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Britney Spears’ longtime manager, Larry Rudolph, has officially resigned as rumors of the singer’s retirement continue to swirl amid her ongoing conservatorship battle

The resignation comes days after co-conservator Bessemer Trust also jumped ship from overseeing and assisting in the performer’s career and finances following a judge's denial of her request to remove her father, Jamie, from being a conservator and dissolving a legal arrangement they established in 2008.

In a letter addressed to Jamie Spears and the court-appointed conservator Jodi Montgomery Monday, Deadline reports that Rudolph officially tendered his resignation. Rudolph has been Britney’s manager for the majority of her career, including her rise to the top in the mid-1990s. 

"It has been over 2 1/2 years since Britney and I last communicated, at which time she informed me she wanted to take an indefinite work hiatus," Rudolph wrote. "Earlier today, I became aware that Britney had been voicing her intention to officially retire."

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The letter continues: "As you know, I have never been a part of the conservatorship nor its operations, so I am not privy to many of these details. I was originally hired at Britney’s request to help manage and assist her with her career. And as her manager, I believe it is in Britney’s best interest for me to resign from her team as my professional services are no longer needed."

Britney Spears' longtime manager, Larry Rudolph, resigned on Monday amid rumors she plans to retire from performing.

Britney Spears' longtime manager, Larry Rudolph, resigned on Monday amid rumors she plans to retire from performing. (Gabe Ginsberg/Getty Images)

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The Hollywood Reporter notes that Spears was first introduced to Rudolph when she was 13 years old in 1995. They worked together to secure her first record deal with Jive Records two years later and he would go on to act as her main manager and legal representative throughout the years. They parted ways in 2004, but reunited in 2007 at the behest of Spears’ father, Jamie. 

Although Rudolph was not named directly, Spears previously told the court that her father and those like Rudolph who have enabled her conservatorship over the years "should be in jail." 

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In her 24-minute address to the court in June, the star claimed that her father "loved" the control that he held over her thanks to the "abusive" guardianship. Spears asked for her statements to a Los Angeles courtroom could be shared publicly.

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"I am not happy, I can’t sleep. I’m so angry, it’s insane. And I’m depressed. My dad and anyone involved in this conservatorship, including my management… they should be in jail," Spears said at the time.

Fox News' Nate Day and Michael Ruiz contributed to this report.