Male Model Says Lovelorn Socialite Hired Detectives to Destroy Him

Photo Illustration by Luis G. Rendon/The Daily Beast/Instagram
Photo Illustration by Luis G. Rendon/The Daily Beast/Instagram

In March 2021, male model Trevor Dutch Shapiro was climbing the steps to his New York City apartment when a stranger approached him with a folder and announced: “This is for you from the people in Italy.”

Inside the folder, Shapiro says he found photographs of a female friend with her then-boyfriend, who was apparently misidentified as Shapiro. The package also contained a list of Shapiro’s relatives, and personal information, including Shapiro’s Social Security number.

Moments later, Shapiro’s former lover Trudy Jacobson—a Kansas trucker-turned-Manhattan socialite who once said she likes to play piano in the nude—texted him. The couple had broken up months earlier, after a roughly three-year relationship that allegedly included exotic travel and a Rolex watch gifted by the multi-millionairess. Jacobson said a mystery man had also delivered a folder to her containing “graphic photos” of Shapiro with other women.

“I’m devastated!" Jacobson told Shapiro in a text message seen by The Daily Beast. “You are a pathological liar. Why???? We are done.”

Shapiro had previously confronted Jacobson, 71, about her nasty jealous streak, and she had admitted to spying on him before, according to a screenshot of an Instagram message reviewed by The Daily Beast. But when he asked Jacobson if she had anything to do with the folder-carrying man, she refused to answer and blocked Shapiro’s number.

What Shapiro, 34, didn’t know at the time was that the folder was just the first salvo in an alleged $1.8 million plot to destroy him.

Trucking maven Trudy Jacobson

Trucking maven Trudy Jacobson

Photo Illustration by Luis G. Rendon/The Daily Beast/Instagram

The “malicious” campaign was carried out by a group of private investigators who Shapiro claims stalked him and his associates, and savagely defamed him online and in real life, successfully deep-sixing his job prospects, according to court papers he filed in Manhattan Supreme Court. He was the subject of at least three inflammatory articles placed on a “Breitbart-like” news site, Law Enforcement Today (LET), which has been described as a morass of far-right conspiracy theories and fascist-adjacent content.

According to the court filings, Shapiro endured a year of surveillance and harassment so intense, he “required the assistance of a psychotherapist.”

Shapiro, who once appeared on an episode of Bravo reality show Project Runway, initially filed suit against LET and its executive director and spokesman Kyle S. Reyes last September. His latest accusations come in a proposed amended complaint filed March 10 that adds Jacobson and a group of private eyes as defendants and alleges defamation, tortious interference with business relations, and intentional infliction of emotional distress.

The court filings in Shapiro’s case read like a psychological thriller, and feature a supporting cast that includes a globetrotting Manhattan nurse and an Instagram influencer who, according to Shapiro’s complaint, blames Jacobson for sabotaging a male escort service she tried to launch with Shapiro. (The influencer previously made headlines as a onetime female semi-pro football player who bared her breasts in public.) Another friend of Shapiro allegedly saw her marriage ruined as a result of the smear campaign. A fourth person who was tangentially involved told The Daily Beast that her brush with the situation has been nothing short of “a nightmare.” In one court exhibit, Shapiro said Jacobson paid investigators to track people as far away as Philadelphia and Florida, some of whom she had never even met.

Reached by phone, Jacobson declined to comment but said of Shapiro and the lawsuit, “It’s nonsense. He’s an opportunist trying to cash in on a private situation.”

Jacobson’s lawyer, Alexander R. Klein, told The Daily Beast in an email that Shapiro will regret trying to add Jacobson to his litigation.

“The plaintiff is asking the court for permission to change his complaint,” Klein said. “Whatever the merits were of his first version, he was wise to not include some of the new parties and claims he is trying to add now. We expect that the plaintiff will learn that lesson the hard way.”

Shapiro’s attorney, former federal prosecutor Kenneth McCallion, declined to comment.

Jacobson, who remains married to her husband of 40-plus years back in Leawood, Kansas, fell hard for Shapiro when he was an employee of the male escort service Cowboys 4 Angels, according to an acquaintance who knows them both. And although Shapiro, in his lawsuit, describes his relationship with Jacobson as a “romantic” one, The Daily Beast located his photograph under the pseudonym “Daniel” on the Cowboys 4 Angels website, which says the company specializes in “straight elite male companions for women” and provides “the perfect boyfriend experience with no strings attached.”

