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An island manager for Jeffrey Epstein asked the disgraced financier and convicted sex offender for more than $50,000 to fund her two teens’ tuition at North Broward Preparatory School in 2015, according to the most recent United States Department of Justice (DOJ) file release concerning Epstein’s personal and business dealings.
Emails and billing records exchanged among school officials, Epstein, and a woman identified in email signatures as Ann Rodriguez, who appears to have served as general manager of Little St. James Island (listed in email signatures as LSJE, LLC), indicate that Epstein financed — or in some instances extensively discussed covering — tens of thousands of dollars in expenses. These included plane trips, visits to a dude ranch, and potentially, boarding school tuition for two girls identified in the correspondence as Rodriguez’s daughters, Sierra and Emery Poleon. Sierra’s name appears dozens of times throughout the files, while Emery is mentioned only a couple of times.
Emails between Sierra and Epstein, in particular, appear to show a filial relationship between her and the convicted sex trafficker.
This is far from the first revelation of Epstein’s South Florida connections. In 2008, he served 13 months in Palm Beach County Jail under a nonprosecution deal that involved a work release during the day. As part of the deal, which allowed Epstein to avoid more serious federal charges, he had to register as a sex offender.
There are several email exchanges between Rodriguez and Epstein about travel arrangements for her and her two daughters, including flights across the country and discussions about tuition totaling tens of thousands of dollars for the girls.
In a trove of emails from 2015, years after Epstein’s child prostitution conviction, Rodriguez chats with him about paying more than $50,000 in tuition for her daughters to attend North Broward Preparatory School in Coconut Creek (in the northern part of Broward County).
A statement from the school dated May 15, 2015, shows a $3,000 deposit for each student. The statement also shows a tuition fee of $26,625 for each student, marked as installment one of two. An email from Rodriguez to Epstein confirms he covered the $6,000 deposit for the girls.
It’s unclear whether Epstein ever paid the remaining $53,250 in tuition for Rodriguez’s daughters to attend North Broward Preparatory School.
While the emails don’t confirm whether the girls attended the school, a message from Rodriguez to Epstein mentions a seven-hour student shadowing appointment on a Monday in April 2015.
“Hey Bossman,” Rodriguez writes in the email, relaying to Epstein her and her daughters’ schedule for the visit, as well as their travel itinerary and costs (totaling $1,700). “Thank you again for everything,” she concludes, “Ann R.”
North Broward Preparatory School officials didn’t return New Times’ requests for comment via email or phone.
The paper trail between Rodriguez and Epstein regarding the girls’ attendance at the Broward County school appears to go cold in 2015, but subsequent emails allege that he paid about $11,000 for the girls to attend a summer camp near Lakeland, in Central Florida, called Circle F Dude Ranch, in June 2015.
“Hey Bossman, The girls will be leaving for summer camp ‘Circle F’ on June 21st – August 1st,” Rodriguez writes to Epstein. “Do I have your permission to forward the balance to Rich to pay by Wire?”
Epstein responds with a simple “yes.”
Two years later, in 2017, Sierra began emailing thank-you notes and holiday wishes to Epstein.
In November 2017, Sierra writes, “Hi J=ffrey thank you for giving my sister and I money and the opportunity to co=e to this school. I am struggling a little but with school but I =rying to work on that I just wanted to email you and tell you thank you fo= everything that you done for us but thank you again so much Jeffrey=and I miss you.”
A reply from Epstein a few hours later reads, “keep up the good work, we are all proud of you both.”
In a June 2018 email, Sierra writes, “Happy Father’s Day =Jeffrey hope you had a good day.”
He responds with, “thx and you have done really well.”
In a January 2019 email, six months before his July 2019 indictments for charges of sex trafficking of minors in Florida and New York, Sierra writes, “Please Jeffrey I never felt unsafe until today I am going to die. Sierra.”
It’s unclear to what situation Sierra was referring, but Epstein, in his reply, mentions a cryptic agreement. “You broke our agreement,” he writes. “You can leave if you=want. If you do I can no longer help. Your choice.”
Florida court records filed this month indicate that Sierra is still alive.
