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Max Winter · Dec 23, 2025

the ghost of uncle cy

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Max Winter · Max Winter

Black sheep. Convertibles Flying off Cliffs.

The account started as an experiment in July. My theory was that it could be a home for my short stories that have sold for film, but had no traction with traditional publishers.

Turns out, it was much more. I’ve gotten to know people from all over the world who choose writing as an important part of their lives — not for subscriber money or movie deals — but to share something human that resonates with someone out there.

Thank you for the hundreds of comments that blew my mind. Incisive takes that I never considered consciously while writing.

Hope you enjoy this final post of 2025 and you’ll stick with me into 2026 and beyond. Excited to see what’s next…

In the meantime, a wild family tale…

So, the story goes like this:

Uncle Cy and his third wife get drunk at a party.

They’re driving home in the Hollywood Hills.

Some people say they’re in a Thunderbird. Others say it’s a Mustang.

But either way, it’s definitely a convertible — we’re talking about Uncle Cy here.

Regardless: they go flying off a cliff.

They think they’re gonna die.

In midair, Uncle Cy turns to his third wife and says:

“Pretty good view, isn’t it?”

They wake up the next day in Cedars Sinai covered in bandages. Both live to tell the story.

Now it’s family lore.

Cy’s a legend.

But there are only a few people left who remember him at all.

Seymour “Cy” Pollock was my great grandfather’s much younger brother. I probably met him when I was a kid, but I don’t remember. Instead, I know him from stories and pictures.

The perpetually dark tan.

The thick, white masses of hair.

The perfect white teeth — probably capped.

The tight, white shirt with huge 70s collar, unbuttoned basically to his belly button.

The gold chain.

The tight, white bell bottoms.

White patent leather shoes.

“He looked like Elvis Senior,” my Aunt Jo says.

(Or maybe a Jewish Uncle Baby Billy from Righteous Gemstones.)

Sy was the Black Sheep.

The youngest mistake child in a large family of talented people who are all gone now. There was Aunt Dot, an opera singer who studied in Italy. Aunt Emma, who was supposed to be a concert pianist, but got arthritis and became an artist instead. Their father died young, and Cy didn’t get along with his mother, so he ran away to Miami as a teenager.

Funny: I’m obsessed with people who ran away to Miami as a teenager.

In the heyday of Miami in the fifties, Cy became a hotel cabana boy — fetching pool towels for wealthy vacationers. He was incredibly handsome and charming. So, naturally he ended up marrying a much older oil heiress when he was only seventeen.

The first marriage didn’t last long. The story goes that once Cy started itching to leave her, the woman was so distraught she told him:

“At least take an oil well!”

Offered to give him an oil well in the divorce settlement!

But apparently the principled Cy turned down the well and arrived in Los Angeles with nothing, one of the youngest divorcés imaginable.

The family thinks it was the next wife that Cy had his children with, although nobody’s sure.

It’s hard to keep track.

At some point he had a son and daughter — probably with “The Cat Lady.” Nobody can remember her name. All they remember? She had nine cats.

Cy had very delicate, sensitive hands. His hands were so delicate, in fact, that for a lot of his life he made his income from his ability to hand-make lug nuts that went on Lockheed Martin airplane wheels. He owned a tool and die company called Idee Odee Inc. in some industrial wasteland in Glendale, California. The only record of the company when you look it up today is that at some point that area of Glendale was put through an environmental review and forced into a government clean up.

During the peak of Idee Odee, Cy met and married his third wife, Jodi Turner, a Mormon escapee in Los Angeles, thirty years his junior.

“She was a tall drink of water!” my Aunt Jo says.

It was the sixties by now. They lived in a three floor, split-level house in the Hills.

My cousin Henry jumps in with a story from that era:

Cy was at his house in Hollywood Hills one day and he heard the bell ring. He went to the door and it was a young woman who said she was doing a survey on people who use Vaseline “in the bedroom.”

Cy told the woman:

“Yeah, my wife and I use it!”

The woman was relieved. She said everyone had been shrugging her off. Too shy. So, it was nice to meet someone who was honest about it. Could she ask how Sy and his wife used it?

“Sure,” he said. “We put it on the doorknob while we’re having sex to keep the kids out!”

