Jess Swanson, Senior Editor
Jess Swanson, Senior Editor
Jun 2020

A blur of businesspeople dart past H. Keith Melton in Manhattan’s Financial District. Dressed in a dark blazer and red tie, the 75-year-old eyes a white, six-inch-long chalk mark running horizontally across a green sidewalk barricade. “Is that just a smudge,” he asks, cocking an eyebrow, “or is that a secret signal that an operation is going to take place at 8 o’clock tonight?”

Soft-spoken and walking with a wooden cane, Melton is completely unassuming, which he’ll later demonstrate is key to espionage. Over the past four decades, he has acquired one of the largest tradecraft collections of all time, including a Nazi Enigma code machine, a WWII-era cigarette that fires .22-caliber bullets and the ice axe used to kill exiled Russian revolutionary Leon Trotsky in Mexico City. “I tend to specialize in gadgets,” he says. “My fascination has been traveling the world to obtain every example of spycraft.”

He has donated 7,000 items from his trove to the International Spy Museum in Washington, D.C., on whose board he sits. He also advises the CIA and was a consultant for the TV series The Americans, whose protagonists are Reagan-era Soviet spies living undercover in the D.C. area. Recently, Melton and retired CIA senior intelligence officer Robert Wallace co-wrote Spy Sites of New York City: A Guide to the Region’s Secret History. He’s here in Manhattan today to teach me that espionage, like magic’s sleight of hand, happens before our very eyes, undetected.

H. Keith Melton in Central Park

So, too, the greatest spy sites in our country’s history are all around us. Over the next few days, he’ll take me to dozens of public places—including a Wall Street Starbucks, a luxury Midtown hotel and even the steel globe at Columbus Circle—to explore the secret history under our noses.

I look back at the chalk mark and figure that it’s probably just a smudge. Melton doesn’t look so sure: “There’s more spying now than at any other point in history.”                                                                  

Melton and I weave between the graves at Trinity Church, stopping ten feet short of Alexander Hamilton’s pyramid-like tomb. Though Hamilton was responsible for deciphering secret letters during the Revolutionary War, we’re here to visit the less ornate gravesite of a decidedly modest spy, Hercules Mulligan, a tailor who would eavesdrop on British troops as he fitted them in his shop nearby and became a bit part in the Tony-winning Broadway musical Hamilton. Whenever Mulligan noticed the British troops ordering heavier, woolen clothing, he knew that signaled movement north, and passed the intelligence to the Revolutionaries. “This is what we call commercial cover,” Melton explains. “It’s been used throughout history, and when it’s done well, it’s impossible to detect.”

When it comes to spying, most people think of the Cold War, the Soviet Union or perhaps the fictional MI6 agent James Bond and his glamorous undercover life filled with accents, trysts and fancy cars. But after working as an intelligence officer for the CIA and serving as the director of the Office of Technical Service, the now-retired Spy Sites coauthor Robert Wallace clarifies things. “Most spy movies have far more violence and far more sex than I ever had an opportunity to do,” he says, chuckling to himself. “I never even carried a weapon.”

Real spy stories might not be as lurid as the ones Hollywood conjures, but they shape history.

Considered “America’s first spymaster” and “the founder of American intelligence,” General George Washington relied on covert information to defeat the British, one of the most powerful and experienced armies in the world at that time. He also learned the importance of keeping spies’ identities protected after 21-year-old spy Nathan Hale, who was untrained, ill-equipped and conspicuously tall, was hung by the British in 1776. “Washington understood what a good spy was not to do after suffering the consequences,” Melton says.

We walk past the skyscrapers on Wall Street to the four-story Fraunces Tavern, which claims to be the oldest surviving structure in Manhattan. It’s also where crucial Revolutionary War espionage took place. On the third floor, a glass display honors Hale, who Melton says likely met with Washington and the Sons of Liberty here, but nowhere in the temporary exhibit is he called a spy. Melton’s not surprised. “Governments look smarter by not acknowledging espionage­—but there are stories of espionage hidden behind every headline.”

