Inside Britney Spears' Relationship With Her Family Today

Britney Spears was just 16 years old when her first single, "...Baby One More Time" was released in the U.S. This song did more than launch the career of a pop star — it was the beginning of a journey that changed pop music as we know it. That was over 20 years ago. As of this writing, Spears is a 39-year old mom of two who released her latest studio album, 2016's Glory more than four years ago.

Spears' life has changed considerably since she topped the charts and toured the world in the late 90s and early aughts. She's had an annulment, a divorce, and she's been living under a legal conservatorship since 2008. As Spears' life has changed, so has her relationship with her family members. Spears is so far out of the public eye that details about her day-to-day life are scarce. But we're digging deep to take a look inside Britney Spears' relationship with her family today.

Britney Spears has been under a legal conservatorship since 2008. Per California court's Handbook for Conservators, a conservator is "an individual or organization chosen to protect and manage the personal care or finances—or both—of a person who has been found by a judge or a jury to be unable to manage his or her own affairs." Britney's father, James "Jamie" Spears became her conservator following a temporary arrangement that was eventually "made permanent" after Britney was hospitalized for several psychiatric incidents, per Los Angeles Times. 

Britney's fans quickly made their opposition to the conservatorship known, with The Washington Post reporting that the phrase "Free Britney" first appeared online in 2009. Since then, Britney has been taking legal steps to make changes to the arrangement, including a successful February 2021 petition to have a co-conservator, Bessemer Trust, added, per NPR.  

While Britney hasn't publicly spoken out herself against her father or his oversight role in her life, her lawyer has stated (via Los Angeles Times) that "at this point in her life ... she is trying to regain some measure of personal autonomy." He also made it clear that Britney did not want her legal proceedings regarding her conservatorship sealed, and "vehemently opposed" what she views as father's apparent actions "to keep her legal struggle hidden away in the closet as a family secret." 

Britney Spears' father Jamie Spears allegedly wasn't involved much in his daughter's life before the legal conservatorship, per sources in Hulu's "Framing Britney Spears" episode of The New York Times Presents. When Britney was auditioning in New York as a youngster, her mom Lynne Spears, lived with her. Britney's former talent agent, Nancy Carson, said that while Lynne was very proud of Britney, Jamie, "was more concerned with the financial aspect of it. How was he going to be able to make [fame] happen?"

When Britney got her record deal, Lynne had to take care of Britney's sister, Jamie Lynn Spears, in Louisiana. She hired friend Felicia Culotta as Britney's chaperone. "Britney's father wasn't around very much when Britney was growing up," Liz Day, a senior editor at The New York Times said on the episode, adding that "Jamie was struggling with alcohol," went "to rehab," and couldn't keep a job. Day also revealed that Jamie "fil[ed] for bankruptcy" after a failed business venture. During a 2019 court hearing (via US Weekly), Jamie's even confessed during testimony, "Me and my daughter's relationship has always been strained."

Former senior director of marketing at Britney's label Jive Records, Kim Kaiman, also claimed in the documentary episode that while Lynne was supportive of Britney, "The only thing Jamie ever said to me was, 'my daughter's gonna be so rich, she's gonna buy me a boat.'" 

Jamie Spears had his daughter's well-being in mind when he was legally named Britney Spears' conservator in 2008. She'd had psychological breakdowns, and there were people in her life who were allegedly taking advantage of her, including Sam Lutfi, who falsely claimed to be her manager. In her book Through The Storm (via the New York Post), Lynne Spears accused Lutfi of manipulating the pop star with drugs and psychological abuse, and described him as a "gatekeeper," who "wanted to keep the gate closed to more than Britney's family." 

Jamie was instrumental in helping Britney win restraining orders against Lutfi in both 2009 and 2019, according to CNN, but somewhere along the way, his own control over her life crossed a line for Britney. In 2020, the Los Angeles Times reported that Britney started legal efforts to fully remove her father as conservator, going so far as to claim (through her lawyer) "that she is afraid of her father." She also refused to "perform as long as her father is in charge of her career." Jamie, the outlet separately reported, has "aggressively contested" Britney's moves in court. 