In a recorded conversation reviewed by The Daily Beast, Shapiro and Jacobson can also be heard discussing payment and Shapiro’s work for the service, while referring by name to the owner of Cowboys 4 Angels. (Cowboys 4 Angels declined to comment, saying they cannot confirm the employment of anyone in their stable for privacy reasons.)

“She’s Fatal Attraction over this young male model,” the acquaintance told The Daily Beast. “But can you blame her? She really thought he loved her.”

According to Shapiro’s lawsuit, Jacobson entered his life in 2018, not long after she moved to the Big Apple to “find herself.”

The trucking maven grew up modestly in Lamar, Missouri, where her mother worked as a nurse and her father was in manufacturing. In 1987, Jacobson and her husband founded TransAm Trucking, growing it into a company with thousands of trailers serving nearly 40 U.S. states and by some accounts, more than $300 million in annual revenues.

Jacobson’s Manhattan debut was celebrated with a profile in the New York Post, when she had the upper half of her right arm tattooed with a depiction of the Buddhist deity Tara, the goddess of mercy and the female counterpart to a bodhisattva.

The socialite, who is TransAm’s chairperson, moved into an $11.5 million penthouse at the Plaza Hotel, complete with a meditation room featuring erotic paintings by an artist named Sugar Titties, and hired an image consultant to overhaul her look. Jacobson told the Post she was exploring the “sexy part” of her personality, which she had previously downplayed. This meant “a new circle of friends, including plenty of young guys who enjoy her company,” the Post profile said. Old-money New York society types tended to “scoff at” Jacobson, journalist George Wayne told the Post. However, Wayne said, Jacobson was “inventing the mold of what it means to be a modern socialite.”

Of her husband back in Kansas, Jacobson said: “We’ve respected each other’s independence since I moved.”

Court papers allege that when Jacobson met Shapiro, she lavished on him fancy trips, extravagant meals, and Chanel sunglasses, and he kept Jacobson happy in other ways—until about December 2020, when their relationship had run its course.

But, according to Shapiro, Jacobson was unable to let him go.

She allegedly hired private investigators to trail him and his friends and even hang posters around their neighborhoods suggesting they were involved in human trafficking. Jacobson also is accused of funding a series of “defamatory” articles about Shapiro, not only on LET but on and the site Ripoff Report.

In 2021, Shapiro attended a Brooklyn Nets game with a fashion editor and allegedly confided in him about tensions with Jacobson. The men joined media types in a private suite that night and Shapiro mingled with representatives of different publications for potential modeling gigs.

The editor told The Daily Beast that they shared a town car back to Manhattan, and Shapiro declined to have the driver drop him off at his Harlem apartment. When the editor asked why, Shapiro allegedly said, “I’m being followed.”

Shapiro exited the vehicle when the editor reached his stop and they chatted in the street. The fashion editor says the model then spilled stories about Jacobson that “put a fear in me.”

34-year-old male model Trevor Dutch Shapiro

Male model Trevor Dutch Shapiro

Photo Illustration by Luis G. Rendon/The Daily Beast/Instagram

“He told me that they had some affair, and she became obsessed,” said the editor, who asked not to be named in order to preserve his professional relationships. “And I was like, ‘Why would this professional woman become obsessed?’ And his response to me was, ‘Because I’m good, because I’m that good.’”

He remembers wondering if Shapiro “was a little weird” and just “being paranoid,” but he became nervous himself, bolting the door to his hotel room that night.

“It sounded like something out of a James Bond movie, like someone's following him and she's recording his conversations and his girlfriend was threatened,” the editor added. “That set alarms for me. I said, ‘Who the heck is this guy?’”

“I was just a little taken aback,” he said. “I was like, ‘Holy crap. Am I safe right now? Is this person following me?’”

Shapiro’s lawsuit accuses Jacobson of conspiring with LET and Reyes to portray him “as a prostitute, thief, perpetrator of assault, and general criminal.”

Among the other co-defendants are Reyes’ firm, The Silent Partner Marketing, which is currently plugging Jacobson’s web series on female entrepreneurs; Stephen Komorek, a self-proclaimed “counter-human trafficking expert” and security professional with ties to Reyes and LET; Conflict International, an intelligence and surveillance agency with offices in New York and London; and Jason Cohen, a retired NYPD detective and private investigator who’s reportedly worked with Komorek on “many cases.”

