At the request of the V.I. Justice Department and his attorney, David Whitaker has a new sentencing date, but exactly why is unclear as the motion seeking the change has been partially redacted “to protect sensitive information,” and a separate motion by the DOJ remains filed under seal for now.
Whitaker, the former owner of a cybersecurity company that did business with the V.I. government and became the focus of an FBI investigation, admitted to two counts of wire fraud and one count of bribery concerning programs receiving federal funds in a plea deal with prosecutors unsealed last month in V.I. District Court.
His sentencing hearing had been scheduled for Dec. 4 on St. Thomas, but on Friday the DOJ and Whitaker’s attorney David Cattie filed a joint motion to continue the hearing “to a date no sooner than September 1, 2025,” and requested that all deadlines associated with his sentencing be extended accordingly.
Judge Mark A. Kearney granted the request, in part, without prejudice and rescheduled the hearing to April 7, leaving open the possibility that a further extension could be granted “upon showing good cause.”
Additionally, the DOJ filed a motion for leave to file a sentencing document under seal.
Both parties now have until Wednesday to file memorandums “demonstrating particularized harm from disclosures” in that document — beyond two redacted sentences that are included in the separate motion for the extension of time — before restricting public access to the remainder of the document, Kearney ruled.
Kearney, a Third Circuit judge out of Philadelphia, was assigned to the case in September, replacing V.I. District Court Chief Judge Robert Molloy, which is not unusual in matters concerning the territorial government and its agencies.
The FBI investigation into the V.I. government’s contracts with Whitaker came to light in June, when agents seized the cell phones of then V.I. Police Commissioner Ray Martinez and Office of Management and Budget Director Jenifer O’Neal, who was subpoenaed to testify regarding the VIPD contract with Whitaker, the FBI and U.S. Attorney’s Office said at the time. Both Martinez and O’Neal resigned.
According to his partially redacted plea agreement, Whitaker’s bribery charge concerns money and favors he gave to a VIPD official identified as “Public Official One” in return for payment of outstanding invoices under his cybersecurity contracts with the department.
The bribes included financial assistance to a restaurant owned by a person whose name is redacted, in return for making sure Whitaker’s company’s outstanding VIPD invoices would be paid. In all, Whitaker provided at least $66,000 worth of bribes, including the purchase of restaurant supplies and equipment, trips from St. Thomas to Boston, and payment of cash to the person’s family, the plea agreement states.
One wire fraud charge stems from 12 surveillance devices Whitaker claimed to have found in V.I. government offices in a sweep he was hired to conduct in 2022 after a miniature spy camera was discovered at the Division of Personnel. In fact, he had planted them, according to the plea deal. He then billed the VIPD $130,195.10 for his “work.”
The other wire fraud count relates to false statements Whitaker made to the Small Business Administration to secure a potentially forgivable Paycheck Protection Program loan for $469,903 in February 2021, it said. The PPP was meant to help small businesses keep their workforces employed during the COVID-19 pandemic.
A pre-sentence investigation is underway. However, according to the plea agreement, the bribery count carries a maximum of 10 years in prison and the wire fraud charges up to 20 years behind bars. Each charge also carries a $250,000 fine. Whitaker also could have to pay the government anywhere from $196,195 to a maximum of $666,098 if it is unable to recover the proceeds of his crimes, the deal states.
Whitaker is currently free on an unsecured $250,000 bond, has surrendered his passport and was ordered not to travel outside of Georgia, where he currently lives, except to visit his father in Coeburn, Virginia, or to attend court hearings in the U.S. Virgin Islands.
His long history of fraud has raised questions about how he was able to land government contracts worth more than $3 million. According to an expose of his escapades by Wired magazine in May 2013 that called him a “career conman,” Whitaker has been in and out of jail since he was first arrested for bank fraud and e-racketeering in 1997 when he was 22.
In 2008, he was nabbed in Mexico and returned to the United States to face a multicount fraud complaint of bilking customers out of more than $10 million by selling, but never delivering, electronic equipment. While on the lam south of the border, he allegedly made millions of dollars by selling black-market steroids and human growth hormones online. Facing 65 years behind bars on the fraud charges, Whitaker became an FBI operative in a sting that eventually saw Google fined $500 million for its role in facilitating online illegal drug sales. Whitaker subsequently got five years on the fraud charges.
