Britney Spears and ex-husband Kevin Federline welcomed their first child, Sean Preston Federline, in 2005
Spears welcomed Sean Preston with her then-husband Kevin Federline on Sept. 14, 2005, and his little brother Jayden James Federline joined the family almost exactly a year later on Sept. 12, 2006. While Spears admitted to PEOPLE in 2017 that “the balance between work and my personal life can be a challenge,” she still made sure to put her son “first, always.”
Spears filed for divorce from Federline in November 2006, but they worked hard to co-parent as peacefully as possible, sharing varying levels of custody through the years. “I always do my best to plan my schedule around my family whenever possible,” she told PEOPLE in 2017.
Nowadays, the boys spend most of their time with their dad, but stay in touch with Spears. “I have to ask their permission to post them [on Instagram] because they are extremely independent little men,” she shared in a birthday post to her sons in 2021.
Federline also supports Spears and Sean Preston remaining close. "The best thing would be for their mom to be healthy and happy,” Federline’s lawyer told PEOPLE in 2021 amid Spears’ conservatorship case. "[Kevin] certainly respects Britney and only hopes the best for her ... The kids love their mother and he wants there to be a healthy and strong relationship."
For her part, Spears says “starting a family was [her] dream come true,” and she was willing to do anything to stay close with her sons, including staying in a conservatorship for 13 years.
“My freedom in exchange for naps with my children — it was a trade I was willing to make,” she wrote in her memoir The Woman in Me. “And so I went along with it.”
Here’s everything to know about Britney Spears and Kevin Federline’s older son, Sean Preston Federline.
Sean Preston was born in September 2005
Spears and Federline welcomed their first child, son Sean Preston, on Sept. 14, 2005, at Santa Monica UCLA Medical Center. Spears’ mom Lynn Spears and sister Jamie Lynn Spears were there to support the popstar as she planned for a scheduled C-Section, but ended up going into labor a day before.
"We are ecstatic to announce the birth of our son!” the former couple said in a statement to PEOPLE at the time. “Everyone is happy, healthy and doing wonderful. Thank you all for your love and well wishes!" Sean Preston was 6 lbs. 11 oz., and the pair brought him home to their newly renovated estate in Malibu, CA.
In 2021, Spears opened up about being a “very young” mom. "I had my babies very young … at all the pools we went to on tours, all the babies flocked to me because I always brought the most toys,” she shared on Instagram.
He has 5 brothers and sisters
Sean Preston is one of six children on his father’s side, and he was born in the middle of the pack. Federline has two kids — daughter Kori Madison and son Kaleb Michae — with his ex-fiancée Shar Jackson. He then welcomed Sean Preston and his brother Jayden with Spears before becoming a dad to two daughters, Jordan Kay and Peyton Marie, whom he shares with his wife, Victoria Prince.
"You fall into your routine and it's really easy now," he said of his blended family on Bravo's Personal Space in June 2017. "It wasn't always easy, but it's a lot easier now." Despite feeling like he’s “trying to control a basketball team,” Federline is proud that his kids are all “great” and all “get along” with each other.
He accompanied his mom to red carpets at a young age
Considering his mom was already one of the biggest stars in the world when he was born, Sean Preston was in the spotlight at an early age, and attended his fair share of major celebrity events.
A few years later, Sean Preston even joined Spears on her Piece of Me Tour in 2018. “They’re such sweethearts,” she told PEOPLE of the boys. “I love them to death. It’s the greatest gift being a mother.”
He was "very expressive" as a child
Spears loved watching her boys grow into “little men" and develop their personalities.
“Preston is very opinionated, very expressive, and if he doesn't like something, he’s going to tell you,” she told PEOPLE of her older son in 2015. “But he has a huge heart, he’s a good kid, and he has manners. It’s been enlightening for me to see him growing and changing.”
When Sean Preston was little, Federline told PEOPLE that he had a “sensitive” personality. “His feelings get hurt real easily,” he said. “He is the one that is always under my wing; he doesn’t want to go anywhere without Daddy."
Sean Preston has lots of hobbies and interests
Sean Preston has had a lot of passions in his young life, from DJing to dreaming of becoming “a race-car driver,” as his dad told PEOPLE. One thing is for sure — he loves staying active.
“[Sean Preston] plays football,” Spears told PEOPLE in 2018. “It’s so funny because he’s kind of tiny so I worry about them being out there with all their gear and all that kind of stuff ’cause they actually tackle each other … To me, he’s still a baby so I’m like ‘Please stop!' ” Still, she said she “loves” watching him play.