Henry was ten-years-old when Uncle Cy told him that story.

Around that time, he sent Henry a bath robe from Caesar’s Palace in Las Vegas as a birthday present.

(Probably stolen.)

At some point in the sixties, my grandmother moved my Dad and my Aunt Jo to Los Angeles and got re-married to a very wealthy Beverly Hills man named Milton. (He was supposedly insane and ended up dying in a mental institution, but that’s another story.)

Jo got to know Sy when, as a twelve year-old-girl, she was arrested for raiding her parents’ medicine cabinet for barbiturates. When some girl in her class passed out, they dragged little Jo down to the police station. Since her parents were out of town, Cy was the only “adult” around to bail her out. Jo ended up staying with Cy and Jodi and loved both of them.

Of course she did!

When she turned thirteen, Uncle Cy thought it appropriate to gift her some white Go Go Boots.

Cy and the crazy stepdad Milton loved gambling. They’d take the kids down to Tijuana to the horse races at Agua Caliente. (This is fascinating to me. Gambling was illegal in California. So, the place to take a leisurely day trip to bet on horses? Across the Mexican border. Talk about more innocent times…)

Cy also took a liking to my father, who he brought to the Fireside Lounge in Encino, a sort of bar/gentleman’s club where I’m sure they got into all kinds of shenanigans, even though my Dad was underage. My Dad started playing the drums at Fireside around that time, and would roll Milton’s Bentley down the hill to sneak out for the night to see James Brown at some Downtown LA club.

He also started wearing Nehru jackets and being an overall weirdo.

My Dad’s biological father back in Jersey, a more traditional real estate guy, who I remember had plaques in foyer that named him “Jew of the Year,” openly feared that my Dad was “becoming The Next Cy.”

Of course, in many ways, my Dad *did* become The Next Cy.

And as my Aunt Jo points out today: “There’s a little bit of Cy in you as well.”

But more on that later.

At some point, the Mexican guys that Cy had working for him at Idee Odee Inc. took over the business and cut him out. And after almost ten years, his “tall drink of water” Mormon wife got tired of dealing with his hijinx, left him, and moved to New York.

It was the beginning of a long downfall for Cy.

By the late seventies at my parents’ wedding in Beverly Hills, there were plenty of models for the aging bachelor Cy to flirt with — including Jerry Hall. But infamously, he left the wedding with the housekeeper’s daughter. (Age unknown.)

There were a series of waitresses and similar types after that. Cy would always show up with some random younger paramour or another. When he lost his Hollywood Hills house, he decamped to Burbank. By the time he was in his 60s and early 70s, he moved in with a waitress that my Aunt Jo describes as “not a romantic relationship.” Actually, sounds like Cy helped a struggling single mother raise her two kids in exchange for room and board.

By the very end, Cy was living somewhere off the Vegas strip, taking a public bus to the casinos. He had emphysema from a lifetime of cigarette and cigar smoke, and carried an oxygen tank with him. After his son Jeff died of cancer, the final woman to take Cy in? Jeff’s widow — a Vegas showgirl named “Angel.”

Sy died around the year 2000 in Vegas. His daughter was so embittered by him, his treatment of her, and his life choices that she did absolutely nothing in the wake of his death. There was no funeral. The only memorial of his life is a small rock that my artist Aunt Jo painted with his name on it and placed near the grave of my great grandmother and her husband. (Cy’s brother.)

I knew my great grandmother Cele Pollock as “Nano,” but I didn’t know her well. My best memory of her was that as kids growing up in New York, we were forced to speak to our “Nano in California” on the phone every Thanksgiving.

Every single time I’d ask her: “How you doin’?” here’s what she’d say:

“I’m horrible!

Every. Single. Time.

“HORRIBLE!

Every year.

The woman didn’t hold back.

(I had to hand it to her for telling the truth at least!)

She’d yell: “I’m HOORRRIBLE!!!!!

Then I’d pass the phone to my little brother and she’d tell him the same damn thing.

What a family tradition.

We came to expect it. Try hard not to laugh.

“Nano” didn’t particularly care for Cy. She was an interior designer that lived in Beverly Hills and whenever someone she cared for was coming to her house, she’d spiff everything up and take out her good china on the main dining table.

(In fact, I inherited some of her gold-plated china.)

