he made his act­ing debut in the film Made with Jon Favreau and Vince Vaughn, fol­lowed by the drama Monster’s Ball along­side Halle Berry and Billy Bob Thorn­ton. He also has a deal with Dia­geo (the bev­er­age com­pany that owns Cîroc and Smirnoff vod­kas), which means he earns a sig­nif­i­cant per­cent­age of their prof­its, and he now owns Liz Claiborne’s cloth­ing line Enyce.

Combs has actu­ally never been mar­ried, but that doesn’t mean he hasn’t had any­one to share his money with—if not his five kids, then the beau­ti­ful women he’s been in rela­tion­ships with over the years. He had his first son in 1993 with designer Misa Hylton-Brim, his high school sweet­heart. In 1998, his sec­ond son was born in 1998 with his on-again-off-again girl­friend Kim Porter.

After their rela­tion­ship ended, Combs famously dated pop super­star Jen­nifer Lopez for two years, fol­lowed by Bruce Willis’ cur­rent wife Emma Hem­ing and super­model Naomi Camp­bell. He even­tully reunited with Kim Porter, who gave birth to their twin daugh­ters in 2006. The celebrity cou­ple ended their rela­tion­ship the fol­low­ing year, and the breakup was any­thing but ami­ca­ble. While Kim Porter was preg­nant with the twins, Sean “Puff Daddy” Combs fathered another woman’s baby—that child was born five months before the twins.

What made it worse was that Porter first found out about his affair from some­one else. “I would have pre­ferred to find out from him because that’s a man,” she told Peo­ple, adding that although it would have been hard, she would’ve been able to get past it. “Even if I couldn’t have under­stood it as a woman, I would have under­stood it as a friend.”

Combs even­tu­ally left both women behind and was linked to a string of younger women, before finally set­tling down with singer Cassie Ven­tura. The celebrity cou­ple is rumored to have started dat­ing back in 2007, but didn’t really con­firm their May-December rela­tion­ship till 2012.

The celebrity cou­ple sparked rumors that they were head­ing for mar­riage in early 2014 when Combs posted a pic­ture on Insta­gram of a dia­mond ring with the cap­tion, “Baby do you like it? I just want to get you wat you Like ! I just wanna Mk you smile [sic].” Although Cassie Ven­tura was spot­ted wear­ing the same ring on that fin­ger, his rep denied that the celebrity cou­ple was engaged; the ring was just an extrav­a­gant gift for his younger woman.


“Hip Hop’s Wealth­i­est Artists 2013,” Forbes web site;, last accessed April 3, 2014.

Nes­sif, B., “Sean ‘Diddy’ Combs Not Engaged to Cassie Ven­tura Despite Mas­sive Dia­mond Ring He Gave Her,” E! News web site, Feb­ru­ary 3, 2014;

Sil­ver­man, S.M., “Kim Porter Says She Was Betrayed By Diddy,” Peo­ple web site, Sep­tem­ber 10, 2007;

Photo Credit: Fea­ture­flash /