FromNathan “I only regret that I have but one life to lose for my country” Hale, to redheaded sleeper agent Anna Chapman, we’re a city of secrets. NewYork has been home to CivilWarespionage rings,WorldWar I saboteurs andCold War plots, with cryptographers and double-agents in between.
In their new book, “Spy Sites of NewYork City,” H. Keith Melton, a historian, and Robert Wallace, former director of the CIA’s Office of Technical Service, highlight them all. Grab your trenchcoat and fedora and take a tour.
THE CULPER RING
Peck Slip, east side of street near Pearl Street During the Revolutionary War, George Washington and others formed the Culper Ring — perhaps a shortening of Culpepper County, Va., where Washington once worked as a surveyor.
Each member of the ring received aliases as well as code numbers for secrecy and communications. Washington’s number was 711.
Key to the operation was Robert Townsend, number 723, alias Samuel Culper Jr., a New York City merchant. His store, on Peck Slip, was a favorite among British officers who could afford its good assortment of lemons, rum and quality dry goods.
Using an invisible ink called sympathetic stain or white ink, concocted by James Jay, the physician brother of John Jay, Townsend sent a steady stream of secret intelligence fromNew York to Gen. Washington.
Amystery agent, the only woman, is mentioned just once in documents from the time. Known only as 355, her identity has been the subject of debate and speculation. Was 355 the mistress of the brooding Townsend? According to legend, Townsend’s lover was arrested and put aboard the prison ship HMS Jersey, where she gave birth to Townsend’s child. Even as she was dying of privations, the mysterious mistress managed to keep the Culper Ring’s secrets.
HEARD IT AT THE GRAPEVINE
11th Street and SixthAvenue Built in the 18th century, the Old Grapevine Tavern was housed in a three-story clapboard house. Originally called the Hawthorne, the tavern later acquired its better-known nickname from an ancient grapevine growing on one side. Popular with actors, writers, artists, politicians and NewYork’s fashionable men, the Old Grapevine became a Civil War gathering spot for Union officers as well as Confederate spies. The common phrase “heard it through the grapevine” is said to have originated at the drinking establishment.
The tavern was sold in 1912 and, much to the previous owner’s dismay, opened a back parlor where women could sit and drink. The Old Grapevine was demolished three years later, in 1915.
CODE TALKERS
Seventh Avenue betweenWest 50th and 51st streets If you were a newly arrived Russian spy in New York in the 1930s, chances are good you stayed at the Hotel Taft, now the Michelangelo. If your contact at the hotel welcomed you with a parole such as, “Greetings from Fanny,” the required answer would be, “Thank you. How is she?”
THE TALKATIVE GANGSTER
Belmont PlazaHotel, 541 Lexington Ave.
Hopes were high in 1943 amongOSSscientists that tetrahydrocannabinol acetate, a derivative of the cannabis plant, could elicit truth froman unsuspecting subject. To test the potential, an OSSofficer and formerNYPDdetective invited gangster August “Little Augie” Del Gaizo, whomhe knewfromhis previous years in law enforcement, to a roomat the Belmont PlazaHotel, nowtheWNew York Hotel. Thedrug was administered to the unwitting Del Gaizo in a cigarette and appeared to have positive resultswhen the gangster began describing some of his illegal activities.
However, subsequent testing demonstrated the drug wasunreliable and ineffective.Ten years later, the CIA ran“Operation Midnight Climax,”where Russian sailorswere lured by prostitutes to 81 BedfordSt. in Greenwich Village, where theyweredoped with “truth drugs.”
CODE NAME CROOK
Burial Site, Union Field Cemetery, 82-11 Cypress Ave., Ridgewood, Queens US Rep. Samuel Dickstein was on the Soviet NKVD payroll from 1937 to 1940 under the code name CROOK. The congressman must have seemed like a prize asset, sitting in the center of American political power and spearheading an anti-fascist investigative subcommittee. Dickstein, who promised to deliver material on the fascist supporters, German agents and White Russians to his NKVD handler, received $1,250 a month payment for his services.
