In the gritty, neon-lit streets of 1960s New York City, where crime rates were climbing and urban unrest simmered, the NYPD rolled out an audacious plan to fight back. On July 1, 1969, in Brooklyn’s 78th Precinct, a volunteer officer named William R. Winter stepped out into the early morning hours—around midnight to 1 a.m.—dressed not in the standard blues but in a miniskirt, high heels, a wig, and makeup. His mission? To pose as what a now-iconic photo caption called “a tall voluptuous broad” and lure out muggers, gropers, or worse in a high-crime pocket of Boerum Hill. This wasn’t just a stunt—it was a snapshot of a city fighting to reclaim its streets with ingenuity and nerve.
A City Under Siege
The 1960s were a wild ride for New York City. Between 1960 and 1969, murders spiked by 150%, and muggings became a nightly fear in neighborhoods like Brooklyn. Economic shifts, post-WWII migration, and social upheaval—including the Stonewall Riots just days earlier on June 28—created a tense backdrop. The NYPD, led by Commissioner Frank Leary and soon Howard Leary, faced a daunting task: restore order in a city fraying at the edges. With limited tech and resources, they turned to creative tactics, and the decoy operation was born.
Patrolman Winter, a family man with a wife and child, volunteered for the Tactical Patrol Force (TPF), a unit known for tackling tough assignments. His role was simple but bold: blend into the nightlife along Atlantic Avenue, a hotspot for street crime, and act as bait. The disguise wasn’t just for show—muggers often targeted women perceived as vulnerable, and Winter’s getup was designed to draw them out.
The Pinch and the Punch
Around 1 a.m., the plan worked. Two men approached Winter, likely sensing an easy mark. One pinched him inappropriately—a crude move that might’ve signaled a robbery or assault. But Winter was ready. In a moment that’s equal parts gritty and cinematic, he “pinched” them back—not literally, but with handcuffs. He subdued both suspects on the spot, with backup swooping in to seal the arrests. The operation was a success, and Winter wasn’t done: in just six weeks on this detail, he reportedly nabbed six predators, proving the decoy tactic’s punch.
The moment was immortalized in a black-and-white photo that’s since become a minor legend. Winter, mid-stride outside the 78th Precinct, wig slightly askew and expression all business, captures the absurdity and bravery of the assignment. The caption on the photo, printed in The New York Times morgue files, leans into the era’s cheeky tone, calling Winter’s disguise “a tall voluptuous broad” and noting his family-man status, as if to reassure readers this was all in a day’s work.
A Glimpse of Policing’s Past
This operation wasn’t a one-off. The NYPD’s decoy units, with officers posing as drunks, cabbies, or, in Winter’s case, women, were an early experiment in proactive policing. These tactics foreshadowed the more aggressive strategies of the 1970s, like the “ghost squads” under chiefs like Patrick Murphy, and even the controversial “broken windows” approach later on. The 78th Precinct itself, still standing today (and famously the exterior for Brooklyn Nine-Nine), was a microcosm of a city willing to try anything to stem the tide of crime.
The story also reflects the era’s contradictions. The caption’s playful language and the operation’s reliance on a male officer in drag highlight a time when gender norms and policing tactics were less scrutinized but no less bold. Winter’s willingness to step into high heels for public safety speaks to the NYPD’s adaptability—and the lengths officers went to in a city on the brink.
Why It Matters
This quirky tale from 1969 isn’t just a footnote in NYC’s history. It’s a window into a transformative decade when the city grappled with rising crime and laid the groundwork for its eventual recovery in the 1980s and beyond. The decoy operation, with its mix of courage, creativity, and a touch of humor, shows a police force and a city refusing to back down. It’s a reminder of New York’s resilience—whether it’s a cop in a miniskirt or a community rallying to reclaim its streets.
Want to see the photo that started it all? Search “undercover cop Brooklyn 1969” online—it’s a time capsule worth a look. And the next time you’re near Boerum Hill, imagine Patrolman Winter strutting through the night, ready to turn the tables on crime, one “pinch” at a time.
