‘I committed zero crimes’: Unrepentant ‘Annuity King’ pursues appeals from prison

Phillip Roy Wasserman suffered another setback last week when a federal judge sided with Florida and federal investigators in his civil lawsuit.

U.S. District Judge Tom Barber awarded summary judgment to Stephen Howland, the State of Florida Office of Financial Regulation, and the federal government. Howland is a former financial investigator for the OFR.

Wasserman, the self-styled “Annuity King” who is serving a 15-year prison sentence for fraud, alleged that state and federal investigators misled witnesses with biased questioning in a vendetta against him.

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

The questioning was appropriate considering the circumstances of the investigations that overlapped fraud and tax charges, Barber said.

Fit and healthy

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

Wasserman recently reached out to InsuranceNewsNet and established communication via CorrLinks, a secure email system used by federal prisons to allow inmates to exchange monitored electronic messages with people outside prison.

A 13-minute phone call followed in which Wasserman discussed his case and life behind bars.

Wasserman gets up at 5 a.m. every day, gets plenty of exercise and has dropped about 60 pounds, he said.

“The food is surprisingly good,” he said. “They have a good library with a law center where we can do legal research on computers. No internet, of course, but access to Lexis Nexus. I work on my case about 50 hours a week.”

In addition to exercising and working on his case, Wasserman said he has written two mystery novels and enjoys weekend visits from his family. Inmates are allowed Saturday and Sunday visits twice a month, “usually two hours,” he said.

The lone negative at Coleman is a noticeable lack of funding, Wasserman explained. Overcrowding is a persistent problem and some inmates struggle with medical needs.

“It is not Mar-a-Lago,” he quipped. A one-time member of President Donald Trump’s exclusive Palm Beach club, Wasserman nonetheless said he has not reached out to the president’s orbit in search of a pardon.

“I have been focused on establishing my innocence,” he said.

New appeal filed

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. Wasserman allegedly ran a fraud totaling $6.3 million, which the government seeks to recover.

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.

On Wednesday, Wasserman said he is filing a new 33-page Rule 33 request for a retrial, “based on newly discovered evidence the prosecution hid.”

Wasserman remains unrepentant about what the government claims are elderly victims who lost crucial retirement savings.

"I committed zero crimes."

–Phillip Roy Wasserman

"Am I unhappy that my friends who were investors suffered damage as collateral? Five thousand percent," Wasserman said. "That's why, when I win my appeal, and I'm not obligated, I'm still going to use the proceeds from the civil suit to reimburse them. That's going to happen. But if you ask me, 'Do I have remorse for committing a crime?' I committed zero crimes."

Case details questioned

Frank E. Worrell spent 22 years investigating financial fraud with the Federal Bureau of Investigation. He is also a certified public accountant licensed in South Carolina and a private investigator with Quick Group in Mt. Pleasant, S.C. Worrell was part of Wasserman's defense team and said the evidence does not rise to the level of a crime.

Wasserman was trying to build a life insurance model similar to SelectQuote, for example, and his mistake was not being properly capitalized, Worrell explained. However, investors were aware that they were investing in an "unsecured" investment, he added.

The millions collected by Wasserman were put into advertising and payroll, Worrell noted. FastLife was a typical new business venture that lost money in its early years, he insisted, and the government did not allow the business to mature into something that might have worked.

The government 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, professional hockey season and playoff tickets, concerts and other shows, vehicles, jet skis, jewelry, including a diamond ring, personal celebrity entertainment, gambling, retail shopping, home improvements, personal insurance, and a host of other expenses.

Wasserman and Worrell say many of those expenditures can be justified. For example, the house was used as a training site for employees, Worrell said.

"It's not to say somebody who lent him money doesn't have some civil recourse or a case. That happens all the time," Worrell said. "But we're talking about a man's life. He's trying to do a venture, and he's now sitting in prison. For the life of me, I just don't see it. It's a heavy sentence for fraud. I cannot believe it."

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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.