How much useful intelligence the congressman actually provided to the Soviets is uncertain. Responding to inquiries about Soviet defector Walter Krivitsky, Dickstein delivered only a short memo that read suspiciously close to the defector’s public statements in the media, though he did sponsor legislation to have Krivitsky deported.
Dickstein resigned from Congress in 1945, after more than 20 years in office. He then served as a judge on the NewYorkState Supreme Court. His intelligence efforts attracted no suspicion and were not made public until discovered in the archives in Moscow in the early 1990s.
THE BLACK CHAMBER
141 E. 37th St.
America’s first codebreaking organization began in 1912 in a nowdestroyed townhouse belonging to society figure T. Suffern Tailer.
During World War I, it became the Army cryptographic section of Military Intelligence (MI- 8). After the war, the organization was renamed the Cipher Bureau, or Black Chamber, and operated as a joint effort of the State and War departments.
Operating under a business cover of the Code Computing Company, its real businesswas in breaking the diplomatic communications of other nations. The highly successful code-breaking efforts were led by cryptographer Herbert O. Yardley. Yardley’s organization continued until 1929, when Secretary of State Henry L. Stimson famously declared, “Gentlemen do not read each other’s mail.”
Two years later, Yardley published a book-length account of the secret operation called the American Black Chamber, revealing manycryptographic successes against foreign governments, most notably Japan. Yardley continued writing and produced a book of puzzles called Yardleygrams.
GERMANY’S MASTER SABOTEUR
NewYork Yacht Club, at 37W. 44th St.
Possibly the most imaginative saboteur of World War I operated in New York City. Capt. Franz Dagobert Johannes von Rintelen, a former Deutsche Bank executive and German naval intelligence officer, arrived in New York using a false Swiss passport in April 1915. At his disposal was $500,000 ($11 million in current value) to disrupt the flowof American munitions to allies.
Checking in to the Great Northern Hotel (now Le Parker Meridien), von Rintelen opened an import-export front company on Cedar Street under the name E.V. Gibbons. However, it was necessary for him to use his true name at the NewYork Yacht Club, wherehis membership predated the war.
Working with a chemist from Hoboken named Dr. Scheele, the pair devised timed explosive devices, using an interned German ship in NewYorkHarbor, the Friedrich der Grosse, as a bomb factory. Under international law, the ship was treated similarly to embassies, allowing them to work undisturbed.
Von Rintelen then recruited dockworkers to plant the bombs in ships’ coal bunkers. Numerous ships that sunk in the Atlantic during the time can be attributed to vonRintelen’s efforts.
Von Rintelen was also implicated in the 1916 munitions depot explosion at Black Tom Island — a thin peninsula that jutted out intoNewYork Harbor fromtheNewJerseyside. So powerful was the blast, windows in Manhattan were shattered and the Statue of Liberty sustained shrapnel damage.
Unfortunately for von Rintelen, his cover unraveled after a fewmonths. His communications were compromised by Room 40, the code-breaking section of the British Admiralty. He fled, but was arrested and jailed in England.Hereturned to theUSand received a four-year sentence.
LITTLE SHOP OF ESPIONAGE
718Madison Ave.
Velvalee Dickinson arrived in New York during the Great Depression. First taking a job in the doll department at Bloomingdale’s, she subsequently opened her own doll shop. By the time Japan bombed Pearl Harbor in December 1941, the doll shop was failing, yet, inexplicably, the couple always seemed to have plenty of money for trips to the West Coast.
Then, in 1943, some American residents unexpectedly began receiving strange “return to sender” mail addressed to an Inez Lopez de Malinali in Buenos Aires. The letters mysteriously bore US return addresses of people with no knowledge of the correspondence.
The contents, detailing doll sales, aroused suspicion, and a few were turned over to the FBI. From analysis of the letters, the FBI identified de Malinali as a Japanese intelligence contact in Buenos Aires and traced the letters back to Dickinson.
Something was hidden in the letters, but what? Breaking the “doll code” fell to Elizebeth Friedman, a veteran cryptographer, who discovered that each doll mentioned in the letters was a code for a specific type of American warship. Dickinson’s intelligence hadbeen gleaned from trips to the West Coast, where she observed shipyards.
