The Most Tragic Details About Britney And Jamie Lynn Spears' Strained Relationship

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It's no secret that sisters Britney Spears and Jamie Lynn Spears have shared a contentious and volatile relationship over the years. Never forget the time the "Toxic" singer tore down Jamie Lynn's career in an epic rant, or the time Jamie Lynn opened up about her scariest incidents with Britney in her book, which ultimately resulted in Britney's legal team sending Jamie Lynn a cease-and-desist letter. YIKES.

Sadly, the bitter fallout between Britney and Jamie Lynn just keeps getting worse. On October 16, Us Weekly reported that Kevin Federline's upcoming memoir, "You Thought You Knew," contained details of private text messages in which Jamie Lynn thanked both Federline and his wife, Victoria Prince, for "raising" Britney and Federline's teenage sons, Sean Preston and Jayden James. Unfortunately, that's just the tip of the iceberg when it comes to the high-profile sisters' estranged relationship. Let's take a look back, shall we?

In the confines of her 2023 tell-all memoir, "The Woman In Me," Britney Spears revealed that she and her younger sister, Jamie Lynn Spears, have been at odds with one another since childhood. "My little sister — well, when I tell you she was a total b***h, I'm not exaggerating," Britney wrote. "It was clear that girl ruled the roost. Meanwhile, it was like I was a ghost child. I can remember walking into the room and feeling like no one even saw me. Jamie Lynn only saw the TV." Britney went on to say that Jamie Lynn was also ungrateful for the family home Britney bought for Jamie Lynn and the rest of the family to live in. "She'd later say, 'Why'd she get us a house?' — like it was some sort of imposition," Britney wrote. 

Britney also recalled a moment when she showed up on set to confront Jamie Lynn's "Zoey 101" co-star Alexa Nikolas after Jamie Lynn had claimed Nikolas was bullying her. In the book, Spears said she later found out that Jamie Lynn had made the whole thing up. "What I must have looked like, hugely pregnant, yelling at a teenage (and, I would later learn, innocent) girl," Britney dished about the incident.

Jamie Lynn Spears, however, has a very different recollection of growing up with Britney Spears. In her 2022 memoir, "Things I Should Have Said," she credits Britney with helping to raise her. "Being the baby sister of Britney Spears is nothing like what people assume. From the day I arrived, I became Britney's. Momma was often working and taking care of the family. She was also dealing with the complexities of an addict husband," Jamie Lynn recalled, per ET Online.

According to Jamie Lynn, it wasn't until Britney's high-profile split with Justin Timberlake that things became strained between the sisters. "The constancy of their relationship provided the best example of a loving couple I had ever seen," Jamie Lynn confessed. "I was completely heartbroken when it was over and believed that it was a devastating loss in Britney's life as well." Jamie Lynn went on to share that in the aftermath of Britney's breakup with Justin, Britney started to pull away from her. "After years of making me a priority and spending time together, my sister was now moving on without me," she wrote. Case in point: Britney's erratic decision to marry family friend Jason Alexander during a wild night out in Las Vegas. "I just knew this was a bad idea. Something was way off with her," Jamie Lynn recalled. "The last thing I said before she left was, 'Now don't go and marry Jason while you're there, Britney!' She rolled her eyes at me and said the equivalent of 'as if.' But sure enough, within hours we got word that in a haze of substance she had married him."

In May 2017, Jamie Lynn Spears surprised her sister at the Radio Disney Music Awards, presenting her with the first-ever Icon Award and paying tribute to her via a remix performance of all of Britney's top hits. Unfortunately, while Britney appeared to relish the award and performance at the time, even hamming it up in front of the audience and cameras, she later revealed that she was hurt by it. "I don't like that my sister showed up at an awards show and performed MY SONGS to remixes!!!!! My so-called support system hurt me deeply," she confessed in an Instagram post on July 17, 2021. "This conservatorship killed my dreams ... so all I have is hope and hope is the only thing in this world that is very hard to kill ... yet people still try."

Jamie Lynn later said during a January 2022 interview on "Good Morning America" that she was "confused" by Britney's claims that the performance had hurt her. "I was doing a tribute to honor my sister and all the amazing things that she's done," she said. When asked whether Jamie Lynn had cleared all of that up with Britney, Jamie Lynn answered, "I have cleared up with the fact that I don't think she's personally upset with me about that."

In the confines of her book "The Woman in Me," Britney Spears has alleged that her sister, Jamie Lynn Spears, did nothing to help her escape her conservatorship and rehabilitation stays. Instead, Britney claimed that Jamie Lynn simply told her to "stop fighting it." Britney lamented, "I felt like she should have taken my side."

According to Jamie Lynn, however, she did, in fact, try to help Britney as it pertained to the conservatorship. During an appearance on "Good Morning America" in January 2022, Jamie Lynn told ABC News anchor Juju Chang that she did what she could to help Britney get out of the conservatorship, even ensuring that Britney "had the contacts she needed to possibly go ahead and end this conservatorship." She also maintained that she was "happy" once Britney's conservatorship had ended. When pressed as to whether or not she disagreed with the conservatorship, Jamie Lynn maintained that "it wasn't about agreeing with the conservatorship." Jamie Lynn added, "Everyone has a voice and it should be heard."

Perhaps Britney Spears and Jamie Lynn Spears' estranged relationship really boils down to one million-dollar question: Did Jamie Lynn ever get any of Britney's money while Britney was under the conservatorship? While the New York Times reported in June 2021 that Britney paid her and Jamie Lynn's father, Jamie Spears, a whopping $16,000 a month for more than 12 years, it's often been rumored that Jamie Lynn also financially benefited from her sister's fortune during that time. Meanwhile, Britney hasn't exactly helped quash those rumors. "My family has lived off my conservatorship for 13 years," she famously testified in court in June 2021 (via Variety) — heavy emphasis on the word "family" and not "father."

Jamie Lynn has vehemently denied ever being on her sister's payroll. During an appearance on "Good Morning America" in January 2022, Jamie claimed that there "was a time" Britney came to her and asked if she would be the one to ensure that Britney's sons Sean Preston and Jayden James "got what they needed." But according to Jamie Lynn, she ultimately opted not to get involved, citing Britney's conservatorship as the reason. "I felt like I just didn't want to be a part of until maybe she was out of the conservatorship," she explained. "There was no like me overseeing funds or something like that. And if that was, it was a misunderstanding. But either way, I took no steps to be a part of it," she declared. According to documents obtained by The Blast, however, Jamie Lynn was named as a trustee in the SJB Revocable Trust in 2018 — a trust that was first created by Britney in 2004.