Why was Jeffrey Epstein allowed to purchase small women’s panties from the Palm Beach jail?

A decade ago, during a brief stint in Palm Beach County Jail, convicted sex offender Jeffrey Epstein made an odd purchase at the facility’s store: two pairs of small women’s panties, size 5.

It was just one of thousands of dollars of purchases made by the disgraced financier while in jail after pleading guilty in 2008 to soliciting a minor for sex, according to a purchase log. (His top purchase was single-serve cups of coffee, of which he bought more than 800 in 13 months.) But the panties raise questions about why a childless male inmate, accused of sexually abusing girls as young as 14, would be allowed to buy female undergarments so small that they wouldn’t fit an average-sized adult woman.

The panties were certainly too small for Epstein, who also purchased his briefs in men’s medium and sweatshirts ranging from XL to 3XL, and size-12 shoes. So what, or who, were they for, and why wouldn’t the purchase raise eyebrows under the circumstances? It’s one of many questions that arise from thousands of pages of records obtained by the Miami Herald from the Palm Beach County Sheriff’s Office.

The stockade held male and female inmates, separately, explaining why the panties would be stocked.

On Friday, the Palm Beach Sheriff’s Office, which runs the jail and stockade, handed out the records of his stay, during which he was allowed to leave the stockade in a chauffeur-driven car and deposited at a downtown West Palm Beach office building for a 12-hour-a-day, six-day-a-week respite from incarceration.

The records came out too late Friday to get a comment from Sheriff Ric Bradshaw or his spokeswoman. Bradshaw has faced increasingly fierce criticism — and his department is now under investigation by the Florida Department of Law Enforcement — for its seemingly soft treatment of the multimillionaire hedge fund manager, who was, according to the records, allowed to wander in and out of his unlocked cell at will.

That investigation is separate from the Justice Department probe looking at why then-federal prosecutor Alexander Acosta decided to shelve a 53-page sex trafficking indictment against Epstein, which could have put him away for life.

Listen to today's top stories from the Miami Herald:

And now there is yet another pending investigation, this one looking at how Epstein, rearrested at 66 in early July on renewed sex trafficking charges, was able to hang himself last Saturday in a New York City jail cell while awaiting trial. The new charges were filed after the Miami Herald published a series on Epstein’s 10-year-old case, Perversion of Justice, that examined, among other things, Acosta’s decision to give in to a defense demand that victims not be told about the earlier federal charges being dropped.

The Manhattan cell where he took his own life — in a hardscrabble lockup notorious for bugs, rodents and rough jailmates — was a stark contrast to his surroundings in Palm Beach County in 2008.

What’s clear from the Palm Beach sheriff’s records is that Epstein’s wealth provided him extraordinary privileges during his 13-month stay in Palm Beach stockade from June 30, 2008 to July 22, 2009 — an unlocked cell door, almost unlimited access to a TV, and a perhaps uniquely generous work release program that meant he spent almost as much time outside the jail as in it.

The longer he stayed, the cushier things got. Six-day-a-week work release was extended to seven. Hours outside the cell were extended from 12 to 16. He was permitted to pass some of the time at home. Records that once referred to him as an inmate now called him “client.”

Deputies, required to wear business suits, provided “security” for Epstein while he was on work release. They guarded the door to his office or home, sometimes from the outside, rather than keeping an eye directly on Epstein, while the inmate was on structured leave from the jail. Some deputies expressed relief in their daily reports that he seemed pleased with services rendered.

The records from Palm Beach suggest the local sheriff’s office never intended to treat the convicted sex offender as a typical inmate — explicitly because of his extraordinary wealth.

In an email on the day Epstein reported to jail, Capt. Mark Chamberlain wrote that the new inmate was a person of “unusual means” and expressed concerns that other prisoners might try to extort or manipulate him.

“His financial status lends itself to his being victimized while in custody and as such, he has been placed in special management,” Chamberlain wrote. “He is poorly versed in jail routine and society and his adjustment to incarceration will most likely be atypical. For the time being, I am authorizing that his cell door be left unlocked and he be given liberal access to the attorney room where a TV will be installed.”

All this while serving time for soliciting sex with a minor — a charge Epstein agreed to plead guilty to only after Acosta, then the U.S. attorney for Southern Florida, killed an already drafted sex-trafficking indictment that could have put him away for life.

During his stint in Palm Beach County custody, Epstein was required to be physically present in the jail for about 60 percent of the time during the 13 months he served, far less time than originally reported by PBSO when questioned by the Miami Herald and other media outlets. According to calculations based on internal emails describing his work release, Epstein was approved to spend over 40 percent of the time at his office, at home, or at a variety of doctor appointments.

Bradley Edwards, an attorney for some of the women who accuse Epstein of having recruiters lure girls to his Palm Beach estate for massages that turned into sexual assaults, has alleged that Epstein used his work release hours to engage in sexual exploits behind closed doors. A release of court records earlier this month quoted a young female college student allegedly recruited by Epstein’s associates saying he required “three orgasms a day” to function. “It was biological. Like eating,” she said Epstein told her.

The record of who visited Epstein while on work release — a daily log maintained by deputies and tucked away in a safe — has been destroyed. Explaining that decision, the sheriff’s office cited legally prescribed retention schedules that allowed for the book’s destruction. But many records from that time remain for investigators to examine, including the thousands of pages of just-released records.