Authorities apprehended a kicking and screaming Dickinson in January 1944 at her bank, where a large amount of money was discovered in her safety deposit box. Sentenced to 10 years inprison, she was paroled in 1951, vanished from sight in 1954, and reportedlydied in 1980.
THE NEW RUSSIAN SLEEPERS
Anna Chapman Residence, 20 Exchange Place When the FBI operation GHOST STORY rolled up 10 Russian intelligence officers in June 2010, the story made international headlines.
Media attention quickly focused on the photogenic Anna Kushchenko Chapman (right), who lived on the 52nd floor in a fashionable Financial District high-rise. The 28-year-old redhead established cover as an Internet real-estate entrepre neur. After the 10 were returned to Russia as part of spy swap, Chapman evolved into a national herowith her own television show, “Secrets of the Worldwith Anna Chapman.”
The press treated the arrests as a joke, but the reality was otherwise. All of the illegals were dedicated, trained officers of the SVR, Russia’s successor to theKGB’s first directorate. An encrypted memo from Moscow to the Murphys, intercepted by the FBI, clarified their mission: “Your education, bank accounts, car, house, etc.—all these serve one goal: to search and develop ties in policymaking circles in US and send reports to the Center.”
GERMANY’S MASTER SABOTEUR
NewYork Yacht Club, at 37W. 44th St.
Possibly the most imaginative saboteur of World War I operated in New York City. Capt. Franz Dagobert Johannes von Rintelen, a former Deutsche Bank executive and German naval intelligence officer, arrived in New York using a false Swiss passport in April 1915. At his disposal was $500,000 ($11 million in current value) to disrupt the flowof American munitions to allies.
Checking in to the Great Northern Hotel (now Le Parker Meridien), von Rintelen opened an import-export front company on Cedar Street under the name E.V. Gibbons. However, it was necessary for him to use his true name at the NewYork Yacht Club, wherehis membership predated the war. Working with a chemist from Hoboken named Dr. Scheele, the pair devised timed explosive devices, using an interned German ship in NewYorkHarbor, the Friedrich der Grosse, as a bomb factory. Under international law, the ship was treated similarly to embassies, allowing them to work undisturbed. Von Rintelen then recruited dockworkers to plant the bombs in ships’ coal bunkers. Numerous ships that sunk in the Atlantic during the time can be attributed to vonRintelen’s efforts. Von Rintelen was also implicated in the 1916 munitions depot explosion at Black Tom Island — a thin peninsula that jutted out intoNewYork Harbor fromtheNewJerseyside. So powerful was the blast, windows in Manhattan were shattered and the Statue of Liberty sustained shrapnel damage.
Unfortunately for von Rintelen, his cover unraveled after a fewmonths. His ommunications were compromised by Room 40, the code-breaking section of the British Admiralty. He fled, but was arrested and jailed in England.Hereturned to theUSand received a four-year sentence.
THE FBI’S DOUBLE AGENT
Knickerbocker Hotel, 42nd Street and Broadway
In the late 1930s, William Sebold held a good job as a mechanic at a California company, Consolidated Aircraft. The native German, born Wilhelm Georg Debrowski, fought in WWI as a machine gunner but later jumped ship in Galveston, Texas, changed his name, married and became a naturalized US citizen. On a visit to Germany in the summer of 1939, Sebold’s life took an unexpected turn when he was approached by German intelligence to spy on America. After agreeing to do so, Sebold reported the “recruitment” to the American consulate in Hamburg.
Acting on German instructions to handle communications for an existing group, the Duquesne spy ring, Sebold set up a front company in the Knickerbocker Hotel, which the FBI wired with microphones and movie cameras. Over the next 18 months, the double agent made hundreds of shortwave radio transmissions from a site on Long Island, using the call number CQDXVW-Z. The FBI-controlled radio station transmitted 300 messages to Germany and received more than 200 replies.
Through Sebold, the FBI identified dozens of German agents in the US, Mexico and South America.
When they eventuallymoved against the German network, more than 30 German spies were arrested and convicted in a trial that concluded less thanaweek after the bombing of Pearl Harbor. His mission complete, Sebold received a new identity fromthe US government in an early version of the witness relocation program and wasmoved to an undisclosed location. He is reported to have died in California in 1970.