A few years before the more-recent spate of Florida insurance carrier insolvencies, a workers’ compensation insurer known as Guarantee Insurance Co. was declared insolvent in 2017—a rarity in the usually profitable workers’ comp line of business.
Regulators blamed owner Steve Mariano for diverting more than $15 million and using the funds for “no discernible business purpose,” something Mariano has disputed. News reports and lawsuits at the time raised questions about the entrepreneur’s purchase of a multi-million-dollar mansion, a condominium and a yacht in south Florida.
A few months later, the Fort Lauderdale insurance technology and back-office and underwriting services firm, Patriot National, whose largest customer was Guarantee and whose CEO and majority owner was Mariano, filed for bankruptcy. The collapse came just three years after Patriot National went public on Wall Street, raising more than $140 million from investors.
It was a stunning and sudden downfall that made headlines for years and is still ringing through courthouses in Florida. Since the Chapter 11 bankruptcy filing, Mariano has blamed his auditors, Wall Street investment funds, and large national law firms for the demise of Patriot National.
On Tuesday, July 14, a long-delayed jury trial in Mariano’s malpractice lawsuit against the law firms of Simpson Thacher & Bartlett, and Kasowitz Benson Torres, which advised and facilitated on the IPO in 2014 and subsequent fundraising and litigation, is set to begin in Broward County Circuit Court in Fort Lauderdale. The trial promises to make for some new revelations and perhaps provide some guideposts for insurance companies and insurtech firms considering going public.
Mariano’s lawsuit was initially filed in 2018, but has met with years of delays, motions to dismiss, changes of attorneys, calls for sanctions, and more. The 172-page complaint argues that instead of looking out for Patriot National’s best interest in raising new capital in 2015, Simpson Thacher paired Mariano with “predatory hedge fund investors” who engaged in market manipulation “that placed Patriot National into a death spiral and threw both Patriot National and Mariano into major litigation with the hedge funds and other opportunistic claimants seeking to capitalize on the crash of Patriot National’s stock price.”
The New York-based Simpson law firm is well known for handling other major Wall Street deals through the years, including the famous Kravis Kohlberg Roberts $25 billion acquisition of RJR Nabisco in 1988. But for Patriot National, the white-shoe law firm failed to draft non-disclosure agreements and securities purchase agreements that would have protected Patriot National from the hedge funds’ alleged actions, the lawsuit complaint charges.
“After getting fleeced by the hedge funds in a transaction that doomed Patriot National and thrust both Patriot National and Mariano into litigation, Simpson Thacher made matters worse by directing the litigation work to one of its alumni who would not be likely to criticize Simpson Thacher’s handling of the transaction and who proceeded to cause further damage to Patriot National and Mariano by negligently preparing Mariano’s affirmative defenses without pleading readily available facts supporting Mariano’s available defenses to the hedge funds’ claims,” the complaint reads.
That Simpson Thacher alumnus was at the time an attorney with Kasowitz, a New York firm with offices in Miami. The Kasowitz firm put its own interests above Mariano’s, failed to advise him of potential claims against Simpson Thacher, and failed to properly defend him in litigation brought by the hedge funds, the suit charges.
“As a result of the actions of both Simpson Thacher and Kasowitz, Patriot National’s business was decimated, laying off 250 employees in Fort Lauderdale and declaring its intention to enter Chapter 11 bankruptcy in November 2017, and Mariano has been personally embroiled in expensive litigation over Patriot National’s demise,” Mariano’s complaint alleges.
He and Patriot National are now represented by the Fort Lauderdale-based law firm of Conrad & Scherer and other lawyers. The suit asks for more than $200 million in damages, according to news reports.
Simpson Thacher and Kasowitz attorneys have denied Mariano’s allegations, calling the long-running lawsuit “meritless” and “baseless.”
“The undisputed facts are far simpler: there was no market manipulation,” reads a Simpson Thacher 2025 motion for summary judgment. “The price of Patriot National stock fell in the wake of the sale because the market was ‘spooked’ that Mariano, the company’s CEO, had sold such a large stake at such a steep discount. Indeed, Mariano had been warned that his sale would cause ‘negative fallout’ in the market.”
That motion was denied by the judge in the case, as was a Kasowitz motion to dismiss.
Jury selection in the trial could begin begin Tuesday morning, with opening arguments set for Wednesday.
Topics Lawsuits
Was this article valuable?
Here are more articles you may enjoy.
Travelers Builds Insurance-Specific LLM 
New Jersey Busts Alleged $8 Million Auto Theft Operation Involving 63 People 
Allianz Unit to Cut as Many as 1,800 Jobs in Push to Adopt AI 
NYC to Publicly Identify Buildings Testing Positive for Legionnaires’ Bacteria 
