Haviland Smith, who helped CIA officers avoid detection, 94

Soon after he arrived in Prague in 1958, Haviland Smith discovered he was under constant surveillance, followed by secret police through the city’s narrow streets, alleys, and arcades. Even when he thought he was free, a pair of eyes always seemed to be on him: After one uneventful trip around the capital, he learned from intercepted radio chatter he had been watched by more than two dozen vehicles.

there was a reason for all the attention. mr. Smith, a multisport athlete with a knack for languages, was working as the CIA station chief, managing agents across communist Czechoslovakia. He was only in his late 20s, a relative newcomer to the Cold War struggle. But on his walks through the city, meandering down the road with police on his trail, he began to develop ideas about how to operate in the hostile, heavily surveilled locations known in spy-speak as denied areas.

Experimenting in Prague and in Berlin, mr. Smith helped broaden the tradecraft of espionage, pioneering simple but effective techniques CIA officers could use to evade detection in Eastern Europe and the Soviet Union. His work drew the admiration of colleagues including tony mendez, a master of disguise celebrated in the film “Argo,” and his wife, Jonna mendez, who later ran the CIA disguise unit.

“Essentially what Smith had done was to prove that there were no such things as denied areas; it was simply a question of methods,” the mendezes wrote in “the moscow Rules,” a book about the tactics that CIA operatives adopted for the Cold War. “If the right techniques were used, anything was possible.”

mr. Smith, who retired in 1980 after a 24-year CIA career, was 94 when he died June 20. His death, at home in monroe township, N.J., was confirmed by his wife, Dolores Smith, who said he had chronic obstructive pulmonary disease and was recently treated for COVID.

Looking back on his career, mr. Smith was quick to dispel the idea that it was nonstop adventure, a James Bond movie come to life. the world of espionage, he once wrote, was “demanding, confusing, often boring, and occasionally wildly exciting.”

Working undercover as a diplomat, he spent five years in the middle East, where he was stationed in Beirut (he called the capital “a terrific place to hunt Soviets”) and in tehran before the Iranian revolution. He later led the CIA’S counterterrorism staff, keeping tabs on militant groups such as Europe’s Red Army Faction and Red Brigades, and served as an executive assistant to CIA Deputy Director Frank Carlucci, who became secretary of defense under President Reagan.

to colleagues at the agency’s Langley, va., headquarters, he remained best known for his contributions to tradecraft, along with “his knowledge about recruitment and development operations” targeting the Soviets, said John macgaffin, a former No. 2 official in the CIA.

mr. Smith had served for three years in the Army Security Agency, intercepting Russianlanguage messages, before joining the CIA in 1956. that experience proved to be crucial in Prague, where he was able to locate the radio frequency used by Czech security forces and crack their code, according to “the Billion Dollar Spy,” Washington Post journalist David E. Hoffman’s 2015 book about a Soviet electronics engineer who shared documents with the West.

Before mailing a letter or making a dead drop, in which he left a message or package at a secret location, mr. Smith would turn on the radio and record the security broadcasts. After he returned, he would listen to the tape to see if he had been followed — and cancel the rest of the operation if he had.

Early on, when he noticed he was being followed, he tried to outpace the secret police. that method backfired: Whenever he got away from one surveillance team, speeding down the street to get away from the watchers, he’d find himself surrounded by reinforcements.

mr. Smith’s chief innovation involved no fancy spy gear or 007-style stunts. to get around the police, he simply lulled them into passivity. “He became boring,” the mendezes wrote, “what we call a ‘little gray man.’”

For months, he maintained a clockwork schedule, taking the same routes to drive the babysitter home each evening and get his hair cut every other week. Gradually, his minders stopped paying close attention during the trips, creating a window in which he could deliver a message or make a dead drop, so long as he didn’t stray too far from his routine.

to give himself additional freedom while “working in the gap,” as he put it, he began rounding corners. By making two right turns in quick succession, he could create at least 15 seconds of separation from surveillance teams trying to catch up. He later refined a technique known as the brush pass, in which he surreptitiously delivered a package to an agent who would leave down an escape route, walking one direction while mr. Smith went another.

Some officials remained skeptical of his tactics. Richard Helms, who led clandestine operations for the agency, refused to approve the use of the brush pass in Prague in the mid-1960s, arguing that it was too risky for officers to come in direct contact with agents there rather than keeping a distance and communicating through dead drops.

After more than a year of advocating for the brush pass, mr. Smith organized a demonstration one day in 1965, arranging for Helms’s deputy, thomas Karamessines, to meet him in the lobby of Washington’s historic mayflower Hotel.

Sitting on a bench with Bronson tweedy, the head of the CIA’S Eastern European division, Karamessines watched as a case officer came through the door, approached mr. Smith, and shook out a rain coat.

mr. Smith walked away as his boss grew impatient.

“When are they going to do it, anyway?” Karamessines asked, according to “A Secret Life,” journalist Benjamin Weiser’s 2004 book about another Cold War-era operative.

“tom,” tweedy replied, “they’ve already done it.”

the rain coat had served as a form of misdirection: As the case officer shook it with one hand, he delivered a package to mr. Smith with the other. It was sleight-ofhand that mr. Smith said he learned from a magician.

Soon, the brush pass was approved for much of Eastern Europe operations.

Haviland Smith Jr. was born in manhattan on Aug. 25, 1929, and grew up in Ridgewood. His father was a photographer and art gallery owner, and his mother wrote more than two dozen cookbooks, including “the Four Seasons Cookbook” with James Beard under the name Charlotte Adams. they separated when mr. Smith was about 3.

mr. Smith, who went by Hav, graduated from Phillips Exeter Academy in New Hampshire and received a bachelor’s degree in English and Russian from Dartmouth College, where he played lacrosse and was a goalie for the hockey team. He enrolled at the University of London, where he did graduate work in Russian and was recruited by the CIA.

He was joined on his overseas tours by his first wife, the former martha Allen, and their three sons, Gordon, Holbrook and Haviland III. the marriage ended in divorce.

After he retired, he married Dolores tuohey, a fellow CIA veteran. they had a daughter, Elizabeth, and settled on a farm in Brookfield, vt., where mr. Smith raised fallow deer, foraged for mushrooms, coached girls’ lacrosse, turned wooden bowls on a lathe, and tied his own flies, fishing in nearby lakes and ponds. He moved back to New Jersey about six years ago.