How Kevin Federline And His Wife Landed In Legal Trouble Together

Kevin Federline isn't exactly known for being a Boy Scout. From the time he started dating Britney Spears, he quickly gained a reputation for being a bad boy. The story goes that Federline and Spears purportedly met at a club in Hollywood, all while his then-girlfriend, actor Shar Jackson, was pregnant with their second child. "He cheated, he lied, he left. There you go, in that order," Jackson told MTV News in 2005 about the demise of their relationship and the synchronous beginning of Federline and Spears' romance.

Since then, all parties have moved on, and Jackson and Spears appear to get along swimmingly. Meanwhile, Federline met Victoria Prince in 2008, and by 2013, the couple had tied the knot. The new Mr. and Mrs. Federline expanded their family by two with the birth of their daughters: Jordan Kay in August 2011 and Peyton Marie in August 2014. All in all, this brought Kevin's brood to a grand total of six, but who's counting?!

In May 2023, however, Federline raised eyebrows once more when it was revealed he and Prince were planning on relocating the family — including he and Spears' shared sons Sean Preston and Jayden James — to Hawaii. "It's an opportunity for Kevin and his wife, and the boys are ready to get away from the L.A. microscope," Federline's attorney, Vincent Kaplan, told People. But as it turns out, the move actually played a role in landing the married couple in some legal trouble.

The couple was sued for an unpaid private school tuition bill

Ahead of their August 1 move to The Big Island, Kevin Federline and his wife, Victoria Prince, were slapped with a hefty lawsuit for an unpaid private school tuition bill. According to court documents obtained by TMZ, the couple was sued by their daughters' former school, West Valley Christian School, for "failing to pay for services which had been provided on credit at their special instance and request." It was reported that the school sought a total of $15,593 plus 10% interest on the unpaid debt that goes as far back as May 2019. Ruh roh.

According to West Valley Christian School's official website, the school's mission is "to provide excellence in education to our students, and to inspire each one of them to seek Christ and His Kingdom." Per their current tuition rates, parents of first through fifth graders can expect to pay $9,700 per year per child. The cost rises to $10,800 per year per child for grades sixth through eighth. 

The lawsuit was ultimately dropped

All's well that ends well? In a rather curious turn of events, West Valley Christian School suddenly dropped its lawsuit against Kevin Federline and Victoria Prince in August. As evidenced by court documents obtained by Page Six, attorney Ron Chow, who represented the private school in the lawsuit, filed the dismissal "with prejudice," which is fancy attorney speak for saying the plaintiff can't ever file the lawsuit again — quite literally the opposite of Federline's ex-wife's famous "Baby One More Time" bop. 

However, It should be noted that it is entirely unknown why the lawsuit was abruptly dropped. Is it possible that Federline and Prince forked over money to cover the tuition debt? Or was it all simply one big misunderstanding to begin with? Either way, it appears Federline is once again all "Caught Up," à la the single from his one and only rap album circa 2006.