A Tale of Two Jeffreys: How the Virgin Islands Welcomed a Rich Sex Offender—and Punished a Poor One

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From the Virgin Islands comes a tale of two Jeffreys, and the difference great wealth can make when it comes to sex crimes—until it doesn't.

Both Jeffreys were convicted of shameful crimes that required them to register as sex offenders in whatever state or jurisdiction they resided.

Jeffrey Epstein pleaded guilty in Florida to engaging a minor in prostitution in a 2007 plea deal only a super-rich guy could have swung. He did 18 months locked up, mostly in a private wing of the Palm Beach County jail, where he only stayed at night, returning each morning to “work release.”

He then proceeded to prove that a registered sex offender with enough money in the Virgin Islands can just continue to come and go from a private island off the coast of St. Thomas, with an ever-changing entourage of girls who appeared to be barely in their teens. He would announce his periodic return by raising the American flag over the opulent hideaway identified on the maps as Little Saint James Island, but known to locals as “pedophile island.”

Jeffrey No. 2—Jeffery Cole—was convicted in Ohio of a misdemeanor charge of voyeurism in 2009. He was a schlub of modest means, but his offense was relatively minor (if creepy) and he needed neither wealth nor influence to receive just a suspended sentence of 90 days and two years probation.

“The underlying conviction, which requires Mr. Cole to register as a sex offender, did not involve a minor, physical violence, or physical touching of any kind,” his present attorney, Melanie Turnbull, noted in court.

We Found Red Flags All Over Jeffrey Epstein’s Jail Records

Once he successfully completed probation, Cole moved to Georgia, where he registered as a sex offender. He moved to the Virgin Islands in 2018 and has not been charged with engaging in further voyeurism or any other crimes.

The problem for this Jeffrey was that he failed to register promptly in his new home as a sex offender. The U.S. Attorney for the Virgin Islands, Gretchen Shappert, did not miss an opportunity to convey through the media how seriously her office takes such matters.

“USVI resident indicted for not registering as sex offender,” the headline in a local news outlet read.

That February 28th article was accompanied by a photo illustration that showed a parked auto with a driver-side front door emblazoned with the words “SEX OFFENDER In This Car.” It also pictured a house with a sign out front reading, ”SEX OFFENDER LIVES HERE.”

On April 12, Cole entered into a plea deal where he faces a sentence of no more than a year.

“St. Thomas Resident Pleaded Guilty to Failing to Register as a Sex Offender,” the U.S. Attorney’s press release announced.

In the meantime, on March 15, the other Jeffrey flew into St. Thomas aboard his private jet. He made his annual check-in at the local sex registry office, a gesture that can now be seen as a kind of mockery, as it’s been revealed that he had been seen still bringing young girls to his private island.

“Everybody was like, ‘Oh, yeah, that’s pedophile island,’” remembers a Wall Street numbers cruncher turned pizzeria owner who arrived in the Virgin Islands from New York in 2009.

Where were the authorities when it came to this Jeffrey?

Epstein’s Coney Island Days: From Math Nerd to ‘Arrogant’ Prick

At least four members of the local legislature accepted significant campaign contributions from Southern Trust Company, Inc., one of a host of business entities Epstein founded in the Virgin Islands. Those companies began with L.S.J, LLC, through which he bought his private island for $7.95 million in 1998.

Epstein had hired Cecile de Jongh, wife of former Virgin Islands Gov. John de Jongh, as the office manager for Southern Trust, which was granted income tax breaks of up to 90 percent by the U.S. Virgin Islands Economic Development Authority. The former first lady also managed the Epstein VI Foundation, which supported everything from brain research at Harvard to the girls’ volleyball team at St. Croix Central High School in the Virgin Islands.

After Epstein was arrested in Florida for a sex crime involving a minor, a Virgin Islands newspaper called The Avis ran an article suggesting that Cecile de Jongh’s connections with Epstein might muddy her husband’s political prospects. The Avis also noted that the arrest called into question whether the girls’ volleyball team should have jerseys bearing the name Epstein.

A purported grassroots movement collected 5,000 signatures on a petition accusing The Avis of yellow journalism. Epstein attorney Gerald Lefcourt issued a statement saying, “The grand jury and the prosecutor's office... determined that no serious offense had occurred.”


Epstein kept partying on Pedophile Island. He is said to have met some resistance when he sought to buy the nearby, larger island of Great St James. The blue-blood Danish family that owned it is said to have been reluctant to sell to someone with Epstein’s unsavory reputation. But he appears to have managed to acquire it anyway in 2016 by cloaking the buyer’s identity with a company called Great St. Jim LLC. He is said to have paid $18 million.

