My Subhuman Ex-Girlfriend and Her Insane 1% Clown Posse (Part II)

Legal Disclaimer: While this post mentions actual people and events, the entirety of the post is meant for entertainment purposes only. None of the following statements are to be considered factual or true. I, David Friedlander, the author, place complete intellectual and legal burden of conclusions derived from reading what I have written upon the reader. Further, none of my statements are meant or should be considered legally binding or intended as a means to communicate with any person(s); further, the fantastic, deliberately ambiguous nature of my writing precludes any of my statements, including those statements in any and all linked posts, and those statements as they relate to my children, to be used as evidence for arrest or proof of my mental fitness, lack thereof, or any other legal proceeding intended to limit my ability to freely exercise my First Amendment Rights as an American, writer, historian, researcher, seeker, and — above all else — a storyteller. I have a decade of notes showing how I use the written word to make sense of the world, hoping that inquiry has relevance for those who choose to read what I write. TLDR: I’m just telling my too-fantastic-to-be-real stories. Truth is in your Court.

There’s Something Tacky and Awful Going On In Them Hills

Be sure to read Part I first, here.

The country north of Westchester and throughout southwestern Connecticut is some of the world’s best. We drove Josslyn’s BMW wagon on quiet, perfectly-paved roads through poetic little New England towns and low, rolling mountains that are covered in life-giving trees much of the year but passed by us in seasonally-appropriate solemnity.

Arriving at dad’s place meant turning down a tiny forest road inlet with little more than a standard mailbox to indicate its existence. After one mile on the road, one pulls up to the “grounds.”

My view from the guest house the first weekend in Connecticut. 

The first thing I said upon viewing it was, “I didn’t know your dad was Lord Grantham.”

The Shapiro’s ill-got, 187-acre estate. My erstwhile Connecticut country home for a couple years.

At this point, I recall asking Josslyn what her dad did for money, trying not to be impolite, but genuinely curious. 

She confessed she was reluctant to bring me to his home because it was so gaudy and not what she was about. She said Ira had an art publishing business that he sold. Jackie was some hot-shit eighties art agent. They met and married in the eighties, made some lucrative investments together, including real estate, etc. I knew how one investment could blow up, so I didn’t pry, trusting I’d find out organically how they could end up in such a spot. 

We dropped our stuff off in the private guest house we’d use when we visited — one of four of five on the property. Our house was near the barn, beyond the courtyard separating the stables and garages from the mansion. There were peacocks and decorative horses; this “menagerie” comes with the house’s price tag (I think they dropped the price ~$20M in the few years it’s been on the market).

The private guest house I stayed in while in Connecticut — one of several.

After settling in, we headed to Sky and Chris’s place. Their home was roughly 5,000 square feet with ample grounds and a pool. Josslyn said it was one of Ira and Jackie’s investments and, much to Josslyn’s disapproval, the parents paid most of the young couple’s expenses, making the younger couple hopelessly dependent on the older ones. Two new BMWs were parked in the barn/garage which teemed with new sports equipment. I detected a tinge of envy, since Ira’s fortune were made after Josslyn was grown.

The first person I met at the packed home was patriarch, Ira, a wiry old man with a wardrobe and bearing frozen in 1995. Within moments, he revealed to me, for the first time, that Josslyn had a first husband — not Evan Rose, the father of her one son, celebrated urban planner, mortal victim of cancer…not the good marriage. 

The vainglorious Ira Shapiro in 2019, blowing his cover. 

She would later claim she forgot about her first multi-year marriage with another guy named David (there are a lot of Davids in this story). 

She met David number one at Columbia studying climate science. She explained they didn’t work out because that David, not me, was from a poor Chinese-American family and carried a big chip on his shoulder about her and her family’s wealth. She convincingly claimed she couldn’t control that her family was rich. He also gave her grief about the amount of toilet paper she uses. [David to David note: totally! Such a hypocrite.]

Ira would end up being the grand-master for this Thanksgiving parade of hyper-inflated egos and bank accounts.

There was her evil stepmom, Jackie, a neckless seventy-something who smiles to people’s face while covertly manipulating them with her cunning and leveraging family infighting and economic manipulation for personal power-grabs.

Center: Jackie is a feminist revolutionary, starring as both evil stepmom and controlling real mom. Left: clone bridesmaids. 

