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(Apologies in advance. The tone of this article will have some bite for reasons that become clear as the story plays out)

November 12th 2021 was a very important day in the life of Britney Spears. It was on this day that a judge formally terminated the conservatorship that had been in place since Britney’s father, Jamie Spears, petitioned the court and was named co-conservator on February 8th 2008.

The end of the conservatorship meant that Britney was free to do whatever she wanted whenever she wanted with whomever she wanted in her personal and professional life. No longer was she beholden to her father or anyone else. This had to be a great thing. Yes? Not exactly.

In short order, she posted strange Instagram videos of herself wearing skimpy outfits and doing weird dances. She got pregnant by longtime boyfriend Sam Asghari whom she had dated since 2016. She suffered a miscarriage. She tied the knot with Sam. She assaulted Sam (which was reported in TMZ by ‘sources’ as an ongoing problem). She got divorced from Sam fourteen months after getting married to him. She played with what looked like real knives in a video. Her ex-husband got 100% custody of their two sons and fled to Hawaii to get as far away as financially, affordably possible. She cut off all communications with her immediate family. She wrote a book detailing the dark side of her life, which brought on a whole new set of problems for her and everyone that she torched in the book. A video surfaced of what appeared to be Britney in a restaurant talking to herself.

The post-conservatorship era sounds pretty bad. It must have been a lot worse when the Conservatorship was still active. Yes? Not exactly.

Britney still had at least ‘30% of the time’ custody of her kids. She had a relationship, albeit strained, with her family. She had Sam as her boyfriend. She didn’t (wasn’t allowed to??) get pregnant. She released some albums. She appeared as a guest judge on X factor. She did a successful residency in Vegas. She was slated to do more shows in Vegas but canceled because of mental issues brought on her father’s seriously illness. She challenged the conservatorship in 2019 and Jamie temporarily stepped down, but it was not terminated by the judge out of valid mental health concerns as related to Britney.

…which begs the question: Who thought it was a good idea, given Britney’s publicly and privately known mental health struggles, to put her in a position to fail?

In our opinion, it was Matthew Rosengart.

Rosengart is a very successful (former) federal prosecutor and trial attorney. He has represented a lot of high-profile clients who felt they were screwed out of money or defamed (Sean Penn). He has a perfect record when it comes to trials/settlements because he has a ‘burn down the house’ mentality and weaponizes the media to fire bombastic claims at whoever his client is suing.

Britney met Rosengart in 2020/early 2021.  She had expressed a desire to terminate the conservatorship because it was oppressive, illegal, it violated her personal rights, it reduced her to something that wasn’t human. She wasn’t allowed to get married. She wasn’t allowed to get pregnant.  There was also a documentary in the works about this very topic…and someone at some point pushed the two of these people together.

Some backstory on conservatorships in general is important before we circle back to Rosengart.

99% of the time, conservatorships are about family. A family member (usually on the older/elderly side) is incapable of handling his/her own affairs (some or all) and another family member or close friend/business associate is approved by the court to make those decisions. Courts do not approve or terminate these legal relationships without a thorough vetting of every possible fact and medical evaluation because there is so much sensitivity and history between those who are affected.

Invariably, over the course of time, if there is money involved (or sometimes, visitation rights (or both)), the non-conservators want access. The playbook that every litigator follows is to throw the kitchen sink at the conservator in an effort to get him/her replaced and/or the conservatorship terminated regardless of what is true and what is fiction. Words like fraud/negligence/self-dealing/battery/overstepping authority/terrible treatment/dictator/bullying/oppressive/unconstitutional. Do these fighting words sound familiar?