Reyes publicly rails against so-called woke-ism, puts job seekers through a “snowflake test” and claims not to hire liberals, does publicity for LET. Last year, he posted a photo on Facebook from Donald Trump’s Mar-a-Lago club, where he was attending a screening of Dinesh D’Souza’s election-denying conspiracy fever dream 2,000 Mules. In a court declaration, Reyes said LET gave him the honorary titles of executive director and national spokesman “for my pro bono efforts interviewing families of fallen and wounded officers” and that he does work for LET through his company The Silent Partner Marketing.

“Political correctness be damned,” the Silent Partner website tells prospective clients. “We are who we are and have what we have because of a greater good.”

None returned messages seeking comment, save for Komorek who said, “I vigorously deny the malicious and false allegations made by Mr. Shapiro. On the advice of counsel any further inquires [sic] should be directed to my attorney of record. Please do not contact me directly.”

The complaint details how the parties allegedly conspired to make Shapiro’s life a living hell.

Two weeks after he received the mysterious folder, the model was dining out with friends when Jacobson sent him a message that she apparently meant for her sleuths: “His [Shapiro’s] guy friend the one I sent photos of, is at a restaurant.”

One of those friends returned home to Florida only to have two unidentified men accost her and her spouse with a folder and familiar refrain: “This is from the people in Italy.” The lawsuit says the file contained photos of the woman at a restaurant with Shapiro which were “designed to embarrass Shapiro’s female friend in front of her husband.”

In May 2021, Shapiro was bowling with friends when he says Jacobson’s operatives shadowed him again. A worker at the Manhattan alley was apparently first to notice, handing Shapiro a note that read, “I don’t know who you are or what you do but your [sic] being watched by two cops.”

A month later, Shapiro and his friend Cheyenne Lutek launched “Him-Eros,” a now-defunct website where women could hire male companions. According to the complaint, Jacobson kept calling under a fake name and inquiring about the men. Around the same time, LET published a scathing article about Lutek and her new business, referring to Shapiro as one of her “models.” The piece also claimed Shapiro stayed at various hotels with women, attributing the information to “surveillance provided to Law Enforcement Today by Interpol sources in Italy.” (Shapiro denies visiting different hotels with women and claims no such surveillance footage exists.)

In one court filing seeking to dismiss the case, David Galluzzo, an attorney for LET and Reyes, stated, “There is nothing defamatory in those Articles. They were written by third-party contributors and address matters of public concern—the decriminalization of prostitution and the harmful effect of toxic social media influencers—and express political viewpoints and opinion that are protected First Amendment speech.”

The surveillance of Shapiro and his friends didn’t end there.

Trevor Dutch Shapiro says he and his friends received ominous notes.

Trevor Dutch Shapiro says he and his friends received ominous notes.

Photo Illustration by Luis G. Rendon/The Daily Beast/Supplied

Shapiro’s complaint says that on July 4, 2021, Shapiro and his girlfriend noticed that a man with an American flag tattoo on his forearm had followed them from Brooklyn to a bar in lower Manhattan. When they left and went to a Marshall’s store, the tattooed man pursued them. Shapiro approached the man and complimented his ink, saying he knew a tattoo artist with well-known clients including Trudy Jacobson. The man then fled the store.

One of the socialite’s PIs also allegedly pursued Lutek that same month. Lutek received a call from a Newark Airport agent who said that “her boyfriend was at the terminal waiting for her,” the complaint states. Lutek told the agent that the man couldn’t have been her beau; her boyfriend was in Los Angeles. The lawsuit alleges that the man, later identified as private eye Jason Cohen, was detained at the airport.

Cohen, Shapiro claims, was also the mystery man who handed him the folder months prior.

Meanwhile, “troll” accounts began appearing on Instagram, which warned people to “stay away” from Shapiro, and that he was “dangerous.” One linked to a LET article and used an image depicting Shapiro as a rat, and the exact same photo appeared on Jacobson’s personal Instagram account with the caption “remember him,” the complaint says.

In November 2021, the filing continues, Lutek’s and Shapiro’s parents received packages with photos and derogatory articles about them both.

That same month Shapiro’s girlfriend, a New York nurse, returned home from her hospital night shift to find someone had pinned a 6-foot-tall banner of posters outside her apartment. They bore images of her and Shapiro with the words “REPORT HUMAN TRAFFICKING” and a hotline number, the complaint alleges.

