"I represented and still do represent Mr Federline, her [Britney's] former husband," Kaplan formally introduced himself on the show.
"What are your thoughts on what she's going through at the moment and that her father essentially has control of her finances and her assets?" asked host Erin Molan.
"Well the conservatorship that has been in place now for an excess of 10 years came into place shortly after Britney had that very famous and publicly viewed meltdown," he explained.
"It was in context of the divorce case and custody case that was ongoing, and I can tell you because it is public record, that her finances were in quite a state of turmoil at that time.
"I also know that since the conservatorship has been in place for almost 12 or 13 years – even though it's called a 'temporary conservatorship' – for what I hear reported is that the state is worth north of $60 million, so in that regard I think it serves her well."
"It doesn't deserve the flack it's getting," asked Dave Hughes.
"Well whether or not she is capable of managing her own finances I don't know," Kaplan continued.
"As far as the #FreeBritney movement goes, saying that she is somehow being held against her will and is trying to get out secret, dyslexic based messages on a scrabble board – it's hard for me to imagine.
"She is living in Los Angeles … it's not this fascist gulag. It's not like if you wanted to get a message out you'd have to write it in code on the back of a piece of birch bark and throw it over the side of the fence."
"She's not locked in a basement is she," asked Hughesy.
"You make a good point," added Erin Molan.
She continued: "Kevin Federline who you still represent has children with Britney … and I don't care how nasty a divorce is you're always going to care about the mother of your children. Does he still have contact with Britney? What's that relationship like at the moment? Does he have faith that Britney is okay?"
"Well they have shared custody of two young teenage boys, and while Kevin has the primary allocation of time with the kids he has never tried to unreasonably interfere with Britney seeing the boys or the boys seeing Britney.
"Kevin's relationship with Britney is a good relationship at this time and the conservatorship, probably provides some degree of security that things are in organised and structured environment when the boys have allocated time with Britney. If it wasn't there we'd have to re-evaluate."
"Britney is still paying child support?" asked Hughesy.
"Yes Britney pays child support to Kevin," Kaplan revealed.
This eye-opening chat comes shortly after Britney's father's lawyer claimed that Jamie Spears saved his daughter's life.
The 68-year-old has been the subject of growing scrutiny, particularly in the aftermath of the controversial documentary.
The doco explores the rise of Britney's fame, her mental health struggles, being under her father's conservatorship and the subsequent mobilisation of the #FreeBritney movement set in motion by her fans.
While it's widely believed Jamie has controlled her life and fortune, his lawyer Vivian Thoreen has told ABC News that The New York Times' documentary "has it all wrong".
"I understand that every story needs a villain but people have it so wrong here," Ms Thoreen said, adding Jamie was a "furiously loving, dedicated and loyal father who rescued his daughter from a life-threatening situation".
"People were harming and they were exploiting her," she said.
While Ms Thoreen didn't detail the "life-threatening situation" she said, "Jamie saved Britney's life. Britney's assets were clearly being mismanaged and she was being taken advantage of financially by some of those around her."
Spears' boyfriend Sam Asghari, who has been dating the singer since 2016, recently called out Jamie for allegedly "trying to control" his relationship with her.
"It's important for people to understand that I have zero respect for someone trying to control our relationship and constantly throwing obstacles our way," the 27-year-old said on his Instagram Story after the doco aired. "In my opinion, Jamie (Spears) is a total d**k."
In November, Britney's lawyer, Samuel D. Ingham III, claimed in a hearing that the Toxic singer had become "afraid" of her dad and wanted him removed from her conservatorship.
The case returned to court in early February, where a judge overruled Jamie's objections to an order that established Bessemer Trust Co. as co-conservator of her estate.