But when Cy came?

They’d eat in the kitchen on paper plates.

It was that kind of relationship.

And yet, Uncle Cy’s “final resting place” is next to Nano.

Cy and Nano are my only two relatives who died on the West Coast.

After thirteen years of living here, I’m likely to be the third.

Even though I’m a born-and-raised New Yorker who strongly identifies as a New Yorker, over the years I’ve become fascinated by my family’s history and ties to Los Angeles.

When I first bought my condo behind the Whisky a Go Go on the Sunset Strip, my Mom took me out in front of the building and pointed around. Just a few blocks to the right, past Greystone Mansion, is where my parents got married (and Sy ran away with the maid’s daughter.) Just one block up ahead, on Doheny, was my father’s first apartment, where he was living when he met my Mom. Then just two blocks to the left, above Sunset Plaza, is where Nano lived and died.

Somehow, unbeknownst to me as a newbie in L.A. who knew nothing about the geography, with a choice of anywhere to live in the largest county in the USA, I’d bought a condo dead center in the vortex of my family’s history in the city.

For the record, we did have a ghost in that Sunset Strip condo. Haunted the guest room. Sure, it could have been a hair metal rocker who caught a heart attack after doing too much blow off a stripper’s ass in 1983. (There were a lot of those guys around. The infamous Mötley Crüe house is across the street.)

But it could also be Cy.

Lately, for some reason, Uncle Cy has been on my mind.

Even my dreams.

My grandfather was right to fear that my Dad was “The Next Cy.” He ran away to Vegas at age seventeen with an older woman (apparently named Roberta — I never knew this story until very recently.) His crazy rich stepfather Milton (the guy who ended up in the looney bin) took it upon himself to go to Vegas and bring him back at gun point.

My father lived a wild life that I talk a bit about here, and there’s this story that I once sold to Paramount as a movie. After Roberta and my Mom, who were both older, he had a series of younger girlfriends half his age. He lived in the Chelsea Hotel for over 20 years, which I wrote about here. He always said they’d have to take him out of the Chelsea “in a box” — and that’s basically what happened. He died broke and in a relationship with a woman my age (that he called “Baby.”)

Here’s the thing: the Jews, artists, and weirdos in my family (pretty much a Venn Diagram overlap) feel like my real family. And maybe I’ve become obsessed with Cy because I’ve already become The Next, Next Sy.

I’m already the Black Sheep of my family for many reasons. After 45 years of bachelorhood and many bad relationships, I recently married a woman 16 years my junior — in Las Vegas, with Elvis as our officiant. My wife is a tall drink of water. Born on a farm in a town of 25 people. She’s not Mormon… but close enough.

My Aunt Jo says that Cy was able to marry an oil heiress and get through life the way he did because he was funny and charming. The traditional members of the family didn’t think much of him, but the artists like my aunt and grandmother couldn’t resist him.

Sometimes, my wife talks about a glint that I get in my eye, or a slight curl of the lip, a sly smile that comes over me. Sometimes she says, I look like a mischievous seventeen-year-old boy. The look of someone who gets away with things. For some people, this inspires rage. Others find it difficult to resist.

It’s hard not to think in those moments: there’s a little bit of Uncle Cy’s blood flowing through my veins.

(Hate to break it to my wife, but our kids are gonna have a little bit of that blood flowing through them too… but only a little bit…)

Anyway, I think it sucks that Cy didn’t get a burial. Or a funeral.

He got a painted rock.

He won’t be remembered.

As sad, lonely, and painful some of Cy’s life clearly was?

It also sounds fucking amazing.

Full of thousands of stories that I only have a tiny hint about. Honestly, that’s the kind of life I’ve always wanted.

(To be clear: not the string of divorces, embittered children — or dying alone with only my son’s showgirl widow by my bedside. My plan is one loving marriage to last a limited remaining lifetime and a found family that doesn’t abandon me.)

But like Cy, a life full of stories.

A life lived with audacity.

Around when I was seventeen, I once stood up on a Metro North train in Westchester and drunkenly yelled at all the commuters: “I’ll never be you people!”

At the core of my soul, I’d much rather be a guy whose convertible Firebird is flying off a cliff and who turns to his beautiful young wife and says:

“Hey, at least it’s a great view.”

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