Someone posted identical flyers on telephone poles throughout her neighborhood in December 2021, apparently mapping her route from her apartment to the subway. “Although she took down the posters she saw, new ones would be posted the following day,” the filing states.

Similar posters started cropping up outside Shapiro’s apartment in January 2022.

That’s when he contacted Jacobson’s husband in a desperate plea for help.

“My name is Trevor Shapiro,” the Jan. 19, 2022 email began. “I’m sorry to write to you like this but it is time for me to reach out, since you are my last resort here.”

The much-younger model then detailed his alleged affair with Jacobson. The anguished correspondence, in which Shapiro poured his heart out in a curious attempt to end the alleged harassment, was submitted by his attorney as evidence on the public docket.

In it, Shapiro called Jacobson an “amazing woman” with a “great sense of humor.” He added, “She helped me financially, which was a huge blessing, and we traveled to places I could only have dreamt about if it wasn't for her. I will be forever grateful for her.”

Shapiro claimed that their relationship, however, eventually “became rocky” and that “the majority of our fights were about her feeling a need to have control over me.” According to Shapiro, Jacobson “was having trust issues over friends that I was spending time with.”

At various times during their love affair, Shapiro said he found private eyes stalking him. “Trudy has admitted to having me followed and photographed,” the model wrote. Shapiro referred to the folder of photographs, which he said included one of him with his high-school friend “Sally.” The rest were of Sally and her then-boyfriend.

Someone papered fliers with Trevor Dutch Shapiro’s picture all over a neighborhood, indicating he was part of a trafficking scheme.
Photo Illustration by Luis G. Rendon/The Daily Beast/Supplied

Sally, according to Shapiro’s email, confronted Jacobson online and asked, “Why are you following my boyfriend and I?” Shapiro added, “Trudy denied any of these allegations saying she didn’t have us followed this time and that someone else was out to get me.”

As for Shapiro’s Florida friend who also received a folder, Shapiro said her “entire neighborhood” received copies of the LET articles, which identified her, and that she “was destroyed and humiliated about the fake articles and wondered who could have placed them in every mailbox on her block.”

“Her husband has filed for divorce following this,” the email noted. (Court records reviewed by The Daily Beast show that the man filed a divorce petition in July 2021.)

“As you can see, all of the events over the past year points to Trudy. I have no other people in my life that would care to follow me, or even have the kind of money needed to hire private investigators around the clock,” Shapiro said.

Shapiro closed with a final plea to Jacobson’s husband.

“I know you are a smart man, and am sure you can see where I am coming from,” Shapiro wrote. “I have no other choice than to reach out to you, asking for you to speak to her to put an end to this harrassment [sic] that me and my friends are having to deal with. Several police reports, even with all the evidence, have gotten us nowhere. Can you please help.”

Jacobson’s husband did not respond to The Daily Beast’s requests for comment.

Jacobson quickly hit Shapiro with a cease-and-desist letter over the email correspondence and soon after, she and her former PI firm fell out and filed a flurry of lawsuits against each other.

The socialite’s suit against Conflict International, the investigations firm she hired to track Shapiro, claims Jacobson’s “confidential information was maliciously leaked by the company” and others after she cut ties with the company and followed one of their employees, the “counter human-trafficking expert” Komorek, to his new company. (Komorek also filed a lawsuit against Conflict the same month claiming they defamed him and interfered with his business prospects after he quit. He remains Jacobson's current investigator.)

Jacobson’s lawsuit—which also names Conflict employee Andrew McLaren, a former model-actor and Marine Corps vet—alleges she was in the market for a private investigator and learned about Conflict on the recommendation of her then-publicist Victoria Pressly. She took a liking to McLaren and Komorek and the parties inked a $1.8 million contract in March 2021. But a year later, Komorek fell out with Conflict and left to start his own investigations firm, taking Jacobson along as a client. Before leaving Conflict, Jacobson’s lawsuit claims, McLaren tried to get a referral fee from her—which she refused to pay—and divulged that they “were aware of certain details” of her confidential investigation.

