Although the new suit was brought by Mariano alone, Kasowitz Benson was already facing a lawsuit brought by Patriot. The company, represented by the same plaintiff's attorney, William Scherer, alleged in a June lawsuit that the firm engaged in fraudulent billing, malpractice and other misconduct that cost the company millions of dollars in damages. After a Florida judge ruled in August that the complaint could move forward, Kasowitz Benson vowed to appeal.

The new lawsuit filed in Florida stems back to 2014, when Mariano hired Simpson Thacher to handle Patriot National's initial public offering. That offering raised $141 million in January of 2015. According to the complaint, the law firm continued to do work for the company and when Mariano contacted the firm to raise more capital later in 2015, it paired the company with "predatory" hedge fund investors who engaged in "market manipulation" that threw the stock price into a "death spiral." That, in turn, threw Mariano and his company into litigation with the funds and other investors who were capitalizing on the crash of its stock price, the complaint said.