A portrait of James Jay, who created sympathetic stains, in Fraunces Tavern

By 3 p.m., the lunch crowd has petered out and just a few folks huddle around dark stouts. It looks like the owners have proudly done little in the way of modern renovation, and the wooden floors creak with every step. It’s thrilling to imagine that roughly 240 years ago Washington was operating out of this building and meeting with the Sons of Liberty here. This is also where he delivered his famous farewell address after the British evacuation of New York and where either Samuel Fraunces (a suspected spy) or his daughter foiled a Washington assassination plot: a poisonous pea plate served by one of Washington’s bodyguards.

Sipping on a Diet Coke in one of the booths, Melton explains that back then, Washington relied on messages written in “sympathetic stains,” which required one chemical to write the message and a second to see it. Washington also employed ciphers and codes (“38” meant attack, “711” meant George Washington). A female spy was even known to hang laundry that conveyed covert messages depending on the number of handkerchiefs or the color of her petticoat. “This is traditional tradecraft,” he explains, “and absolutely foolproof. Spies are always using new technology, but some of the oldest [methods] are the hardest to detect.” That could mean a ribbon tied to a tree branch, a thumbtack stuck to the bottom of a staircase bannister or a white chalk mark on a green sidewalk barricade. All are innocuous enough, but they could signal that a meeting or drop site is activated or terminated. As technology improves and the FBI hunts for digital clues, Melton says the most successful covert intelligence still incorporates traditional tradecraft.

Starbucks on Hanover Square

We make our way a few blocks north on Pearl Street to the Starbucks on Hanover Square, where a half-dozen patrons are sipping hot drinks and languidly scrolling through their phone feeds. There are more than 240 Starbucks locations in Manhattan alone, but this is the one that Russian spy Anna Chapman (born Anna Vasil’evna Kushchenko, daughter of a senior KGB agent) had gone in 2010 to communicate with a person she believed to be a Russian agent. Melton points to the coffee shop’s southeast corner, where a couple speaks Portuguese today, but 10 years ago, security cameras captured Chapman meeting with an FBI agent posing as a Russian intelligence officer. Gaining her trust with a code word, he told her to deliver a fraudulent passport and later leave a postage stamp on the Citi Bike map outside to signal that she’d completed the operation. She’d use a special program on her Toshiba laptop with a “range extender” to bypass the Internet. The FBI agent also convinced her to hand over her laptop for an upgrade that would help covert efforts.

Later that day, Chapman grew suspicious, purchased a burner phone and tossed the phone’s paperwork in a nearby trash can, which the FBI quickly retrieved, allowing them to track the phone. Melton explains using a public trash can was flawed tradecraft, but even so, the 28-year-old redhead’s ability to mingle with celebrities and seduce influential men (the FBI had records of at least five significant suitors) had a senior FBI counterintelligence official predict that within six months [she] would have been the most dangerous Russian spy in America.

 In June 2010, Chapman was one of ten Russian intelligence officers arrested by the FBI in New York, Boston, New Jersey, Northern Virginia and Seattle.

I ask Melton how the FBI was tipped off about Chapman in the first place. He flashes a sly smile. “The only way a spy is caught is if a human source betrays them or there’s an electronic penetration,” he says. “How Anna was caught is still a secret.”

At some point in the 1970s, CIA agent Frank Terpil went rogue, trading overvalued Indian rupees in Afghanistan banks for dollars. After he was fired, Terpil went on to illegally provide arms to Libya and sold $3.2 million in guns to Uganda. But his gunrunning ended in 1979 at a suite at the New York Hilton on Sixth Avenue in Midtown when two undercover NYPD detectives, posing as Latin American revolutionaries, paid Terpil a $56,000 deposit for 10,000 machine guns.

Today, Melton and I are perched at a round table overlooking the spacious lobby as guests line up to check out and staff remove holiday decorations from the banisters. According to Melton, it’s not hard to get an agent to lose their way, and he recites the handy acronym MICE: money, ideology, compromise and ego. Terpil’s vice was money, along with “nice things and gin.”

“Terpil was a traitor but he wasn’t a double agent,” Melton clarifies. “Double agents are incredibly rare—you have to be recruited as an agent by an intelligence service and then by another.”

