Growing up as the son of pop royalty may have sounded like a dream for some once upon a time, but as we well know, the cons often outweigh the pros by a long shot. When it comes to Sean Preston Federline, that’s certainly been the case — and sadly for Britney Spears’ eldest son, a lot of what he’s endured over the years has ended up making headlines.
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Some will recall that in early 2006, Spears came under fire after her firstborn — who has always been known by his second name, Preston — was photographed on her lap while she was driving. A dangerous move, for sure. However, Spears released a statement soon after explaining that she’d done what she did specifically because she was afraid for her son’s safety. Speaking to People, the singer shared that Preston had first been taken out of his car seat while they were in the parking lot of a Starbucks. Her bodyguard was inside the store at the time, but by the time he got back to the car, the paparazzi had arrived in droves — and Spears was terrified.
“Because of a recent incident when I was trapped in my car without my baby by a throng of paparazzi, I was terrified that this time the physically aggressive paparazzi would put both me and my baby in danger. I instinctively took measures to get my baby and me out of harm’s way, but the paparazzi continued to stalk us, and took photos of us which were sold to the media,” she told People. A traumatic situation for a new mom and baby alike, no doubt. However, things only became more heartbreaking when Spears felt a need to clarify, “I love my child and would do anything to protect him.”
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Preston was dropped by his nanny when he was a baby
Two months after Sean Preston Federline was pictured on his mom’s lap while she drove, the infant made headlines once again. This time, it was because he’d been dropped by his nanny and knocked his head.
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Of course, the fact that Preston had been dropped was concerning enough, and Star reported at the time that he had sustained a skull fracture (via China Daily). Even so (and perhaps unsurprisingly given the constant attacks on Britney Spears’ parenting at the time), the attention shifted to the fallout his mother faced in the wake of the situation. Though outlets confirmed that a doctor had gone to Spears and Kevin Federline’s home right after their son was dropped and given the then-first time parents the okay, when the couple took Preston to the hospital a few days later, concerned that he was sleeping more than usual since the fall, the press nonetheless jumped on the fact that the Department of Children and Family Services was asked to check in on the family. People even shared a comment from a reader in the know who claimed that the department being called in wasn’t a given, and that it was possible hospital staff were suspicious of the parents.
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Ultimately, People also included a statement from Spears’ lawyer, which shut down any speculation. “DCFS immediately responded and determined there was no problem and no reason to open a formal investigation … They determined that the parents were not involved in any injury and that nothing improper was done within the home,” Marty Singer said. As for the fact that a Los Angeles County sheriff’s deputy had gone with the department when it visited Spears’ home, a spokesperson for the sheriff told Star that was par for the course.
Preston’s parents’ custody battle was brutal
One particularly harrowing incident some may remember came when Sean Preston Federline was just 2 years old. At the time, Britney Spears and Kevin Federline were in the midst of a very heated custody battle, with the latter grated temporary full custody of both Preston and his 1-year-old brother, Jayden James Federline. One evening — a few hours after Spears and Kevin had been in court — the pop star was scheduled to hand her kids back to her ex. However, things infamously spiraled out of control.
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Though Preston was handed over to the third party who’d come to pick him and his brother up, Spears holed up in the bathroom with Jayden, prompting a very tense, hours-long standoff. Ultimately, Spears and Jayden emerged nearly four hours after the scheduled handover, with both mother and son placed in separate ambulances. Sadly for Spears, her troubling relationship with the paparazzi took center stage, and paps didn’t even hold back while she was en route to the hospital. In fact, incredibly disturbing footage from that night showed them banging on the vehicle and its windows all the way to Cedars-Sinai, where they were eventually forced to leave by police.
It’s not clear if Preston bore witness to any of the drama as it was unfolding. However, there’s also no question that it was a high-stress situation for anyone to be in, let alone a child who wouldn’t have understood what was going on. Spears has since written in “The Woman in Me” that on that night, she’d been overwhelmed by the possibility that she would never see her children again. Even so, as Kevin’s lawyer Mark Vincent Kaplan pointed out when speaking to The Guardian of the matter, “There’s no winners here.”
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Preston had a scary incident with his grandfather
Fast-forward more than a decade to 2019, Sean Preston Federline found himself in the headlines for another heartbreaking reason. This time, Kevin Federline accused Britney Spears’ dad of becoming violent with his eldest son. Blast reported that Britney and her sons had been at Jamie Spears’ home when Preston and his grandfather began arguing. Things escalated quickly, and Preston ran to his room. However, things only intensified from there, and Jamie not only broke the door down, but shook his grandson once he’d gained access.
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Speaking to People of the situation, Kevin’s lawyer confirmed that an argument had turned physical, and in a sign of how much his client’s and Britney’s relationship had improved in the years since their divorce, even commended the singer for getting her kids out of the situation as fast as she could and calling her ex to take them home. That said, Mark Vincent Kaplan once again pointed out that the ordeal had been distressing for the children. “The trauma to the kids is nonetheless,” he said. Kevin filed a police report the following day.
In the years since, Preston and Jamie have made up. In fact, in a 2024 report by TMZ, insiders claimed both Preston and his brother spoke with their grandfather fairly regularly, and even wanted to see him IRL. Likewise, speaking to Page Six a few days later, Kaplan confirmed that to be the case. “The boys miss their grandfather. They have forgiven him,” he told the outlet.
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Jayden says Britney was stricter on Preston
While Sean Preston Federline has tended to prefer keeping a low profile over the years, Jayden James Federline has been a little more forthcoming — and in a 2022 interview with ITV, Britney Spears’ youngest child opened up about life with their mom. He also shared that Spears had been way stricter with Preston than she’d ever been with him.
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“I think mom has struggled giving us both attention and showing us equal love and I don’t think she showed enough to Preston and I feel really bad for that. We’ve both been through so much pressure in the past that this is our safe place now, to process all the emotional trauma we’ve been through to heal, heal our mental state,” Jayden James Federline told ITV (via Daily Mail). Jayden added, “If I complained, she went after him. … I feel guilty, so I am there for him.”
It does bear mentioning that even if Spears was harder on her older son, Kevin Federline (who has four other kids aside from his sons with Spears) seems to have been much milder across the board. Many years back, Kevin actually told People that Preston was the more sensitive of his and Spears’ kids, adding, “He is the one that is always under my wing; he doesn’t want to go anywhere without daddy.”
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Preston was upset when his mom shared his pictures online
Perhaps unsurprisingly given some of the earliest moments of his life, Sean Preston Federline has made it clear he doesn’t want to live a public life. In fact, Daphne Barak, the journalist behind the ITV interview with Preston and his brother, wrote for Daily Mail that it was only once the cameras were off that he felt comfortable opening up about his life.
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One of the key things he did share? The fact that he’d felt uncomfortable when his mom posted pictures of him to social media. That’s something Jayden shared as well. “[Preston] doesn’t like the cameras. He asked my mother not to post his photos, and she did it anyway. So it didn’t go well,” he shared. Preston is said to feel anxious about having even his own social media, so we’re not shocked to hear that.
As many will know, Britney Spears’ kids chose to end their relationship with her for a time after her conservatorship came to an end. That said, 2025 seems to have been a turning point, at least for Jayden, who has hung out with his mom and even let her share snaps of their time together on social media. It’s not clear if both kids repaired their relationship with Spears, or if Preston has been in attendance for any other hangs. However, that in itself could be a good sign: Perhaps Spears is just committed to honoring his no-photos policy. Either way, we’re wishing him nothing but the best — and if he chooses to stay out of the spotlight for the rest of his life, we’ll certainly understand why.
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