This month, Conflict hit back at Komorek, who shares an attorney with Jacobson, with its own lawsuit. It claims that Komorek had displayed “increasingly erratic behavior”—which allegedly included bashing the company’s longtime CPA with comments such as, “this guy may be a Jew but he doesn’t know his ass from a fucking hole in the ground”—and that he flashed “numerous firearms and weapons to Conflict employees present on the weekly video meetings.” The lawsuit also says Conflict learned that Komorek was not an ex-Delta Force, CIA, and FBI hostage rescue team member, as he claimed, but that instead he’d previously worked as an IT professional and a chaplain’s assistant in the National Guard.

In Jacobson’s investigation, the lawsuit alleges, Komorek proposed disclosing confidential information to third parties without authorization from Conflict or Jacobson. When Komorek’s bosses expressed concern that his plan could compromise the case, Komorek allegedly replied in part: “If you are not confident in me my ability to provide a sound and safe strategy for the client, replace me; This is one small piece to a larger puzzle of getting criminals in jail.”

Trudy Jacobson allegedly hired private detectives to follow her former lover.

Trudy Jacobson allegedly hired private detectives to follow her former lover.

Photo Illustration by Luis G. Rendon/The Daily Beast/Instagram

The lawsuit says Komorek’s responses “were not rational or reasonable.”

“Conflict, as private investigators, simply investigate and report facts to their clients,” the filing states. “Conflict does not ‘put criminals in jail.’”

Komorek, the lawsuit continues, also convinced Conflict to retain and pay Reyes and Silent Partner Marketing tens of thousands of dollars for publicity services. As a result, LET published several laudatory stories about Conflict from 2019 to 2021. According to the suit, Komorek claimed he had “complete editorial control of what would be published on LET.” Conflict also claims it “had no prior notice that LET had published” articles targeting Shapiro and even suggests Komorek forged a memo submitted as evidence that indicates Conflict provided LET with information.

After Komorek’s departure from Conflict, LET soon began posting “slanderous” items about the company and its associates, written by a pseudonymous contributor named “Sgt. A. Merica.” But Conflict says in its lawsuit that Komorek is likely the author: “Several factual items within the story are only known to Conflict and Komorek.”

McLaren messaged Jacobson and claimed Komorek failed to pay him a 10 percent commission from taking her on as a client, according to Komorek’s suit.

“Sometimes it takes years and some soul searching to realize who is lying and who is telling the truth,” McLaren wrote. “I wish you success and happiness and I have faith you will eventually figure out who is lying and who is telling the truth.”

On March 14, Conflict asked a federal judge to issue a restraining order prohibiting Komorek from revealing confidential information protected under a non-disclosure agreement he signed, arguing the “Sgt. A. Merica” articles in LET were a violation of his NDA.

When Jacobson, the self-styled “Lady Trucker,” graced the October 2018 cover of the “aspirational luxury lifestyle” magazine Resident, she shared one of her life's biggest lessons. “Always be authentic, be who you are no matter what,” Jacobson said. “You can’t be as happy as you can be by living behind a mask if you are living a life that is not suitable to you. Be willing to take that risk at any age.”

Her move to Manhattan, she said, was a mutual decision with her husband. “Our friends say that they have not seen either one of us as happy as we are now,” she told the outlet.

In 2022, Jacobson worked to reinvent herself again, this time launching a short-lived talent agency with Pressly and issuing press releases announcing a novel titled Diesel Smoke and Dangerous Curves. It’s unclear if the book was ever published.

They also commissioned a song called “Mother of Liberation.” Written and performed by English-born singer Davey La, the lyrics describe Jacobson as a model of by-your-bootstraps female empowerment: “She’s got balls and she’s got class, cuz she’s a badass mother. Mother of liberation. A mother trucker.”

But the women’s relationship disintegrated by the end of the year. “I am no longer associated with Victoria Talbot Pressly,” Jacobson commented on one of Pressly’s tweets. “Please remove all posts by you per my trademark regulations.”

Pressly declined to comment.

After ditching Pressly, Jacobson hired Reyes’ marketing firm to promote Great American Women, her web series on “ambitious female philanthropists and entrepreneurs.”

While that show releases new episodes, the legal battles over Jacobson’s alleged harassment of Shapiro rage on.

One person acquainted with Jacobson and Shapiro told The Daily Beast that the socialite “made him dependent on her” and essentially became his employer.

Still, they emphasized the exhaustion of being caught in the middle of the ex-couple’s drama.

“All you want is money, Trevor, and Trudy, all you want is revenge,” they said. “Leave me out of this.”

“If you’re walking into a courtroom, the truth comes out.”

Read more at The Daily Beast.

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