U.S attorney alleges obstruction, seeks stiffer sentence for ‘Annuity King’

Government prosecutors are waging an escalating battle of obstruction charges against Phillip Roy Wasserman as a Florida judge prepares to sentence the former "Annuity King" on fraud charges.

U.S. Attorney Roger B. Handberg filed a presentencing report with the District Court for the Middle District of Florida detailing a lengthy list of obstruction allegations against Wasserman. Handberg asked Judge Charlene Edwards Honeywell to sentence Wasserman "at the high end" of the recommended 324-405 months.

Wasserman, 66, who took the "Annuity King" moniker in advertising, is slated to be sentenced Oct. 5.

Wasserman was convicted May 15 on nine felony counts. The three most serious – wire fraud, mail fraud and conspiracy to commit wire and mail fraud – all carry maximum sentences of 20 years.

The government claims Wasserman, along 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 both men. There are tax evasion charges as well in a second trial slated to begin this fall.

Multiple acts of 'obstruction' alleged

Handberg accused Wasserman of "numerous steps aimed at obstructing the investigation and later the prosecution of this case." Wasserman allegedly submitted false information and false testimony, Handberg said, and tampered with witnesses and repeatedly harassed and berated prosecutors.

Wasserman "sent emails to victim-investors that included characterizations of the investigators, clearly aimed as discrediting the investigators and, thereby, attempting to dissuade the victim-investors from cooperating with the law enforcement investigation," Handberg wrote. Wasserman called one agent a “Nazi scumbag” and white supremacist, he added.

Wasserman denies the allegations and said that out of more than 100 witnesses, he only ever spoke to one, when a man he knew came up to him in a casino.

"As for badgering prosecution attorneys, I guess they’re very sensitive when you call out a liar for being liars," he said.

In a response filed Monday, Wasserman addressed one allegation in the sentencing report: a pair of memorandums filed in December that included incorrect case citations. Wasserman claims he used artificial intelligence and create the documents and withdrew them "immediately" upon learning of the errors.

"To illustrate the absolute vindictiveness of the United States in this case, the government has used a knowingly innocent mistake that was immediately detected and rectified by Mr. Wasserman to move this Court to sentence Mr. Wasserman to a longer term in federal prison for obstruction of justice," the Wasserman response reads.

Wasserman asked the court to strike the reference to incorrect citations from the record.

Mental illness questions

Despite facing a sentencing range of 30 to 37 months, Rossman was sentenced to probation last month. 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.

In its presentencing report, the government defended seeking a stiff sentence for Wasserman while supporting Rossman's light punishment. Rossman cited a bipolar disorder in arguing for a lighter sentence.

Rossman's bipolar admission was never fully explored at trial, Wasserman said. In an August 2021 motion, Wasserman's attorneys asked the court to compel Rossman to take a psychiatric exam before he testified. A judge rejected that motion.

"The only clear obstruction of justice that has happened in this case is the government failing to notify the Court and Defendant of Mr. Rossman’s mental illness after outright accusing Defendant of committing another federal crime of witness intimidation by filing a motion to compel his medical records and asking this Court that Mr. Rosman to sit for an independent medical examination," Wasserman wrote in Monday's brief.

InsuranceNewsNet Senior Editor John Hilton covered business and other beats in more than 20 years of daily journalism. John may be reached at john.hilton@innfeedback.com. Follow him on Twitter @INNJohnH.

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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 john.hilton@innfeedback.com. Follow him on Twitter @INNJohnH.