There’s Jackie’s protege and daughter, Sklyar, an long, lean, manipulative, and greedy former fashion industry worker turned real estate stylist…or something. 

My time with the Shapiro’s was dominated by the wedding of Sky to Chris Ivey, a profoundly stupid, haplessly-striving lapdog blowhard she met when she was a teen (her constant eye-fucking me made me think she cheated on him, frequently).

Left: Hapless striver, clickbait CEO, Chris and resource/man-eater, Skylar. They told me they eat their dogs when they get bored and buy ones that look just the same. No one notices. 

Chris and his family, especially his sad-sap dad, also at Thanksgiving, were local opportunists who ingratiated themselves with the Shapiro-Dedell clan and, I’d find out, other wealthy folk.

Chris was ex-military, ex-Harvard-correspondent-Business-night-school certificate holder and the bro-founder at a lower-Manhattan click-bait marketing firm. He drove his X5 from Connecticut into the city most days. He later traded the Bimer for a Tesla Model X, because of the environment. His six-hour daily commute — I’d find out — were signals to show mom and dad-in-law, who were entrusting them with their princess and paying most of the bills, his hustle.

My ex-girlfriend’s step-brother was crazy into penguins. He did Krav Maga for a few years, then stopped. That’s it for Gavin.

Also there was Skylar’s brother, Josslyn’s half-brother, Gavin. He was an awkward, 6’7″, late-twenties man-child there with his justifiably angry, compact, middle-class-born girlfriend, Kate. The couple lived in Astoria, Queens, where he primarily worked as a graphics contractor. But Gavin’s real passion, I’d find out, was penguins. He built a penguin-themed freemium app. Gavin would later trade Kate in for someone taller and richer, much to the delight of the family.

There was Courtney, Josslyn’s older sister from Barb and Ira’s marriage, and her fiance David Remnitz. 

Courtney (Rothstein-Shapiro) was, like most of the Shapiros, long and lean, though she was the only one I knew with a boob job. 

David was a short man with sharp facial features and an aggressive stare. His graying head of black hair sported the $100-haircut and his soft body was draped in the overpriced and banal clothes that unmistakably signaled his membership in the banker and country club class. 

Both were battle-scarred veterans of multi-million dollar divorcees. They preemptively answered quizzical looks by claiming a deep love of food as the basis of their union.  

Courtney had two two teen children that lived with her and David part-time in nearby Greenwich, Connecticut. David supposedly had twin daughters in college — they each had their own lofted rooms in Greenwich — but as far as I could tell, he had no contact with them other than paying for their private-school tuition and credit card bills.

Courtney was an executive working at a some marketing firm for big, multinational corporations. She traveled a lot. 

David was a big-contract “cyber-security expert” at Ernst & Young before going into early retirement after a botched shoulder surgery. His disability checks were tallied based on a large percent of his large, former salary, so he didn’t need to work. When I met him, David had just impulse purchased an Audi R8s online. He couldn’t drive the car because of his shoulder and all the meds he was on, including the prescribed THC/CBD cookies he gave me and Josslyn. [Thanks, David!]

One of Skylar’s besties and Chris’s sister, Taylor Ivey, hawks overpriced sweaters that act as 1-percent fashion signals, with one word graphics like “Montauk” and “Martha’s Vineyard” letting the world know where they hide. I’m assuming Ellsworth sucks, too.  

There was Chris’s sister Taylor and her abusive boyfriend, Scott, who is the heir to the U.S.’s (world’s) second largest cattle ranch REIT (real estate investment trust). Scott’s verbal ejaculations included sermons on the bogus connection between factory farming and GHG emissions — my contribution to that spooge being, “you must not read.”

Become One of US

Me bro’ing out with the groom at the “big wedding.”

Despite the tackiness and waste of this universe, that Thanksgiving weekend would be the first of many sumptuous weekends up north. 

The rest of my existence was so hard, I welcomed the break and the family’s ostensible kindness, graciousness, and downright deference.

The Shapiros, Iveys, etc. loved me.

Because I am reflexively gracious with hosts, I provided a fun house-guest and an affable access point for the judgmental Josslyn, who was the real alpha of the operation, despite her seeming quiet and modesty. She was the one no one, especially Ira, could impress with riches.

Josslyn’s classy, tall, accomplished replacement boo. 

I was also a mature, stable, worldly man-foil in a sea of provincial, of-the-moment boys. 

