Justin Bieber‘s and Scooter Braun’s success has been inextricably intertwined since 2008 when Braun discovered the then-13-year-old singer on YouTube, got him signed to Usher’s record label and became his manager. Braun made Bieber’s career, and vice versa, and their once-flourishing business relationship was arguably the catalyst for Braun adding Ariana Grande, Demi Lovato, J Balvin, Idina Menzel and many others to the management roster at his SB Projects, and the subsequent sale of its parent company Ithaca Holdings to Korean K-pop entertainment giant HYBE for $1.06 billion in April 2021 and his appointment as HYBE America’s CEO that followed.

But since then, Braun has moved his focus away from his management business and onto growing HYBE, shepherding massive deals like its $300 million purchase of hip-hop company Quality Control in February. That shift is one factor that’s had Bieber actively looking at how he might extract himself from that relationship with the help of his new music lawyer, David Lande, and prompting Braun’s other star clients to exit as well, sources tell Billboard. Grande is also planning to part with Braun on friendly terms, more because she’s “excited to go in a different direction” and because she’s “outgrown him” than because of his C-suite distractions, a source close to her says: “It’s time for something new.” Menzel, Balvin and Lovato departed earlier this year, on good terms as well, sources say.

But even for the world’s biggest superstars, leaving your manager is easier said than done — and Bieber and his lawyer are still exploring all their options, sources tell Billboard, with a full split not guaranteed. Bieber’s latest moves have included firing his agency, CAA, and hiring a new music lawyer — Lande at Ziffren Brittenham — to replace Aaron Rosenberg, whom Braun had helped hire. (Michael Rhodes, a partner at the Cooley law firm remains Bieber’s general counsel.)

Lande, these sources say, has been looking at how to extricate Bieber from the management agreement with Braun, but there’s a major complication: Bieber is still under contract for about four more years, following a series of amendments to their deal made three years ago, sources say, and standard management contracts tend to favor the manager. To get out entirely free of obligations, an artist must often show that their manager breached the agreement — which generally includes acting outside of an artist’s best interests, such as financial impropriety like siphoning funds. And only in the most extreme examples does a manager being unavailable or unreachable count. (Were that the case, Braun’s team at SB projects would likely give him significant cover: Braun’s lieutenant, Allison Kaye, has been running management as president of SB Projects since 2016.) Sometimes there are performance metrics, but given Bieber and Braun’s stature in the industry, that’s unlikely, music lawyers say.

“If you’re talking about a case where the artist is just no longer content with their current manager and wants to get out of their management deal, they have a high bar to clear,” says entertainment attorney Larry Katz. “The only chance an artist would have is if they can demonstrate a well-documented pattern of failure by the manager.”

That said, many managers and lawyers agree that it is not in anyone’s best interest to hold an artist in a contract against their will. “Slavery is not a thing,” says one manager.

A scenario like this usually results in the artist and manager striking a new deal that involves a lump sum paid to the manager; a commission on future monies made from deals in which the manager was involved; a sunset clause that gives the manager a gradually decreasing percentage of earnings from such deals — or, likely, a combination of these.

Perhaps because of these complications, sources familiar with some of Bieber’s business dealings say he is focused on resolving his predicament with Braun and would not begin a serious search for new management until that objective is completed — or may not seek a new manager at all.

Otherwise, Bieber would need to shoulder the cost of paying two managers until his agreement with Braun either expired or was dissolved.

A new manager would also face limited options for finding new income opportunities. Bieber is still under a recording contract with Def Jam as he currently works on his seventh studio album, meaning there’s no new multi-million-dollar label deal on the immediate horizon. He also sold his publishing, artist royalties from his master recordings and neighboring rights to Hipgnosis for over $200 million earlier this year. And he remains under contract with AEG Presents, which has promoted his concerts since his inaugural My World Tour in 2010.

Under that AEG deal, Bieber likely owes the promoter any advances paid for his tours that haven’t been recouped. This would likely include an upfront signing fee paid to AEG to promote Bieber’s tours, as well as a per-show guarantee — some or all of which would be recoupable against the tour’s ticket sales. These financial obligations are usually settled somewhere between the early planning of the tour and while it’s in progress, but Bieber’s situation is more complicated. That’s because he has repeatedly rescheduled or canceled touring plans over the past three years due to the coronavirus pandemic and personal health issues, which could mean that his deal with AEG has yet to recoup its obligations.

Still, sources agree Bieber remains an appealing client, because of the kind of influence that comes with his superstar stature.

As for the status of Bieber and Grande’s relationship with SB Projects, sources close to Braun’s camp say both artists are under contract but are currently working out new deal structures to account for Braun stepping into his larger role as HYBE America CEO. Sources close to Bieber and Grande say they are also working out new deal structures for the many business ventures they undertook while at SB — in preparation for their potential departures.

“It might take several years for Bieber to wrap up whatever deals he has with Braun and SB Projects, but he’s still a very attractive client,” says a major talent agent executive unassociated with the artist. “He’s young, he’s a proven superstar and he’s motivated to work and make money.”

Additional reporting by Dave Brooks and Elias Leight.