Robert Pressman, a third-generation member of the family that turned Barneys New York into a designer emporium and New York City institution, has filed a lawsuit alleging that his kin evaded millions in taxes by falsely claiming that their late mother lived in Florida.

Pressman’s attorney Randall M. Fox, a partner at Kirby McInerney LLP, said Thursday, “In this case, we are seeking in excess of $50 million.”

Pressman is taking action as “a whistleblower” under the New York False Claims Act, which authorizes citizens to bring lawsuits to recover treble (or triple) damages for fraudulent claims submitted to New York. If the case is successful and a recovery is made on behalf of the government, Pressman may recoup between 15 and 30 percent, according to Fox.

Pressman has taken action against the estate of his late mother Phyllis, the Phyllis Pressman Revocable Trust, the Fiduciary Trust International of the Southland and his three siblings Eugene [“Gene”] Pressman, Elizabeth Pressman-Neubardt and Nancy Pressman-Dressler. The claims are for income taxes and estate taxes for Phyllis Pressman, who died on April 16, 2024. The filing states that from about 2018 until her death, she was a New York domiciliary, and as such, was required to pay New York state personal income taxes. In addition, at the time of her death, her estate is a New York resident estate, which requires the payment of New York estate taxes.

Pressman , who is known as “Bob,” claimed that his brother and two sisters along with the trust and its trustee Fiduciary Trust “conspired to falsely claim” that Phyllis Pressman was a Florida resident, and not a New York one. Unlike New York, Florida does not have state-level personal income taxes or estate taxes. Bob Pressman alleged that Phyllis Pressman, the trust, the estate, and the fiduciary trust “made and used false documents, including tax returns, that asserted that Phyllis Pressman’s primary home was in Florida, and that she was not a New York resident,” in the filing. By about May 2021, “she had drawn the three adult children into her plan, and they became her knowing accomplices both during the last years of her life and after her death,” according to the filing.

Bob Pressman could not be reached immediately Thursday for comment, nor could his brother Gene or his sister Pressman-Neubardt. His other sister Pressman-Dressler deferred comment to her attorney Laurie Ruckel, managing partner at Loeb & Loeb LLP, who did not respond to media requests Thursday afternoon.

Fox said that based on Phyllis Pressman’s actions and statements, “it was clear that the mansion in Southampton was her permanent home. But for tax purposes, and obviously that’s what we’re claiming, she indicated that Florida was her permanent home, even though she told other people that she hated Florida,” he said.

The siblings have wrangled in court off and on through the years. In 1999, Robert Pressman was hit with a $30 million lawsuit that was filed by his sisters. The suit also sought $10 million in punitive damages, with the sisters alleging that he took more than his share of the family business without their permission by engaging in “self-dealing, misrepresentation and fraud.” In August 2002, New York State Court Justice Karla Moskowitz awarded the two sisters — Pressman-Neubardt and Pressman-Dressler — $11.3 million, which was comprised of $7.3 million in damages and $4 million in pre-judgment interest. Robert Pressman then appealed the decision and countersued, alleging “fraud, self-dealing and unjust enrichment.”

Gene Pressman had also served as co-chief executive officer and creative director at Barneys. Each family member pitched in with the family business and became more involved as their parents aged. Under Fred Pressman’s leadership, Barneys expanded from a mom-and-pop menswear shop in the Chelsea section of Manhattan into an internationally renowned chain with 14 stores and seven outlets in the U.S. and a volume of $425 million for the year ended July 1995. The couple and their offspring abided by the mantra “Select. Don’t settle.” The company was started in 1923 by Fred Pressman’s parents Barney and Bertha.

After evolving from a 500-square-foot discount men’s store in Chelsea into a directional multistore retailer, the company expanded beyond New York with outposts in Seattle, Chicago, Los Angeles, Las Vegas and Boston at one point. In the late 1980s and 1990s, Barneys’ 10-story Madison Avenue flagship was the main attraction, where celebrities, politicians, New York City power players, and fashion-loving shoppers could be found combing through the minimalist-designed store or breaking bread at the buzzy restaurant “Fred’s.” In 2019, Barneys filed for Chapter 11 bankruptcy protection. That marked the second time that the slick specialty store had filed Chapter 11 with the first time having taken place in 1999.

Pressman’s filing described how his mother was an integral part of the family “that turned the Barneys retail store in Manhattan into the luxury international retailer Barneys New York.” It also noted how Pressman’s husband of 47 years, Fred, “led the effort to develop the business” that was founded by his father Barney in 1923 at Seventh Avenue and 17th Street in Manhattan. The lawsuit credits Phyllis Pressman with taking part in that effort by “taking on the responsibility for the ‘look’ of the store and developing Barneys’ home decor, antiques, jewelry, and other luxury merchandise business with the introduction of ‘Chelsea Passage.’ She was renowned for her exacting and highly developed taste and sophistication.”

Asked if Phyllis Pressman was of sound mind later in life, Fox said, “Perhaps, I don’t know about the entire period.”

As for whether there was a point where another individual was acting on her behalf due to her mental capabilities, Fox said, “Nobody has publicly said [that.]”

Meanwhile, Freeman’s | Hindman plans to go forward with this fall’s five sales that will feature “Property from the Collection of Phyllis and Fred Pressman.” Jewels from Bulgari, Harry Winston and Van Cleef & Arpels will go under the gavel, as will furniture and art from Frederick Carl Frieseke, Edward Henry Potthast and William Merritt Chase, among others.

Asked if the latest Pressman lawsuit will impact those plans, Thomas Brown, a spokesperson for Freeman’s | Hindman, said Thursday, ”The sale reflects the full and finalized consignment. No items have been withdrawn to date.”

In addition, the seven-bedroom, 6,000-square-foot oceanfront manse on Meadow Lane in Southampton that Phyllis Pressman owned is also up for sale for $38.5 million. That asking price was slashed from the initial listing of $52 million in 2020. Corcoran’s Tim Davis, the property’s listed agent, had not responded Thursday to a request for comment.

Another one of Phyllis Pressman’s abodes, her former Upper East Side apartment, has been under contract for $3.95 million since February. Sotheby’s International Realty’s broker Louise Beit had not responded to a media request Thursday.  

Fox said the lawsuit “probably shouldn’t” impact the Pressman-owned property that is being sold, “as long as nobody is trying to dissipate assets improperly.”

He added that Robert Pressman’s case is “really for the benefit of the government. The False Claims Act allows a whistleblower to bring a lawsuit on behalf of the government and it really helps the government expand its resources…this law really helps the government bring in more money that it’s supposed to get which is much fairer for everybody, who follows the rules,” he said.

In the midst of this legal action, Gene Pressman will release his book “They All Came to Barneys: A Personal History of the World’s Greatest Store” in early September. The page-turner has already been optioned by Shiny Penny Productions and Five All in the Fifth Entertainment for a series with Beth Schacter on board as its writer and Joe Wright serving as its director, as reported by Deadline earlier this week.