As we stroll through Midtown, Melton offers more insight: Theaters, such as the nearby Radio City Music Hall, are common meeting sites because they are often dark, with access to public transportation and multiple exits. During the height of the Cold War, a CIA officer developed what’s now known as the “brush pass,” a rapid, undetectable exchange of a package or document between two people in a crowded public place. The move was perfected in the stairways and congestion at Grand Central Terminal before the CIA taught a Czechoslovakian agent to use it to pass them classified information.

“Even if you have surveillance, there’s no way of knowing a meeting ever took place,” Melton says.

Crossing Sixth Avenue, Melton leads me past the iron gate to the storied ‘21’ Club, where servers in white jackets shuttle chicken hash and steak tartare to the well-to-do. During Prohibition, the downstairs wine cellar notoriously operated as a speakeasy, which explains why it’s hidden behind a 2.5-ton secret door that uses an 18-inch meat skewer as a key. There, you’ll find the untouched personal wine stock of Elizabeth Taylor, Presidents Nixon and Ford, and Chelsea Clinton. Though this seems the ideal setting for a covert meeting, Melton tells me that the spies actually hung out upstairs at the bar in the main dining room during WWII, including the head of the Office of Strategic Services (a precursor to the CIA), representatives of MI6’s British Security Co-ordination organization, intelligence-officer-turned-James-Bond-author Ian Fleming and even suspected German spies.

The '21' Club's wine stock includes bottles owned by celebrities and presidents

It seems obvious that alcohol, highly classified intelligence and enemy agents should remain mutually exclusive, but all three intersected here with little drama. “There was no formal neutrality,” Melton explains. “They were drawn and attracted to the legendary location.” Printed cards stating “Be careful with your speech” were known to be passed around if an officer started divulging too much. “It’s very possible that happened here,” Melton says. “Loose lips sink ships.”

We head three blocks north to The St. Regis hotel’s King Cole Bar, where in the opulent, wood-paneled lounge, a bartender whips up the signature cocktail for the past 86 years: the Red Snapper (now known as a Bloody Mary). An interior designer is holding a lunch meeting in one corner of the bar, so Melton and I duck into a lacquered booth on the opposite end, where he explains in a whisper that American and British spymasters often met here during WWII. With the dark booths, stiff drinks and lavish Maxfield Parrish mural running the length of the bar, it’s not hard to see why they liked it here. In fact, in Fleming’s Live and Let Die, he calls it the “best hotel in New York.” (However, in the novel, Bond stays in room 2100, even though there are only 20 floors.)

After downing our drinks, Melton and I head west to the steel globe sculpture at Columbus Circle, where, Melton tells me, two Russian spies set out to rendezvous in 2004. They had agreed to identify themselves with the verbal cue “Uncle Paul sends his love,” but with five different subway lines converging at the Circle, the area proved quite chaotic, and the two Russians waited hours before giving up on meeting (one stood by the stairs, the other underneath the globe). When they returned the next day and found each other, Melton says they walked to a nearby bench in Central Park, where they talked for two hours. “They opened up to each other about pressure they were under and finally felt like they had found someone to talk to,” says Melton. “This is the first time in history that we know of two Russian illegals ever meeting in an operational country.” The FBI had been surveilling the meeting, and the foreign agents were eventually arrested with Anna Chapman.

The Maxfield Parrish mural at The St. Regis' King Cole Bar

We stroll through the park as the sun starts to set. Every few steps, Melton points out a crumpled soda can or a rock that may be hollowed out to hide intelligence. “The CIA even used a dehydrated rat with a Velcro stomach,” Melton explains. At the park’s famous Tavern on the Green restaurant, he says another Russian illegal officer used to mark the menu sign as a signal site. We both eye the single white mark on the lower right corner suspiciously and laugh.

It’s been a long day and I assume Melton must be exhausted after walking around the city with his cane. He’s getting ready to hail a taxi on Central Park West when he reveals that he’s trained as a “cane master,” or someone who knows how to use a walking stick as what he refers to as a “personal protection device.” He points out the sharp edge on one side, then swings into action, whirling the wooden cane over his head like a pair of nunchucks. “It takes 1.8 seconds to access a weapon on your holster,” he says matter-of-factly. “This is always in my hand.”

Before I can properly register what just happened, the senior citizen slips into a cab and disappears.

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