‘Annuity King’ gets trial date for lawsuit against feds, Florida regulators

Image says, "Annuity King Civil Suit" — Phillip Roy Wasserman claims agents had biases when they investigated his annuity business.

By John Hilton

Phillip Roy Wasserman is expected to get another day in court to make his case that state and federal agents broke the law during investigations that led to his fraud conviction.

Wasserman was convicted on May 15, 2023, on nine felony counts. The three most serious – wire fraud, mail fraud and conspiracy to commit wire and mail fraud – all carried lengthy prison terms. The self-styled "Annuity King" in Florida promotions, Wasserman ran a fraud totaling $6.3 million, the government alleged, money it seeks to recover.

Wasserman, 68, is behind bars at Coleman Low Federal Correctional Institution in Sumterville, Fla., according to the Bureau of Prisons. His release date is June 5, 2036.

Meanwhile, Wasserman filed a civil lawsuit in 2021 against the United States, the Florida Department of Financial Services, and Stephen Howland over alleged bias in their investigations into Wasserman's business.

Judge Thomas P. Barber scheduled a pretrial hearing for 1:30 p.m. Aug. 18, with the trial set for the Sept. 3 trial term.

Wasserman: Rampant bias

Wasserman makes several claims of bias in the state and federal investigations. He claims that state officials have a politically motivated vendetta against him because of his successful efforts to oppose the U.S. Senate campaign of Betty Castor in 2004.

Howland is named because he was a financial investigator for the Florida Office of Financial Regulation from 2014 to 2021. Wasserman had a history of financial problems that resulted in various tax liens and civil judgments being entered against him and his companies, Howland noted in court documents.

"Plaintiff claims that his history of tax liens and adverse civil judgments somehow show that OFR and Investigator Howland were out to get Plaintiff; however, such is without merit," former Florida Attorney General Ashley Moody wrote in a court response. "If anything, Plaintiff’s history of tax liens and adverse civil judgments provided further justification for OFR’s and Investigator Howland’s investigation."

Likewise, federal agents discussed Wasserman's tax liens and civil judgments during interviews with clients and potential witnesses, Wasserman claims. Agents asked leading questions, Wasserman alleges, such as, "Did you know that Wasserman paid himself a salary of more than $500,000 per year?”

"Questions in this format ... is clearly telling the interviewees this is what Wasserman did, even though the premise of many of the questions was false and misleading," Wasserman claims in court documents.

Government: FastLife fiction

The government said Wasserman, with Kenneth Rossman, lied and concealed information to convince elderly victim-investors to put their money into Wasserman’s life insurance venture called, “FastLife.”

Despite facing a sentencing range of 30 to 37 months, Rossman was sentenced to probation. He pleaded guilty to one count of conspiracy to commit mail fraud and wire fraud, and one count of "aiding and assisting the preparation and filing of fraud and false tax returns" in a plea deal with the federal government.

Rossman testified against Wasserman as part of the deal.

The government requested a stiff sentence for Wasserman, claiming that he urged one witness to lie to investigators, attempted to dissuade several victim-investors from cooperating with law enforcement, and requested that one victim-investor make a baseless complaint against an investigator.

In addition, Wasserman falsely and fraudulently represented that he had an audit from a highly regarded financial services firm that would show neither he nor FastLife had committed any wrongdoing, the government said.

"In fact, Wasserman had never even engaged the firm to perform an audit and never received any final work product of any kind from the firm," a news release said.

Wasserman spent "a significant amount of the victim-investors’ money" to finance a lavish lifestyle that included a luxury personal residence, a beach house on Casey Key, Tampa Bay Lightning season and playoff tickets, concerts and other shows, vehicles, jet skis, jewelry, personal celebrity entertainment, gambling, retail shopping, home improvements, personal insurance, and a host of other expenses for his personal benefit and the benefit of family members, the U.S. attorney's office has said.

InsuranceNewsNet Senior Editor John Hilton has covered business and other beats in more than 20 years of daily journalism. John may be reached at [email protected]. Follow him on Twitter @INNJohnH.