He became famous as the celebrity lawyer of a porn star who sued Donald Trump and even touted himself for president, but today Michael Avenatti sits in a notorious New York jail.
The 48-year-old was brought Friday to the city's Metropolitan Correction Center (MCC), a high-security prison that housed Mexican drug lord "El Chapo" and wealthy sex offender Jeffrey Epstein.
Avenatti is awaiting trial on charges he allegedly tried to extort millions of dollars from the sports apparel giant Nike and embezzled funds from adult film star Stormy Daniels.
His attorneys say he is being held in solitary confinement in a freezing cell once occupied by Joaquin "El Chapo" Guzman on a floor that houses detainees charged with terror offenses.
"The temperature in his cell feels like it is in the mid-40s (Fahrenheit)," they wrote in a letter to the judge Monday.
"He is forced to sleep with three blankets. Not surprisingly, he has been having great difficulty functioning," the lawyers added.
Avenatti's situation is a far cry from the dizzy heights of February 2018 to March 2019 when he was the lawyer for Daniels, whose real name is Stephanie Clifford.
He became a household name during her legal battles with Trump over hush money she received for an alleged affair with the president in 2006.
- R. Kelly -
Avenatti's stock could not have been higher as he reveled in his role as outspoken critic of Trump and darling of America's left.
The brash California-based attorney, a keen racing car driver, was rarely off television news shows and built up a massive Twitter following.
He was a high-profile thorn in the side of Trump ex-lawyer Michael Cohen who was later jailed for fraud.
Avenatti also represented Julie Swetnick, who said she witnessed sexually abusive behavior by Brett Kavanaugh, during Kavanaugh's contentious nomination to the US Supreme Court.
In February 2019, Avenatti said his office had previously unreleased footage of R&B superstar R. Kelly having sex with a young girl.
He even toyed with the idea of running for the 2020 Democratic nomination, portraying himself as an aggressive street fighter.
Too many Democratic candidates, Avenatti said, "have a tendency to bring nail clippers to a gunfight."
But he abandoned the idea in December 2018 as his star started to wane.
In November 2018, Avenatti was arrested on a domestic violence charge, which was later dropped.
The following March, Clifford sacked him as her lawyer.
Their relationship had earlier soured after Avenatti filed a contentious defamation suit against Trump that Clifford lost and which she said had been lodged without her approval.
- Legal troubles -
Avenatti's legal problems also began in March 2019, when he was accused of attempting to extort more than $20 million from Nike and for embezzling a client's money.
He was arrested in New York based on separate complaints filed in that city as well as in California.
Prosecutors say Avenatti accused Nike of being involved in a basketball bribery scandal and threatened to go public with his allegations unless it agreed to multi-million dollar payments to him under the guise of legal work.
In April 2019, Los Angeles prosecutors indicted him on 36 charges of theft, fraud and tax evasion, theoretically exposing him to over 300 years behind bars if convicted.
Then in May, Manhattan prosecutors charged Avenatti with falsifying documents to pay himself about $300,000 intended for Clifford as part of an advance payment for her memoir.
Avenatti -- who has continued to tweet regularly, often about the Democratic race or Trump's impeachment -- was arrested by LA police last week and remanded over bail violations.
He was transferred to New York pending his trial, due to start April 21.
His lawyers have asked he be held in a regular unit and be allowed to use a computer and keep documents in his cell.
"If I'm ever going down (and I'm not), I'm going down swinging. It is all I know and it is how I am built," Avenatti tweeted earlier this month.