Despite the extensive coverage, Jeffrey Epstein remains an enigmatic figure. While we know a lot about him, there are still many unanswered questions.

The recent release of Department of Justice documents has unveiled more about Epstein’s connections to influential figures across politics, business, academia, media, entertainment, and high society. The revelations have had significant repercussions, leading to the downfall of several high-profile individuals due to their associations with the convicted sex offender.

Beyond the headlines, these documents also provide an intimate look at Epstein’s personal preferences and peculiarities. They reveal details about his tastes, habits, temper, and health issues, as well as his casual conversations with his brother.

Here are six intriguing insights into the life of the disgraced financier, offering a perspective only possible through a deep dive into the Epstein files, which we’ve been examining closely over the past two weeks.

From hot water bottles to ‘I Can’t Believe It’s Not Butter’

Epstein was remarkably meticulous about his residences, obsessing over even the tiniest details related to landscaping, furniture, and linens in his homes located in New York, Palm Beach, the Virgin Islands, New Mexico, and Paris.

His correspondence, including emails and messages with co-conspirator Ghislaine Maxwell, longtime girlfriend Karyna Shuliak, and various employees, alongside a manual for his staff, provides a detailed account of how he expected his households to be managed.

Those include staffers tucking hot water bottles under his covers precisely at 7pm every evening, and each morning preparing a French press containing exactly eight scoops of ground coffee and special ‘JE muffins’ – filled with bran (recipe here) to keep him regular. 

The muffins were to be heated in a microwave for 25 seconds and served with a spray bottle of I Can’t Believe It’s Not Butter.

Refrigerators in Epstein’s master bedrooms needed to be stocked daily. Household staff had to call him ‘sir’.

And, beside each phone in each of his homes, ‘there must always be a selection of reading glasses (prescription of 3.5) with a large and small note pad, 3 pens and 3 pencils. Glasses should be checked daily for cleanliness,’ the staff manual reads.

Emails show that Epstein sent Shuliak – his girlfriend for nine years before his death – for special training in Japan and to a finishing school in Switzerland to learn to run his households and their employees according to his exacting specifications. 

That was after he bought her acceptance in and paid her way through Columbia University’s dental school.

Shuliak studied ‘etiquette and protocol’ at Institut Vito Pieirefeu, the finishing school near Geneva, writing on her application that she hoped to gain ‘the ability to hold salons in New York.’

It was to her that Epstein bequeathed most of his real estate holdings and wealth two days before his 2019 suicide in a Manhattan jail cell. Now 36, she has yet to cash in because victims’ legal claims against his estate are still pending.

Beef jerky

Epstein may have appreciated the finer things in life, but he also took beef jerky seriously. So seriously, in fact, that the word jerky appears 380 times in the Department of Justice files.

The financier was especially partial to jerky made by Francis Derby, owner of the now-shuttered Cannibal restaurant in New York, who was on Epstein’s payroll.

At one point in 2012, the chef wrote, ‘We have gone through about 70 pounds of Steak for beef jerky in the last 2 weeks.’

Epstein put the jerk in jerky in an email to Derby two months later, slamming him for not keeping up with his demand.

‘I am concerned that after being off and then being back since monday, that somehow i have no jerky again. I am very very annoyed,’ he wrote.

Derby, as it turns out, was in the hospital at the time.

Another email shows Epstein taking Derby to task for not having had the nutritional value of the jerky analyzed and tested as he had requested: ‘We talked about this at the ranch, why isn’t it done,’ he wrote.

Yet another badly spelled email shows the financier excoriating Derby about the appearance of crunchy ‘prosciutto bits’ the chef had prepared for him, writing, ‘I would Ike an explaintion of how you find this presentaion acceptable [sic].’

After Derby taught Epstein’s staff how to make jerky themselves using his special recipe, dozens of other emails show assistants keeping a constant track of their supply and arranging for it to be flown and FedExed to him all around the world. 

One staffer can be seen promising to ‘make jerky happen,’ while another suggests that colleagues ‘liaise’ about jerky.

Online dating

Epstein took a multi-pronged approach to finding new sexual targets.

In addition to procuring girls and young women through escort services, modeling agencies and networks of people scouting for him in New York, Florida, eastern and western Europe, the Middle East and elsewhere, he sometimes picked them up on the street.

But his trolling didn’t stop there.

Emails show that the world’s most notorious sexual predator was also on at least four online dating sites.

Those include Match, where he called himself ‘Sultan 175’ in his 2012 quest for what the site called a ‘special someone.’

He was also on OKCupid, where he went by ‘gggeb,’ briefly in 2011, as well as Jdate – a Jewish dating site – posing as ‘Edward242E’ in 2013, and was also on EHarmony in 2009.

