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Former Jacksonville investment adviser charged with $2.7 million fraud

The indictment happened almost a year after the SEC told a judge Jared Eakes was “actively concealing his whereabouts."

JACKSONVILLE, Fla. — A one-time Jacksonville investment adviser is facing fraud charges involving $2.7 million of clients’ money after almost two years of financial regulators trying to find him.

Jared Dean Eakes, 32, was indicted last week on four counts of wire fraud affecting 17 clients from states including Alabama, Arkansas, Florida and Missouri. The charges include a demand for Eakes to forfeit the $2.7 million the government says he "personally obtained from the charged scheme."

The indictment happened almost a year after the U.S. Securities and Exchange Commission told a judge Eakes was “actively concealing his whereabouts” as the commission pressed a 2022 civil lawsuit accusing him of misusing client money to fatten his own brokerage accounts, pay off debts including his student loan bills and send $116,000 to a Las Vegas casino.

The former Merrill Lynch stockbroker had launched his own company, GraySail Advisors LLC, in 2018 and had been dogged since 2020 by investigations into his business, which listed an office on the 25th floor of downtown's Bank of America tower at 50 N. Laura St.

Court records said Jared Dean Eakes listed an address at the Bank of America Tower at 50 N. Laura St. downtown, shown here in a 2016 photo, as the office of his investment advisor business, GraySail Advisors, LLC.

The SEC lawsuit said that GraySail, which reported managing just $10 in assets, signed a deal in 2019 to take over an investment adviser business in Dothan, Ala., managing $43 million in accounts for about 150 clients.

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The takeover was never completed but the deal did move some clients to GraySail, and the SEC said Eakes stole about $2 million from 10 clients.

He did this, the SEC said, by forging promissory notes from another business; cutting and pasting clients’ signatures as evidence the clients bought the notes; then filing the fake paperwork with a firm managing clients’ Individual Retirement Accounts to have payments for the notes sent from the IRAs to the business’s bank account and then released to Eakes.

An FBI agent’s criminal complaint filed in April said the business getting payments for Eakes, Small World Capital LLC, was owned by a Jacksonville man who reported that Small World “never had any substantive business activities and its bank account was primarily used to transfer funds on behalf of Eakes,” whom Small World’s owner said he’d met through a mutual friend. The company was administratively dissolved as inactive in 2020, according to state records.

Eakes told the company owner where to send money that materialized in the owner’s bank account, the complaint said.

The complaint also described an Alabama woman, identified only by her initials, who said that in 2019 she had handed six checks totaling about $244,000 to the investment adviser in Dothan who had signed a deal with Eakes. The complaint said the woman wanted that adviser to open a retirement account and manage it for her but the money ended up in Eakes’ personal bank account and no retirement account was created. Eakes’ bank account was later emptied, the complaint said.  

The SEC’s lawsuit never went to trial because the commission said it could never find Eakes to serve paperwork on him, even when it hired an investigator who went to his family’s old address in Tennessee and found people there inside a garage who waved him away and closed the garage door on him, according to court records. Instead, a default entry was recorded in Jacksonville’s federal court on April 18.

The FBI agent looking into Eakes arrested him a month later, court records show.

This story first appeared on First Coast News partner The Florida Times-Union.

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