Wasserman v. United States

District Court, M.D. Florida·Decided September 8, 2025·No. 8:21-cv-02334·Unknown

Opinion

UNITED STATES DISTRICT COURT MIDDLE DISTRICT OF FLORIDA TAMPA DIVISION

PHILLIP R. WASSERMAN,

Plaintiff,

v. Case No. 8:21-cv-2334-TPB-SPF

UNITED STATES OF AMERICA, STEPHEN HOWLAND, and STATE OF FLORIDA OFFICE OF FINANCIAL REGULATION,

Defendants. ________________________________________/

ORDER ON CROSS-MOTIONS FOR SUMMARY JUDGMENT

This matter is before the Court on cross-motions for summary judgment, all of which were filed on December 13, 2024, by Defendants Stephen Howland, Defendant the State of Florida Office of Financial Regulation, Defendant United States of America, and Plaintiff Phillip R. Wasserman. (Docs. 77; 78; 79; 81). Responses to those motions were timely filed (Docs. 92; 94; 95; 97), as were replies to those responses (Docs. 102; 103; 104; 105). The Court also requested and received supplemental briefing from Defendant United States of America and Wasserman. (Doc. 117; 123; 124). After reviewing the motions, responses, replies, additional briefing, the court file, and the record, the Court finds as follows: Background Plaintiff Phillip R. Wasserman, a former member of the Florida Bar, is currently serving a 180-month federal prison sentence for fraud and tax evasion.1

After a thirty-day criminal jury trial, where he represented himself, Wasserman was convicted on one count of conspiracy and on numerous counts of wire fraud and mail fraud. He subsequently pled guilty to tax evasion charges. See United States v. Wasserman, 8:20-cr-00207-CEH-NHA (M.D. Fla. Feb 1, 2024) (Docs. 992; 1005; 1019). Even before he was convicted and sentenced to prison, Wasserman filed this civil action against some of the governmental enforcement entities and individuals

that worked on the criminal case against him. Wasserman’s criminal charges arose from his fraudulent activities in connection with FastLife, a life insurance brokerage firm that he started in 2016 with his criminal co-defendant, Kenneth Rossman. To get FastLife off the ground, Wasserman and Rossman obtained funds from numerous investors – many of whom were senior citizens with whom Wasserman and Rossman had no prior relationship. The investors loaned money to the company through promissory notes with varied

interest rates, and many were persuaded to liquidate traditional investments such as annuities to do so. But Wasserman and Rossman failed to disclose to investors the potentially negative personal tax consequences resulting from such liquidations, among other things.

1 The Florida Bar’s official website indicates Plaintiff is “not eligible to practice law in Florida,” apparently as a result of a “disciplinary resignation.” Member Profile: Phillip R. Wasserman, Fla. Bar, https://www.floridabar.org/directories/find-mbr/profile/?num=486388 (last visited Sep. 4, 2025). In 2018, the State of Florida Office of Financial Regulation (the “OFR”) began investigating Wasserman and FastLife for fraud after they received a tip from state officials in Alabama. Defendant Stephen Howland was assigned as the investigator

to oversee the case for the OFR. In reviewing public court records, Howland discovered several federal tax liens and adverse civil judgments against Wasserman. He also obtained information as to Wasserman’s compensation and expenditures through subpoenas issued by the OFR. Howland then began interviewing FastLife investors and inquired about: (1) Wasserman having any tax liens or civil judgments entered against him, (2)

whether they believed it would have been material for them to know about the liens and judgments before investing with FastLife, and (3) whether they would still have invested if they had known about the liens and judgments. Howland further asked the investors about their knowledge of Wasserman’s compensation agreement, as well as whether they were aware of how FastLife’s funds were being spent. In 2019, the United States, led by IRS Special Agent Shawn Batsch, joined the OFR’s investigation to review potential federal tax, fraud, and conspiracy

violations. Batsch and his team began conducting joint interviews of FastLife investors with Howland, inquiring about the tax liens and judgments, Wasserman’s obligations to investors, Wasserman’s comingling of business and personal funds, Wasserman’s lack of bookkeeping and tracking for investment funds, as well as asking if any of these facts would have changed their minds about investing. The investigation resulted in a federal criminal indictment, jury trial, conviction and Wasserman’s 180-month prison sentence. Before his criminal trial, however, Wasserman filed the instant action

alleging that in the course of interviewing witnesses as part of their investigation, Batsch and Howland improperly disclosed information related to Wasserman’s tax liens and judgments, compensation and authority over FastLife affairs, personal expenditures and debts, FastLife’s bookkeeping, and evidence that he was commingling business and personal accounts. See (Doc. 21). He alleges that these disclosures violated 26 U.S.C. § 6103, a federal statute that imposes liability for

unlawfully disclosing taxpayer return information. Wasserman seeks damages in the amount of at least $1,000 per disclosure, in addition to punitive damages for the alleged disclosures.2 Each Defendant answered the amended complaint and asserted several affirmative defenses. See (Docs. 23; 41; 42). Following discovery and a failed mediation conference in November 2024, the parties filed their respective motions for summary judgment.

Legal Standard Summary judgment is appropriate “if the movant shows that there is no genuine dispute as to any material fact and the movant is entitled to judgment as a matter of law.” Fed. R. Civ. P. 56(a). A properly supported motion for summary

2 While Wasserman brings a total of 70 counts against Defendants for improper disclosures of return information, they are premised on the same factual background – Wasserman separates these counts based on the recipient and subject matter of the disclosure. judgment is only defeated by the existence of a genuine issue of material fact. Anderson v. Liberty Lobby, Inc., 477 U.S. 242, 249 (1986). The moving party bears the initial burden of showing that there are no

genuine issues of material fact. Hickson Corp. v. N. Crossarm Co., 357 F.3d 1256, 1260 (11th Cir. 2004). When the moving party has discharged its burden, the nonmoving party must then designate specific facts showing the existence of genuine issues of material fact. Jeffery v. Sarasota White Sox, Inc., 64 F.3d 590, 593-94 (11th Cir. 1995). If there is a conflict between the parties’ allegations or evidence, the nonmoving party’s evidence is presumed to be true and all reasonable

inferences must be drawn in the nonmoving party’s favor. Shotz v. City of Plantation, 344 F.3d 1161, 1164 (11th Cir. 2003). The standard for cross-motions for summary judgment is not different from the standard applied when only one party moves for summary judgment. Am. Bankers Ins. Grp. v. United States, 408 F.3d 1328, 1331 (11th Cir. 2005). The Court must consider each motion separately, resolving all reasonable inferences against the party whose motion is under consideration. Id.

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