Justice Department documents show some of those sites sent him daily suggestions for women in their early 20s, although it is unclear whether the financier ever used the apps to reach out to them.

Epstein was required to register as a sex offender after his 2008 conviction for soliciting sex from a minor.

Most dating apps do not automatically check if people have criminal histories or are registered on sex offender registries when they sign up. They instead rely on users agreeing that they aren’t offenders but fail to verify that information independently.

Against the odds

Epstein started his career as a high school math teacher and later went on to fund research by some of the world’s foremost mathematicians.

Although he must have known the improbability of winning the lottery, he nevertheless played it – both for himself and others.

In 2015, with the Powerball jackpot at $485 million, he bought 100 tickets to hand out among people he and his staff referred to as the ‘girls.’

Emails show that in 2016, he bought $100 in Powerball tickets for his friend, Woody Allen, and had them sent via messenger to the director’s home.

That same month, he bought another $100 worth of tickets for Erika Kellerhals, a tax lawyer in the Virgin Islands. And when the Powerball jackpot grew to $900 million, he bought tickets for every employee working on the islands he owned off St Thomas.

When informed that her boss had bought her $24 in Powerball tickets, his longtime scheduler, Lesley Groff, thanked him and wrote, ‘Even if I win I will still be your assistant! :)’

One tip passed to then-FBI director Robert Mueller in 2009 claimed that the Epstein-owned Zorro Trust won an $80 million lottery ticket in New Mexico. 

Several worldwide news outlets have reported that the payout went to Brice Gordon, who managed Epstein’s Zorro Ranch in Santa Fe for several years.

The Daily Mail has found no evidence confirming Gordon’s win, and New Mexico’s lottery system has not responded to our inquiries. Gordon could not be reached for comment.

A human Petri dish

Epstein had a host of ailments.

The sex offender tested positive for chlamydia in 2015, and for gonorrhea in 2016 and 2018.

He also had low testosterone levels for at least the last 15 years of his life, testing ‘extremely low’ in the months before his 2019 death.

Such low levels can cause decreased energy and libido in men. The pedophile, who for years reportedly engaged with multiple sex partners daily, had been discussing testosterone replacement treatment as an option.

A letter from the head neurologist at New York Presbyterian/Weill Cornell Medical Center shows he had reached out for help related to his sexual health in the last year of his life.

Emails, text messages and medical records in the DoJ files also show Epstein had persistently high triglycerides and cholesterol levels, plus a host of other medical woes at one time or another. 

They included chronic sinus problems, sleep apnea, ‘terrible sciatica,’ Lyme disease, whipworm and entamoeba histolytica (both parasites), angioedema – deep-tissue swelling in his face, lips, eyes, hands and feet – bladder polyps, ‘bright red blood‘ in his stool, rashes, feather allergies and constipation (see bran muffins above).

By the time he was booked at a federal prison in Manhattan in July 2019, he was on ten active prescriptions and using a CPAP machine to sleep.

Epstein kept his Florida-based general practice physician, Bruce Moskowitz, on speed dial, emailing and texting him at all hours of the night and taking a near-hypochondriacal interest in even the smallest details of his health. He donated at least $150,000 to Moskowitz’s family foundation in return for his patience and ‘friendship’. 

Emails also show Epstein had been cryogenically freezing his sperm.

‘Puggy’

Epstein’s only sibling and surviving family member, Mark Epstein, is a real estate investor and property developer in New York whom friends and family reportedly call ‘Puggy.’

In Epstein’s psychological evaluation before his death, he said he and his brother weren’t particularly close.

Some of their emails show them occasionally checking in with each other and their travel plans. Others – especially those about their late parents, Pauline and Seymour – reveal their brand of Coney Island irreverence.

‘Was Seymour really part ape?,’ Mark asked his brother in one email.

In another string from 2012, he wrote, ‘When we were kids and Seymour used to take a bath, he used to call Paula in to ‘wash my back.’ Do you think he wanted his back washed?’

‘Aghhhhhjh,’ Jeffrey wrote back.

‘Funny huh? Where are you?’ Mark wrote.

‘Paris with woody allen,’ Jeffrey replied.

‘For les pedophile convention?’ Mark quipped.

‘i think pedophilee is the plural,’ Jeffrey responded.

Mark seemed comfortable with his brother’s sexual plundering.

‘Do you remember the name of the Gynocologist that you used to send your victims to?’ he asked his brother months later.

‘Ny?’ Jeffrey wrote, as if there were also others in different cities.

‘Yes, many years ago you used to send them to a gyno in NY who once commented something to the effect that you were keeping him in business singlehandedly.’