‘Annuity King’ faces a second trial on tax evasion charges

Image shows a crown against a blue sky backdrop and the words "tax evasion." — Phillip Roy Wasserman next faces tax evasion charges.

By John Hilton

Phillip Roy Wasserman's legal troubles did not end with his May 15 conviction on nine fraud counts. The self-styled 'Annuity King' will be tried separately on tax evasion charges.

Wasserman requested that the tax charges be severed from the fraud charges, court documents say. The government claims Wasserman, 66, with Kenneth Rossman, lied and concealed information to convince elderly victim-investors to put their money into Wasserman’s life insurance venture called, “FastLife.”

The government claims the fraud totaled $6.3 million, money it seeks to collect from Wasserman. Prosecutors are also focused on tax evasion.

"The evidence also established that Wasserman took numerous affirmative steps to evade payment of more than $900,000 in taxes due and owed," said U.S. Attorney Roger B. Handberg, representing the Middle District of Florida.

During a status conference Wednesday, Judge Charlene Edwards Honeywell estimated that the second trial will last two-to-three weeks. She also requested that Wasserman file a waiver of his right to a speedy trial by June 7.

Wasserman filed separate motions for acquittal and a new trial on his fraud conviction. The government has until the last week of June to file responses, court documents say. Finally, Wasserman's sentencing hearing was pushed back from Aug. 17 to Sept. 6.

Wasserman was convicted on nine fraud charges. The three most serious – wire fraud, mail fraud and conspiracy to commit wire and mail fraud – all carry maximum sentences of 20 years.

In July 2021, Rossman accepted a plea deal. According to court documents, Rossman 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." The two counts carry a maximum of eight years behind bars.

Rossman is scheduled to be sentenced July 12.

Spent clients' money, says U.S. attorney

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 news release said.

"Moreover, Wasserman 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," the release said.

"In a further effort to thwart the investigation, 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. 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."

InsuranceNewsNet Senior Editor John Hilton 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.

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.