Shar Jackson Always Praised Kevin Federline’s Parenting Despite Their Personal Drama

Former backup dancer Kevin Federline has done a lot of living. I mean, few can gloat about having not one, but two famous baby mamas, though everyone doesn’t have Kevin’s rizz, but I digress.

Kevin famously married Britney Spears in 2004, with whom he shares children Sean Preston and Jayden James. However, ‘90s babies (and those who were raised right) know that before Britney, he had several older kids with his ex-fiancée, actor and Moesha star Shar Jackson.

Kevin and Shar’s tumultuous relationship became tabloid fodder during his and the “Baby One More Time” singer’s courtship. Fortunately, the two discovered they’re a better fit as co-parents.

Here’s a look at the family Shar and Kevin built.

Shar and Kevin’s relationship began sometime in the early 2000s. In 2002, they welcomed their first child together, Kori Madison Jackson Federline. According to People, Kori was Kevin’s firstborn and Shar’s third. The Good Burger star was already a mother to two children from a previous relationship, Donavan and Cassalei Jackson. Two years after Kori’s birth, Shar and Kevin welcomed their second child, Kaleb Michael Jackson Federline, in 2004.

Although both Kori and Kaleb have been spotted on the red carpet or by paparazzi with their mom or dad, they seem to lead private lives, something that Shar wanted for them. She decided to take a break from the entertainment industry to focus on raising her children. Shar credited Kevin for making their family work even after their romantic relationship ended.

“He’s an amazing dad,” she shared with People in 2006. “When Kori was first born, her whole first year and a half, he was there. I mean, he wouldn’t leave her side. He’s a good guy, and when he’s not with [his kids], it hurts his heart that he misses them so much.”

Kevin and Shar’s relationship ended while she was pregnant with their child, Kaleb. According to his 2025 memoir, You Thought You Knew, he started sneaking around with Britney during Shar’s pregnancy. After a period of keeping his affair under wraps, Kevin later confessed to cheating and falling in love with Britney, and ultimately broke up with Shar over the phone.

"I could hear the heartbreak in her voice, and the pain it caused," he wrote. "She was angry. But under the anger was something deeper, a sadness I couldn't undo."

Kevin and Britney married on Oct. 6, 2004, three months after his and Shar’s youngest’s birth. They soon welcomed Sean Preston in 2006, followed by Jayden James in 2006. In the years since they all parted ways romantically, Kevin revealed in his memoir that he would “handle that whole thing differently.”

Fortunately, Shar shared soon after Kevin and Britney’s sons were born that all of the adults involved tried to keep their kids connected as much as possible. Kevin has also posted multiple photos of himself with all of his children.