Sarasota's 'Annuity King' sentenced to 15 years for defrauding seniors

Phillip Roy Wasserman, a Sarasota insurance agent and former attorney who called himself the "Annuity King," has been sentenced to 15 years in federal prison for scamming millions from elderly victims.

The 67-year-old was also ordered by U.S. District Judge Charlene Edwards Honeywell to forfeit $6.3 million at a sentencing hearing this week in Tampa.

Wasserman was convicted by a jury in May 2023 of bilking senior citizens out of millions and using the money to buy a luxury home, Tampa Bay Lightning season tickets, jet skis and assorted other items for himself and his family. He was found guilty of nine counts, ranging from wire fraud to issuing false statements to lying to investors about the state of his company and previous financial problems.

He then pleaded guilty to tax evasion in October.

This case was investigated by the IRS' criminal investigation division and the Florida Office of Financial Regulation. Assistant United States Attorneys Rachelle DesVaux Bedke and Rachel K. Jones were the prosecutors. 

In a Thursday news release, Brian Payne, a special agent in charge with the IRS, says that Wasserman exploited “the most vulnerable in our society” with false promises and that investment schemes targeting the elderly will not be tolerated.

“Wasserman called himself the Annuity King, but his actions and crimes have earned him another name: Convicted Felon.”

According to a superseding indictment filed in June 2020, statements from the Office of the U.S. Attorney for the Middle District of Florida, previous reporting by the Business Observer and other court papers, this is what happened:

Wasserman was selling insurance and annuity products through his firm Phillip Roy Financial Consultants when, sometime around 2016, he created an insurance venture called FastLife. According to a website for FastLife that remains up, the company sought to generate retirement income for those who bought annuities.

Prosecutors, however, called FastLife a “fraudulent insurance venture.”

As part of the scheme, Wasserman brought in Kenneth Rossman, a CPA and also a licensed insurance agent. Together, the men conspired to get their mostly elderly clients to put money into this new venture. The pair convinced some of these investors to liquidate other investments and to borrow against life insurance policies to generate cash to invest into FastLife. This without telling them they’d be charged surrender fees and other charges for liquidating investments or about the tax implications of cashing out early.

The indictment says the investors were promised an annual return of 10% to 12%, which was much higher than they received from other investments, and that they would get monthly interest payments which they could also reinvest and receive the money at maturity. In order to keep the scheme alive, the men lied to investors when pushed about not being paid and created false investor statements showing false balances and earnings.

The investments, victims were told, would be used to pay for expenses and grow the business.

But in fact, Wasserman paid Rossman a percentage of the money invested as compensation for his role in the conspiracy. And he used the money to make payments to earlier victims and creditors.

Rossman pleaded guilty in 2021 and was sentenced to five years of probation last year.

While prosecutors don’t out-and-out call what happened a Ponzi scheme, in the superseding indictment they call the money going to early investors “Ponzi-style payments.” (A Ponzi scheme is when people pay into a fraudulent investment and their money is used to pay previous investors.)

The money also went to fund Wasserman’s lifestyle, including a beach house on Casey Key, Lightning season and playoff tickets, concerts, high-end vehicles, jewelry, personal celebrity entertainment, gambling, home improvements and personal insurance.

Among other accusations are that Wasserman entered into TV and radio contracts and sponsorships to promote FastLife that were never paid, evaded payment of more than $900,000 in taxes and did not tell investors about a “multitude” of civil judgments and other debts.

During the trial it was also revealed he had created a second set of books and fabricated a compensation agreement to try to convince investigators he hadn’t used the money for personal use. He also urged a witness to lie to investigators, encouraged victims to not cooperate with the investigation and lied about an audit.