I didn’t feed into Ira’s inappropriate, 1980s ad-industry-era jokes. I respectfully corrected Chris’s fresh-off-the-podcast wisdom. The Shapiros fancied themselves athletes and they marveled at my athleticism, especially my numerous runs and trail races through the Connecticut hills.

By the second year of our relationship, Josslyn and I were going north two or three times a month. For all intents and purposes, I had a free country home and hosts less than two hours north of the city. 

My ex-girlfriend’s dad and step-mom’s backyard in Connecticut. It’s nice being in nature. 

I liked living in luxury, not worrying about money or the outside world. In fact, I believe everyone deserves a form of this ease in their lives, not just a few bad people….

Josslyn and I eventually broke up.

The reason, she would claim, was that I did something that made her more embarrassed than she’d ever been with a partner. 

The offense happened at a Climate Extinction Rebellion salon at Passive House pro Ken Levenson’s Park Slope townhouse. I said something to the effect of, “we know this, Ken. [basic climate science/status.] What are we going to do?” [Note to Ken: more single-family homes and combined Passive townhouses, ain’t it.]

Her declaration was happy news for me. While distracted by the relationship’s ostensible benefits, something never felt right. Her mock outrage at my comment was a perfect demonstration of our divide. My aggressive question about climate adaptation was in appropriate. Her sitting on a PhD in Environmental Sciences at the planet’s most desparate hours, spending her days doing nothing but errands and taking her kid to school, traveling and enjoying the company of her millionaire parents on the weekend was classy. 

Got it. 

And Another Thing

When Josslyn and I broke up, it was a huge relief. My body long knew something was not right. For months, I was suffering from night sweats and morning diarrhea — a bowel condition that is the literal manifestation of losing one’s shit.

Something never felt right and never looked right. She acted and dressed like the rich, middle-aged, never-party woman she is. She was tall. 

Josslyn was too staid for me. Most of this was cultural, but the anti-depressants she took did not help. In our two years together, she did not cry or orgasm once—these being outlier conditions of my past partners, and conditions I appreciate. 

I knew the Shapiros were not my kinda people

The Shapiros were from Florida and Scarsdale, and their value system seemed grounded on the former’s swamp-foundation-stable Ponzi-economics and the latter’s remote, passive exploitation of nearby and dispossessed urban populations.

And despite her education, Josslyn wasn’t not a well-rounded person. She couldn’t dance and was lost in the bedroom. She never made food without a recipe. Her PhD seemed to be used as a social and professional climbing mechanism rather than a means to an end. She had almost no understanding of art, history, or geography. Even with her Columbia PhD, she didn’t know what country Amsterdam — a paragon of climate protection — sits in.

Josslyn later told me she expected me to protest the breakup. Instead, she gave me an easy out to what amounted to a high-class rebound relationship.

My period of rebuilding was temporary — her’s was not. 

Like many who have the option to not work, she seemed content to amke every day a “personal-day.” She was okay letting her embodied talents lay fallow. She had worked in the public and private institutions and she said they didn’t care, so why try?

She believed that living a humble life, going to the coop, taking her son to Poly Prep — where she had transferred him from Blue School, right when Poly Prep was going through their blackface PR scandal — was enough. She knew her son would be okay because of her family. 

Josslyn knew she’d be okay. She had enough money coming in from her Evan’s Social Security and “an” investment home she had in San Francisco to pay for living expenses, including her mortgage and private school tuition. She received low-cost USAA health insurance because a distant uncle was a veteran. 

Her investment property — also something she was slow to tell me about — was in San Francisco. Her and her late husband Evan purchased it when they lived there. They lived there only a few months before having to return to New York City for Evan’s cancer treatment. They bought a second home in Brooklyn, around the same time I did with my ex in 2013.

I found out later, she had money coming in from an “organization [that] primarily operates in the Truck Rental, Without Drivers business / industry within the Automotive Repair, Services and Parking sector.” 

The Link

In the depths of the lockdown, I decided to see if I could find out more about the Shapiro fortune, since it was never revealed, and I had a lot of time on my hands.

There wasn’t much information online except for a defunct Ira Shapiro Architecture office in West Cornwall — and Ira wasn’t a registered architect so far as I knew — and one link. 

In the next, and probably final, installment, I’ll explain the link, and how it opened up a whole set of creepy, new possibilities. 

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