Epstein immediately applied for a permit to erect two 80-foot flag poles, arguing that the 45-foot limit on the books should not apply to his property. No doubt at least one of the poles would be used to fly an American flag and announce for everyone to see when the owner of Pedophile Island was back.

But construction of a compound on the bigger island was delayed by environmental concerns that even somebody as well-connected as Epstein could not just circumvent.

And there was far greater trouble brewing for Epstein as the result of a determined reporter, Julie Brown of the Miami Herald.

Brown revealed and documented the unconscionable plea deal Epstein had been granted. The Manhattan U.S. Attorney launched a new investigation.

In reviewing the 2007 Florida case, the FBI noted a court document reporting an incident that when agents served Epstein’s personal assistant Lesley Groff with a grand jury subpoena, she excused herself, purportedly to check on her child. She is said by the court document to have used the moment to telephone Epstein, who was headed in his private plane from Palm Beach to Teterboro Airport in New Jersey across the Hudson River from New York. He was in the company of another assistant, Nadia Marcinkova, who has been accused of complicity in his sex trafficking.

“Mr. Epstein became concerned that the FBI would try to serve his traveling companion, Nadia Marcinkova, with a similar grand jury subpoena,” the document reports. “In fact, the agents were preparing to serve Ms. Marcinkova with a target letter when the flight landed in Teterboro. Mr. Epstein then redirected his airplane, making the pilot file a new flight plan to travel to the US Virgin Islands instead.”

The American flag no doubt again went up over Pedophile Island as the FBI stood thwarted at Teterboro.

A dozen years later, the FBI took great care that Epstein received no warning. He flew unsuspecting on July 6 from Paris to Teterboro and a waiting pair of handcuffs.

On July 8, Epstein was arraigned in Manhattan federal court on charges of trafficking in underage girls. He was remanded as a flight risk and a danger to the community. He was consigned to the Metropolitan Correctional Center, briefly in general population but within hours assigned to the Special Housing Unit due to threats from inmates who apparently take a dim view of “short eyes,” as child molesters are known behind bars.

Epstein must have considered the arrest a possibility, for some time ago he commissioned an artist to paint a mural in his Manhattan mansion of him in a prison yard. Neither he nor the artist seem to have foreseen that he would find himself locked up 23 hours a day in an eight-by-eight foot cell infested with cockroaches and rodents. A thickly screened single narrow window faces a brick wall and lets in only enough light to tell night from day. Mold is said to grow on the walls. Water seeps in under the door from a shower to which he has access only once every three days.

For two weeks, Epstein’s cellmate was an ex-cop named Nicholas Tartaglione, who is accused of a quadruple murder. Tartaglione says the two became “friends,” whereby he joined a list that once included two presidents, Donald Trump and Bill Clinton. A realtor who asked not to be identified recently told The Daily Beast that Trump exclaimed at a business gathering at Tavern on the Green some years ago that Epstein was “my best friend.”

Tartaglione has reportedly told authorities that he saved Epstein from a suicide attempt. But Trump may not be the only liar on Epstein's list of pals. Tartaglione ended up in the Special Housing Unit after he was caught with a cellphone that he insisted had just been given to him by another inmate. Tartaglione then moved to keep the government from inspecting the phone’s contents on the grounds it may have privileged communications with his lawyer and with his wife. Never mind it was supposedly not his.

Epstein is now said to be on suicide watch. He is 66 and, if convicted, he stands a good chance of dying in prison even if he takes the best possible care of himself. He may have finally landed in a situation where all his money cannot save him from suffering the consequences of his actions.

Also behind bars is the other Jeffrey, having been remanded when he entered his guilty plea in April.

Cole had been free on his own recognizance since his arraignment, the court having deemed him to be neither a flight risk nor a danger to the community. His attorney petitioned for him to remain at liberty pending sentencing, which is set for August 15.

The attorney noted that Cole is a 57-year-old graduate of Ohio State University with a Bachelor of Science degree in landscape architecture, had been steadily employed for more than 30 years and was presently a fleet manager at a car rental company. He would be able to continue working there until his day of reckoning.

The judge remanded Cole nonetheless. Cole was shipped off to the Metropolitan Detention Center in Guaynabo, Puerto Rico. His attorney has since filed a motion to expedite matters.

“The current sentencing date inevitably results in a period of incarceration of four months,” the petition noted, adding that Cole was eligible to receive probation and no time at all.

As of Saturday, the sentencing was still set for August 15. Cole remains behind bars in Guaynabo. But he will almost certainly be free within the next few months.

And you can bet that this Jeffrey would not trade places with the other one for all the money in the world

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