Jamie told CNN in December 2020 that he hadn't spoken to Britney since August 2020. "I love my daughter and I miss her very much," he said, adding, "When a family member needs special care and protection, families need to step up, as I have done for the last 12-plus years, to safeguard, protect and continue to love Britney unconditionally."

Britney Spears had her oldest son, Sean Preston Federline, on Sept. 14, 2005. Jayden James Federline was born soon after on Sept. 12, 2006. She divorced their dad, Kevin Federline, in July 2007, and shared "equal custody" of the boys thereafter, per Us Weekly's timeline of their relationship. Following the "Lucky" singer's public struggles with her mental health, Kevin won full custody of Sean and Jayden in 2008. Britney's custody was adjusted to visitation with the boys two days and "one overnight per week." Kevin reportedly allowed the visitation schedule to be flexible until August 2019, when Britney received 30 percent custodial rights with Kevin getting the remaining 70 percent.

In September 2019, Kevin reported Jamie Spears to police after the elder Spears allegedly broke down a door during an argument with Sean and "shook [him]" via Us Weekly. TMZ reported that there were no marks on the boy and no charges were filed, per Radar Online. The incident reportedly caused further strain between Britney and her father, or as a source told Us Weekly: "[Jamie] is the reason she has far less custodial time with her sons than she did before."

In March 2020, Britney's son Jayden did an Instagram live, calling his mom "legendary," saying he saw her "two days ago," and would see her again in "a couple weeks." He also called Jamie some choice words. His account has since been deleted.

Since their divorce was finalized in July 2007, Britney Spears' ex-husband, Kevin Federline, has allegedly been understanding when it comes to giving Spears visitation with her sons. But they have had arguments. Per Us Weekly, a source said "they kept their distance from one another and didn't speak at Sean Preston's Little League game in 2011. The exact reason was not reported. They were on speaking terms again by 2013 (via Us Weekly), but in 2018, things got rough again when Federline requested more child support from Spears, Us Weekly reported. The former couple agreed that Spears would increase her child support payments from $20 thousand a month to about $35 thousand per month.

Federline has always been supportive of Spears' goal to improve her mental health. He has stayed out of Britney's conservatorship issues, but released a statement through his lawyer (via E!), saying that Jodi Montgomery, who took over as Britney's conservator in her personal life in 2019, has "done an admirable job."

As the Los Angeles Times pointed out, Britney's conservatorship is two-fold, with oversight over both her personal and professional lives. Jamie was initially conservator over both until September 2019, when he stepped down from the personal side, citing his health. The tabloids, however, noted this change occurred shortly after Jamie was accused of a physical altercation with Sean Preston.

When Britney Spears was at the height of her fame, Lynne Spears appeared to be at her eldest daughter's side as much as possible. The "Stronger" singer and her mom even wrote a book together in 2000, called Britney Spears' Heart To Heart, in which the duo "share intimate details about Britney's rise to stardom," per Amazon. They also share insight into having a successful mother-daughter relationship with readers.

But it wasn't always that way. While promoting her 2008 book, Through The Storm, Lynne told Daily Mail, "When her life was such a success, what did she need me for? And when things took a turn for the worse, I was out, because other people – dancers, managers – were closer to her, and with her day and night." Lynne is referencing the period of time that Britney acted erratically in public and lost custody of her sons. "Being a mother, you can't help but have regrets about what you did and didn't do for your kids, and I'm no different." 

Lynne stayed out of the legal issues regarding Britney's conservatorship for years, perhaps preferring to give her daughter emotional support. But in May 2019, Lynne "requested special notice of all matters relating to Britney's conservatorship" (via ET). She started making court appearances with Britney, and, in July 2020, she filed a petition (obtained by Blast) to be involved in "all decisions made" about the trust that holds most of the "Toxic" singer's fortune. 

Britney Spears' younger sister, Jamie Lynn Spears, has had her own difficulties in the spotlight. She was 16 when she got pregnant with her daughter Maddie and took a break from acting to move back to Louisiana. The Sweet Magnolias actor told The Hollywood Reporter in May 2020 that her sister has always been in her corner. "Having Britney as an example was crucial for me. Not only did my sister build me up, but she made me feel like I was the star when she was clearly the star." She called the "Lucky" singer's advice her "secret weapon."