Rosengart loved the playbook because it played to his strengths. Blow up the other side because it’s a white hat fighting a black hat…except that he failed to recognize there were shades of gray all over the place. There was an existing (albeit dysfunctional) family unit still intact. There was an ex-husband/father and children involved. It wasn’t a kid overseeing a parent. It was the reverse. It wasn’t a kid trying to get a piece of the parent’s financial action. It was a kid having the money and the older person managing and paying himself (paying too much? To whom? Worthy of arguments in front of a judge. Agreed). It wasn’t a kid claiming that the parent was being abused. It was the kid claiming to be abused by the parent. It wasn’t a kid being kept at arm’s length from the parent. It was a kid with a dependent need for help from the trusted parent (before the kid suddenly didn’t trust the parent for reasons that only Britney and her inner circle know).

Which brings us to what Not Deadline considers the primary trait of a Hall of Fame litigator. Like a Triple Crown winning jockey, the H.O.F. litigator has several gears at their disposal to not just win the race, but to the keep horse healthily intact. They know when it’s time to sprint, when to run, when to trot, when to walk, and when to not race at all.

Rosengart believed it was always time to sprint and that cost his client (and immediate family and her friends and others) dearly.

He maneuvered to block requisite psychological evaluations. He maneuvered to block anyone in Jamie Spears’ camp from asking Britney questions in a formal setting. He maneuvered to stoke the public’s outrage by throwing gasoline on a spreading fire known as the ‘free Britney’ movement. He publicly accused Jamie Spears of violating every known constitutional right known to man (hyperbole, but you get the point). He did all of this in spite of likely knowing that Britney was not in a good headspace as evidenced by the videos and other eye-raising stuff that she put out there in the world during the 4-month window between the filed petition to terminate and the official date of termination. Did he have a mental evaluation performed on her to be sure that what she wanted was not just achieving her goal, but in her best interest? Did he stop to think at any point that while a full conservatorship might be too much, a limited conservatorship (which does exist in California) might be a more appropriate vehicle so she could ease into a normal life? Or, in the alternative, how about ANY kind of arrangement short of a conservatorship that might give Britney a shot at a smoother transition? Maybe, this was attempted. Maybe, this wasn’t. We’d like to know.

Rosengart’s ‘blow it up’ strategy didn’t end with the end of the conservatorship. Instead of advising Britney to turn off her social media platforms and to disappear for a while so she could find herself again, he negotiated a book deal in spite of knowing all the while that she had serious mental issues to work through and that it might not be in her best interest. He also thought it would be great to draft the prenup when he knew it might not be in her best interest to get married. He could have demurred on both counts given his conservatorship work was done.

Which brings us to the motivation for this article. Last week, Rosengart released a statement to the Hollywood Reporter that his lawyer client relationship with Britney Spears had ended because he had worked with her to achieve her goals, that he had untangled her from all litigation (that had mostly been started by him) and so on. He ended it with a wink and a nod. “As I’ve always said, the credit goes to Britney.” It was also hinted in the Hollywood Reporter article that the intention all along was for Rosengart’s services to have an expiration date. Sure, there was. Just a snarky opinion.

To us, this statement can be perceived as meaning one or more things and none of them are good. The first interpretation is that it’s self-serving promotion. Rosengart is putting himself on the moral pedestal for a case that concluded years prior. That’s weird. The second interpretation is that Rosengart is intimating that Britney’s goals were all that mattered regardless of whether it was in her best interest. Not good. The third interpretation is that Britney was becoming a stage 5 clinger who took up too much of his time and he wanted to publicly end the relationship. If true, not good. The fourth interpretation is that Rosengart was planting a legal defense flag because someone connected to Britney might come after him on grounds we aren’t yet aware of…the old “Yes, I destroyed familial relationships and reputations, but that was Britney’s goal.” Maybe, this is a stretch, but who knows? The fifth interpretation is that he is absolving himself of accountability. “Don’t blame me if she or anyone else thinks her life took a turn for the worse. The credit goes to Britney.”

Bottom line:  Rosengart remained undefeated in the courtroom as of November 12th 2021, but it was also on that same day he lost his first case outside of it…and it is because of this that his ‘former client’ has to crawl her way out of a deeper hole…in our opinion.

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