The records provided Friday list every deputy assigned as plainclothes “security” for Epstein during his work release. The deputies, paid for by Epstein, are potential witnesses in what is an ongoing Florida FDLE investigation of Epstein’s treatment by PBSO and its longtime sheriff, Bradshaw.

Purchase records from the jail’s commissary are a reflection of the hedge fund manager’s eclectic personal habits, which included an insatiable sweet-tooth, and a focus on physical appearance and personal hygiene. The prisoner’s purchases, $2,000 worth in all, included hundreds of snacks, from large Hershey’s almond bars to Sour Cheddar Ruffles, hair gel, seven bottles of shampoo, and 22 tubes of toothpaste.

Early during his jail stretch, one of Epstein’s paralegals was caught bringing Epstein a book titled “Face Exercises that Prevent Premature Aging.” Someone also smuggled in more hygiene products, including three additional tubes of toothpaste — brands that weren’t available on the jail shelves. All of that was confiscated as contraband, records show.

After three and a half months in the stockade, Epstein was granted work release by the sheriff’s office, allowing him 12 hours a day, six days a week at his private office, as well as permitting regular trips to a chiropractor. While on work release, Epstein was supervised by off-duty deputies who were required to wear business suits, not uniforms. They were paid hourly by Epstein, according to work release records. Epstein also paid $84 per week to PBSO as a standard work release fee.

The arrangement came to the attention of Assistant U.S. Attorney A. Marie Villafaña, who wasn’t pleased. On July 3, 2008, she wrote a letter to PBSO Deputy Chief Mike Gauger that letting Epstein spend time in a private office “making telephone calls, web-surfing, and having food delivered to him is probably not in accordance with the objectives of imprisonment.”

Villafaña noted that the situation seemed to violate PBSO’s own policies and asserted that the financier had misrepresented details about the made-to-order charity where he purportedly worked while on work release.

Work release programs are meant to help inmates maintain their lives outside jail walls and reintegrate into society. But Epstein’s was loaded with perks.

The first version of Epstein’s work release agreement showed he was not to leave his workplace for any reason, “with the exception of returning to the PBSO stockade, or for emergency medical treatment.” Epstein, the document added, “cannot leave for lunch.”

But a revised version filed 13 days after he began his work release changed that language to read simply that Epstein could leave his place of employment “only if authorized by [PBSO’s] Alternative Custody Unit.”

The alteration allowed Epstein to make at least 69 doctors’ visits in six months, records show. Many of the trips were to a chiropractor in Lake Worth. Epstein would go as many as three times a week. Sometimes he would have more than two medical appointments the same day. He had so many appointments that off-duty deputies monitoring him had a hard time keeping them straight, the records show.

The second draft of the work release agreement also changed how it referred to one of the stockade’s most notorious inmates — from “inmate Epstein” in the first draft to “Jeffrey Epstein” in the rewrite.

Why top officials at the law enforcement agency granted Epstein’s generous work release request isn’t clear. The decision was PBSO’s alone, the agency has said. The Herald has attempted to interview Bradshaw for a year to no avail.

The work release agreement was negotiated with Epstein’s team of high-priced attorneys, led by Darren Indyke, who wrote the initial request on Epstein’s behalf and is also listed as the vice president of the foundation where Epstein worked during his release.

“His legal staff that he had was enormous,” Deputy Chief Gauger acknowledged during a video interview the sheriff’s department posted online.

In an Oct. 23, 2008, internal email discussing the changes to Epstein’s work release agreement, Lt. Steven Thibodeau wrote: “I realize that this permit is very unique; however, job profiles are often modified to satisfy the clients’ needs or provide clarification. Considering the sensitivity of this permit, I would ask that you consider the proposed revised job profile.”

Maj. Michael Veccia signed off, writing “have one of the Corrections Majors approve the changes.”

Epstein paid the sheriff’s office more than $128,000 to cover the cost of deputies’ supervising him off duty. Their rates began at $42 per hour, documents show.

In a subsequent email from Villafaña, she told PBSO that the agency’s own policies on work release barred felons, like Epstein, who had committed at least three offenses under Florida’s anti-prostitution statue from going on work release.

While Epstein’s attorneys argued that his conviction on a single count exempted him from the prohibition, Villafaña noted, “in order to be convicted of a felony violation of that statute, one must commit ‘a third or subsequent violation.’ In other words, Mr. Epstein has committed at least three violations” and is therefore ineligible for work release.

Villafaña also informed the sheriff’s office that elements of Epstein’s work release application seemed to be a sham. For instance, she wrote, Epstein had rarely worked for the West Palm Beach charity where he planned to spend his days while incarcerated, as he claimed in his application.

In fact, the Florida Science Foundation was registered to operate in Florida not long before Epstein went to jail in 2008. And its officers, including Epstein’s “supervisor,” were paid attorneys working for Epstein, Villafaña said.

“The foundation, its offices, and Mr. Epstein’s purported job schedule were all created on the eve of Mr. Epstein’s incarceration in order to provide him with a basis for seeking work release,” Villafaña wrote.

It’s not clear how the sheriff’s office responded to her concerns. (Villafaña, who herself signed off on the controversial non-prosecution agreement with Epstein that allowed him to escape a federal indictment in order to plead to lesser charges in state court, recently resigned her position with the U.S. attorney’s office.)

The Florida Science Foundation was dissolved the year Epstein was released, state records show.

Miami Herald inveestigative reporter Julie K. Brown researcher Monika Leal contributed to this report.