Jamie Lynn loves having a sister who is a "living legend" with "a legacy that will last forever," telling THR, "I'm so proud of Britney for everything that she's been able to accomplish and the impact she's had, not just on pop music but the industry as a whole."

The sisters seem close. Jamie Lynn even became "trustee of [Britney's] multimillion-dollar estate" in 2018 (via Los Angeles Times). But Jamie Lynn has to defend their bond on social media. When she made a joke about a picture of Britney and her ex, Justin Timberlake, on Nylon's Instagram account, fans got defensive and Jamie Lynn had to clarify (via Hello!), "I talk with my sis and also make comments I find funny on Instagram. Strangely, I'm capable of doing both ha."

Big brother Bryan Spears (pictured above) is almost four years older Britney Spears. He has not pursued a career in the spotlight like his sisters, but he is a trustee of one of Britney's trusts, and received $200 thousand dollars from her before the conservatorship was in place for "services [rendered]" per 4 NBC Washington. He was more involved in youngest sister Jamie Lynn Spears' career, serving as a producer on her hit Nickelodeon show Zoey 101 (via IMDb). He even married Jamie Lynn's former manager, Graciella Sanchez, in 2009. They have a daughter together named Sophia Alexandra Spears.

Bryan shed some light on his relationship with Britney in an interview on the As NOT Seen on TV podcast, saying he talks to Britney "constantly." He also gave some insight about how the pop star feels about the conservatorship. "She's always wanted to get out of it, it's very frustrating to have ... someone constantly tell you to do something," he admitted. Bryan also expressed concerns over Britney's ability to manage her own affairs, even as an adult, because "she's been surrounded by a team of people since she was 15." To that point, he also said he feels that his dad has "done the best he could given the situation he was put in and we've had to, like, work together as a family to keep [Britney's career] going." 

Alli Sims became her cousin Britney Spears' personal assistant in 2007. The two were often seen together, but Sims told NBC News that she had to end their relationship when Britney's father, Jamie Spears, allegedly threatened to harm her if she kept talking to Britney. "He 100 percent was threatening me with my life," Sims said in February 2021. "I didn't put it past him, so I didn't answer [her calls]."

Sims hasn't given an interview in many years, but said she was inspired to speak because of the "Framing Britney Spears" episode of The New York Times Presents. "How do you watch that documentary and be in it and live in that and not say anything when it has gone on for so long?" she said. Sims now lives in Louisiana with her husband and daughter and said she has a "lot of guilt" about not being able to help Britney. Per "Framing Britney Spears," Sims was with Britney on the night she allegedly damaged a paparazzo's car with an umbrella. "I can't imagine how alone she felt [during her hardest times]," Sims told NBC News.

"Do I miss her as a person and think about her all the time? Yes," Sims said. She hopes Britney can tell her story one day. "If she does, get ready because there's more to that story than I'm sure anybody could ever imagine."

Britney Spears met Sam Asghari on the set of her "Slumber Party" video in 2016. "I was excited that I get to meet one of the biggest artists of all time," he said. "I had butterflies," he told Men's Health. They exchanged numbers, went for sushi, and the rest can be seen on social media, where they often post videos doing workouts together. Britney told The Associated Press (via Men's Health) that her son Sean Preston Federline films the workouts and Asghari edits the videos. "[Sam] a trainer so everything has to be so perfect. We probably did 40 [takes] and I hurt myself," she joked.

Aside from their workout vids and the normal couple cuteness found on any celeb pair's social media, Asghari has also very publicly stuck up for his girlfriend. After "Framing Britney Spears" aired, he didn't even try to hide his disdain for Jamie Spears. "Now it's important for people to understand that I have zero respect for someone trying to control our relationship and constantly throwing obstacles our way," Asghari wrote in an Instagram story on Feb. 10, 2021 (via Cosmopolitan). "In my opinion James is a total d**k," he bluntly added. In an official statement to People Asghari was more diplomatic, stating, "I have always wanted nothing but the best for my better half, and will continue to support her following her dreams and creating the future she wants and deserves."