Many artists find that the fame that comes with their music becoming popular also means less privacy in their personal lives, and Britney Spears is a prime example. Living in the spotlight means that not only has the public always watched Britney’s every move, but they are also privy to her relationship drama. With three marriages (and divorces) under her belt, Britney Spears may have more fans worried about her than ever before.

This isn’t anything new, however, because it seems Britney’s previous relationships have all had an element of intrigue. With one specific ex, he was not only an employee of hers, but also became her co-conservator for a time, before the relationship imploded. Years later, Britney’s ex Jason Trawick maintains that she “needed” the conservatorship, and didn’t mince words regarding his perception of Britney’s struggles.

Britney Spears’ Relationships Have Always Been Of Interest To Fans

Ever since she dated fellow pop star Justin Timberlake, Britney Spears’ romances have been a source of interest to fans and the media. While it was once assumed that Britney and Justin were end-game, he was only one of the many people Britney would go on to date throughout her career.

Although Justin was later accused of treating Britney poorly, it can’t be said that her other exes did any better. Britney’s ex-husband Kevin Federline was always assumed to be leaching off his then-wife; the two divorced right after their second son was born, and Kevin later got full custody of the kids.

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Britney’s first husband, to whom she was married for a matter of days, crashed her wedding to Sam Asghari, revealing his own issues, but Britney’s third marriage unfortunately didn’t last either.

Yet looking back, Britney Spears’ list of exes also includes one person who flew under the radar at the time, even though he reportedly had a heavy hand in managing Britney’s career and life at that time.

Britney Spears Once Got Engaged To Jason Trawick

Back in 2010, Britney Spears turned heads yet again when it was revealed that she was dating her then-agent. Jason Trawick worked for Britney up until they went public; he reportedly resigned in order to separate professional from personal.

Of course, the two were said to have begun dating in 2009, so it’s possible that for a time, their professional relationship intermingled with the personal one.

Then, when the two got engaged in 2011, things shifted. By 2012, Trawick was given the role of co-conservator with Britney’s dad, Jamie Spears. At the time, publications suggested that the engagement may have been a way out of the conservatorship for Britney.

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When they got engaged, Britney had been under conservatorship for five years already. It’s worth noting that Jason was hired in 2006 to manage Britney’s career, two years before the conservatorship started.

It might be hard to argue that Jason Trawick had any say in how the conservatorship came about, or the fact that Britney was placed under one, but some of his comments seemed troubling in the aftermath of Britney’s testimony about the conservatorship.

Jason Trawick Said Britney “Needed” The Conservatorship

While many people may have seen Britney and Jason’s engagement as a way for the pop star to break free from her dad’s control, Jason himself didn’t see it that way. According to a quote from Trawick, Britney was better off in the conservatorship.

Jason was quoted as saying, “Listen, did she need a conservatorship when I was there? Yes. I’ll be the first to say it. I think she needed some guidance.”

Other reasons Jason maintained that Britney needed to be under conservatorship? She wasn’t good with money, not understanding how much things cost, and needed “therapy [and] stopping her from seeing certain individuals that were not great [influences].”

Because the court proceedings largely centered on Jamie Spears, the dissolution of the conservatorship didn’t seem to touch on Jason Trawick’s past involvement. Later, Jason would defend himself by suggesting that Jamie didn’t like him much, and even fired him once he began dating Britney.

Jamie Spears allegedly told Jason he couldn’t be both Britney’s agent and her boyfriend, so Jason “got fired.” As for the conservatorship piece, Jason also claimed that Britney asked him to become a co-conservator, something her dad permitted.

Given that it was so long ago, Britney has likely moved on, but looking back, that era of her life was a difficult one. Fans already know what Britney went through as her dad forced her under conservatorship, and even Sharon Osbourne had insider stories from her time working with Britney on The X-Factor.

Sharon pointed out that during The X-Factor, Britney was being fed lines through an earpiece by none other than her agent/boyfriend Jason Trawick. To hear Sharon tell it, that wasn’t a positive thing, as Britney’s every word was controlled by someone else.