He’s even more passionate about skateboarding. “After school sometimes they’ll go to gymnastics, which they love,” the "Gimme More" singer told PEOPLE in 2015. “Or I take them to the skate park. They’re obsessed. We have a half-pipe at the house.”
That same year, she posted a photo throwing up peace signs with the boys holding skateboards, captioning the snap, “Just your typical proud skate mom.”
He loves music like his parents
With a popstar mom and a DJ and dancer dad, it’s really no surprise that Sean Preston would fall in love with music. In 2015, he tried his hand at DJing like his father. “He’s in there working hard,” Federline told PEOPLE in August 2015. “It’s so funny to watch. He’s 9 years old, about to be 10, and probably by the time he’s 12 he’ll be really, really good."
While Federline showed his son a few tricks, he’d rather see him “figure it out on his own.” “He’s got a good ear, he really does. It will be interesting to see where he’s at in a couple of years.”
In 2018, Spears shared a video of Sean Preston playing piano with the caption, “A few weeks ago, my son sat down and started playing our piano. He’s never had a lesson a day in his life, so needless to say I started tearing up like a proud mom! My baby is like a lil Mozart!”
However, the "Circus" singer wasn't always thrilled at the idea of her kids joining the music industry, telling PEOPLE she would “try to steer them away" — unless they really had a passion for it.
“It’s about what that little person wants for their life, you know?” she said.
Sean Preston has had ups and downs with his mom
In August 2022, Federline told Daily Mail that his sons hadn’t seen Spears in “a few months” and “have decided they are not seeing her right now” after Spears posted photos of them online. “It's tough. I can't imagine how it feels to be a teenager having to go to high school,” he said of the situation.
Jayden echoed his dad's sentiments in his own interview, saying Sean Preston “asked my mother not to post his photos, and she did it anyway. So it didn't go well."
Spears was frustrated by the situation, and took to Instagram in a now-deleted post to air her grievances, saying she was also taking time away from communicating with her family. "I'm afraid to inform you guys, I'm not willing to see you until I feel valued," she said.
"My love for my children has no boundaries and it deeply saddens me to know his outcry of saying I wasn't up to his expectations of a mother," she added in an earlier post. "Maybe one day we can meet face to face and talk about this openly!"
He did not attend Spears’ wedding to Sam Asghari
In June 2022, Spears married her now-ex Sam Asghari at her California home. While Sean Preston and Jayden did not attend the nuptials, they wished their mom well. "They're happy for their mom and they are hopeful that Sam and Britney are starting a great future together," Mark Vincent Kaplan, Federline's longtime attorney, told PEOPLE ahead of the event. "It's their night and they didn't want to take away from them."
Jayden further elaborated on their absence to the Daily Mail in September 2022. "At the time it just wasn't a good time to go,” he said. “I'm not saying that I'm not happy for her. I'm really happy for them, but she didn't invite the whole family, and then if it was just going to be me and Sean Preston, I just don't see how that situation would have ended on good terms.”
He also has a complicated relationship with his grandfather, Jamie Spears
Federline sought a protection order from the courts in 2019 after Jamie Spears allegedly got into a physical altercation with Sean Preston when he was 13 years old and his mom was still under her conservatorship.
Though Sean Preston discontinued contact with his grandfather, his dad would be open to them reconciling. "I would absolutely welcome Jamie Spears back in the boys' lives,” he told Daily Mail in 2022. “Especially if that's what the boys wanted. I don't have any hard feelings towards Jamie Spears. People make mistakes. I feel bad for him. I feel like he's been put through the wringer."
For his part, Jamie “misses” his grandson “really, really bad.” “We were very, very close," he told Daily Mail. "It's been a tough three years without them. The family's a mess. All we can do is keep praying."
Sean Preston currently lives in Hawaii with his dad
In 2023, Federline and his wife made the decision to move to Hawaii with their family to pursue professional opportunities. Federline reached out directly to Spears for permission, and the singer "consented" to her children's relocation.
"It's an opportunity for Kevin and his wife, and the boys are ready to get away from the L.A. microscope," Kaplan told PEOPLE.
"Britney has always faithfully supported her children and wants them to be happy," a source told PEOPLE at the time.
The move was set to happen in the summer after Sean Preston graduated from high school. A few weeks after Spears agreed to Federline's request, she shared a sweet throwback photo of her older son on Instagram.
“My first love!!!” she captioned the post.
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