What to expect at Britney Spears's Sept. 29 conservatorship hearing: Jamie's fate to be decided

With the cries to #FreeBritney at a deafening pitch, Britney Spears will have yet another day in court — and a pivotal one as she works to break free from the conservatorship she's been in since 2008.

The next conservatorship hearing is Wednesday, Sept. 29 at 1:30 p.m. PT/4:30 p.m. ET. It will take place at the Stanley Mosk Courthouse in L.A., though the superstar will likely appear virtually as she has previously.

There are several items on the docket, but at the top is the removal of the star's father, Jamie Spears, as conservator of her estate. And, if that box gets checked, there will also be the appointment of a temporary conservator to replace him. Britney's attorney Mathew Rosengart wants the replacement to be certified public accountant John Zabel. Jamie has no plans to step down and, in a filing Monday, tried to discredit his potential replacement.

Going into the hearing, it is not expected that the conservatorship will end on Wednesday, despite Jamie petitioning for it. Rosengart has made it clear his primary goal is removing Jamie, who Britney has accused of conservator abuse. The conservatorship ending would be his second priority, though he's already said his target date for it to end is this fall.

"I don't believe the conservatorship will terminate on Sept. 29," California-based family law attorney Christopher C. Melcher of Walzer Melcher tells Yahoo Entertainment. "Britney's lawyer is saying she's in favor of terminating the conservatorship, but there are loose ends that need to be dealt with. Rosengart wants it to wind down rather than just end abruptly."

Jamie's call to terminate the conservatorship, in docs filed on Sept. 7, has really been "a strategic game," says Melcher, who thinks "Jamie's trying to walk out of this scot-free."

While it makes a good headline that Jamie was the one calling for the conservatorship to be terminated, his filings spell out very specific prerequisites to him doing so. One, is having the accounting being approved — so that he's not on the hook for over $1 million.

We've looked at the specifics before, but Jamie wants Judge Brenda Penny to sign off on expenditures he made as conservator — notably charges Britney is disputing. It includes $1.3 million in attorney fees Jamie rang up fighting his removal, including $531,065 spent on "media matters" for a crisis PR expert. Also at issue is a $500,000 payment to Britney's former business manager, Tri Star Sports & Entertainment Group. The company, under Lou Taylor, had been getting a five percent commission on Britney's gross entertainment-related income. However, when Britney went on a work strike — unhappy with her father and management — the company was suddenly only receiving $200,000 annually. Tri Star asked for a minimum of $500,000, despite the agreement in place, and Jamie OKed it.

Another reason Jamie made this 180 to terminate the conservatorship, instead of stepping down, is to protect himself.

"Most importantly, Jamie wants the conservatorship to terminate so that all of the communications that he's had with the attorneys for the conservatorship would remain privileged," Melcher suggests.

He explains, "Basically everything Jamie has done since the conservatorship was put in place in 2008 was done in a representative capacity. That includes hiring the lawyers — and communicating with lawyers. In a normal attorney-client relationship, it's the individual client talking to the lawyer and all of the communications are privileged forever. But here, Jamie is acting on behalf of the conservatorship when he hired these lawyers and acting on behalf of the conservatorship when he spoke to them. Therefore, if he is replaced and a new person is installed as a temporary conservator, that person then holds this privilege and would have the right to demand — and would get — all of the files for the last 13 years between Jamie and the attorneys that Jamie probably thought would never see the light of day. And those attorneys probably thought would always be kept secret but now could be revealed."

So if Rosengart gets his way — pushing out Jamie and putting in temporary conservator Zabel — the replacement "substitutes in as the client, representing the conservatorship, and is then entitled to receive all of the communication that Jamie has had with Holland & Knight and Freeman, Freeman & Smiley — two law firms he's been involved in communicating with for 13 years."

Melcher says it's "potentially a gold mine of evidence." The findings could be "explosive" and would likely include communications about Britney's complaints about the conservatorship and how she's wanted it to end. There would likely be communications in there about the surveillance on Britney. The latest New York Times documentary about the conservatorship claimed that Britney's communication was secretly monitored and audio recordings were captured in her bedroom, including conversations with her boyfriend and two sons.

"It would be damning evidence for everybody involved," Melcher predicts.

Now if the judge doesn't remove Jamie tomorrow — or before the conservatorship terminates — that privileged communication could still be obtained by Britney's new legal team, who have said they want Jamie held accountable. However, "It would just be harder to get," Melcher says.

That is all bigger picture, however. In the immediate future, this hearing, the only thing "that is truly in play" is the request to remove Jamie and put in this replacement," Melcher says. "Ending the conservatorship isn't really a power that the court would have on Wednesday. Also, there are the financial issues that are supposed to be resolved — about the media matters — but those will be tabled, I imagine, and dealt with as the conservatorship is wound down."

As for whether Jamie will stay or go, at this point, Judge Penny has been told by Britney herself that she wants Jamie out. She's been informed by Rosengart of the surveillance allegations, and Jamie's spending has been called into question. Plus, Jodi Montgomery, the conservator of Britney's person, has said Jamie being removed is what is best for the star's mental health. So there's a lot in favor of ousting him on Wednesday.

And that is what Melcher thinks will happen, saying, "The judge would just be failing to protect Britney by not doing so."