Out in the Open

'Confronting the truth about yourself is really hard': Rediscovering a complicated youth through adult eyes

Piper Weiss was a teenager when she along with everyone else in her Upper East Side community fell victim to the charms of Gary Wilensky, her tennis coach who would soon turn out to be a child predator.

Piper Weiss felt understood by her tennis coach Gary Wilensky, until he was unmasked as a child predator

Piper Weiss describes her childhood friendship with her tennis coach Gary Wilensky, who was later revealed to be a child predator, in her memoir You All Grow Up and Leave Me. (Submitted by Piper Weiss)
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Growing up, Piper Weiss felt different from the other girls at her school.

She didn't come from as privileged a family as some of the other students at Brearley, an elite all-girls private school in New York, that includes alumnae like Ivanka Trump and Jackie Kennedy.

"I think there's an idea that I kind of snuck in through the back door. I wasn't like a legacy of any sort. My parents were from Queens, and were children of immigrants themselves," she told Out in the Open host Piya Chattopadhyay. 

For Weiss, being herself at school was hard. She said the stakes were high to fit in because her family had worked hard to get her a spot. 

To cope, she did what she could to fit in. She would spend hours getting ready each day, putting on what she called a "costume" to look like the other girls at school, "painting" her face with makeup, stuffing her bra, and straightening her curly hair. Weiss even resorted to cheating to try fitting in academically. 

Piper Weiss at age 13, one year before her first tennis lessons with Wilensky. (Submitted by Piper Weiss)

"We were supposed to be groomed into young ladies and I just never felt like I would ever be a young lady. Good girls, you know. There was always something that felt kind of dark inside of me."

She felt alienated, and like an impostor in her own life.

In her tennis coach, a sense of solace and connection

But there was one person who made her life at school manageable — her tennis coach Gary Wilensky, who she would soon learn had a terrible secret that would shake the Upper East Side community. 

At the time, everything about Wilensky (who called himself "Grandpa Gary") seemed harmless to Weiss.

"He was incredibly charismatic and almost clown-like. He wore, you know, goofy Marx Brothers glasses. Sometimes he was known for teaching tennis on roller skates, sometimes wearing a tutu."

Weiss said Wilensky eventually became more than her coach.

"He became, in my mind, very quickly, one of the few adults who got me. I felt special. I could be like [the] ugly version of myself around him and he thought it was funny."

A Valentine's Day card from Wilensky to Weiss, postmarked February 1993. (Submitted by Piper Weiss)

Car rides with Wilensky became an escape from the pressures of school for Weiss.

He would drive her to tennis matches and sometimes stop for candy or take her to dinner. Wilensky's car was a sanctuary.

"I could say what I really thought. I could talk about my strange obsessions. You know, at the time it was with Jim Morrison of The Doors. I could be more of a tomboy. I could be me. I could just be myself and. And he got it."

Weiss said she enjoyed the attention of being one of "Gary's Girls," as he sometimes called his students.

Coach's secret identity revealed

Then, Weiss' world took a big turn. Wilensky turned out to be an imposter himself.

It was discovered that he had a history of stalking children. He'd been arrested and ordered to have psychological treatment. But according to the law at the time, his record was eventually wiped clean.

That's what allowed him to once again begin working with children — namely his young female tennis students, including Weiss.

He would become so obsessed with one particular 17-year-old student, that in April 1993 he tried to abduct her with an electric cattle prod.

A photograph published in New York Magazine's May 1993 issue of a sex doll found in Gary Wilensky's Adirondack cabin, dubbed a 'chamber of horrors' in the press. (Submitted by Piper Weiss)

The teen's mother helped fight off the attacker. Police then found 56-year-old Wilensky in his car, where he killed himself with a shotgun.

Police later discovered Wilensky had a secluded cabin in the woods located near Albany in New York, outfitted with motion detectors, night vision glasses, stun guns, and bondage paraphernalia like whips and handcuffs.

'I started to let her write her story and how she felt at the time'

Weiss was 14 years old when she found out the man she thought was her friend was dead.

"I felt for him when he died. I wondered if I was going to kill myself, not because of him, but because I was also depressed. That stuck with me more than the attempted kidnapping. And it scared me."

For Weiss, realizing Wilensky's secret identity made her question everything. 

"I wondered: if I was like him, how similar were we? And that's a really scary thought."

Weiss' mother's faint pencil marks around a section of an article in which her daughter was an off-the-record source. Weiss had kept the article with several others for nearly 20 years in a folder in her desk marked 'Gary Wilensky.' (Submitted by Piper Weiss)

It wasn't until Weiss grew older that she felt able to confront her feelings about Wilensky, in the memoir You All Grow Up and Leave Me. Its title is a reference to something Wilensky would often say to the girls he trained.

"It's cliche to say, but it was cathartic because the girl inside of me at 14 that I hated so much, I started to let her write her story and how she felt at the time."

For Weiss, learning how manipulative child predators can be helped her understand how she became so vulnerable to Wilensky's charms, and how far-reaching the effects can be.

At the same time, sharing her story surfaced new feelings of being an imposter in her.

"I still question, did I do a book right? Did I tell the truth enough? Did I make a mistake? Am I really a writer? ... Do I have any right to write down this story? I was not his victim, so this did not directly happen to me. Am I an impostor trying to be some kind of victim of trauma that I wasn't?"

But Weiss said those feelings have been relieved by hearing from some of her former classmates, who've read her story and identified with it.

"[They've] told me that they were really moved by the book and that I did represent our past, but also that they felt like impostors at the time too, and that my experience was very similar to what their experience was. We just didn't talk about it at the time. It wasn't appropriate to show your cards. And perhaps if we had, we wouldn't have all felt like such impostors and struggled so much."


This story originally aired on June 17, 2018. It appears in the Out in the Open episode "Impostors".