He became the so-called “superchief” of a reorganized MBTA in 1975, extending subway lines and diversifying the workforce by gender and race. A few years earlier, he had arrived in Boston as a deputy mayor under Kevin White and was responsible for keeping the public safe at the outset of court-ordered busing to desegregate schools.

Mr. Kiley, who was 80 when he died Tuesday in his Chilmark residence from complications of Alzheimer’s disease, filled his resume with jobs that would be capstones in the careers of many public servants.

As Robert Kiley contemplated running for Boston mayor in the early 1980s, he took note of his qualifications in a manner that could hardly have been more understated. “I wouldn’t be a neophyte, a novice,” he offered, adding, “I know government as well as anyone in my generation. I have served at all three levels: federal, state, and local.”


And before that? Mr. Kiley cut his teeth in government service as a CIA agent. He assisted in the covert funding of student groups and foreign youth until a magazine article blew his cover and he switched to serving as executive assistant to the agency’s director.

In all those jobs, colleagues recalled him as the calm in the center of often swirling storms. “I preferred staying low-key because I find you get a lot more done that way,” he told the Globe.

The storms he weathered weren’t always metaphoric. Mr. Kiley “put together a superb team which for four years gave the T strong new leadership,” Michael S. Dukakis, who as governor appointed Mr. Kiley CEO of the Massachusetts Bay Transportation Authority, said in an e-mail. “The T didn’t collapse during the Blizzard of 1978. It stepped up and provided thousands of people with solid public transportation at a time when the city was virtually paralyzed.”


During his 1983 bid for Boston mayor, Mr. Kiley dropped out when his poll numbers languished in the low single-digits. New York Governor Mario Cuomo then appointed him to run New York’s Metropolitan Transit Authority.

At the time, the nation’s largest transit system “was completely covered with graffiti – 6,200 cars, 480 stations, the depots, the shops,” Mr. Kiley told The New Yorker for a 2004 profile. “It was a kind of leprosy.” He instituted a zero-tolerance policy for graffiti and fare-beaters and implemented a host of improvements. Ridership, which had declined in the years before he took over, rebounded during his seven-year tenure.

Mr. Kiley (left) and Ira Jackson, aides to Boston Mayor Kevin White, viewed a document in 1974. Globe Staff/File

In 2001, a decade after leaving the New York transit job, Mr. Kiley was recruited by Ken Livingstone, London’s then-mayor, to become that city’s first commissioner of transport. Mr. Kiley couldn’t resist trying to breathe new life into the world’s oldest subway system, after having done the same in Boston and New York. “This is like Mount Everest,” he told the Globe in 2001. “How could I say no?”

Robert Raymond Kiley was born in Minneapolis on Sept. 16, 1935. His father, Raymond, was a Woolworth Co. executive. His mother, the former Georgianna Smith, strongly believed in public service, Mr. Kiley told the Globe.

After graduating from St. Thomas Military Academy in St. Paul, Mr. Kiley went to the University of Notre Dame, from which he received a bachelor’s in business administration that “sort of reflected my father’s influence,” he recalled.


While in college, he considered becoming a lawyer, telling the Globe that “three times I got accepted to Harvard Law School, and three times I ended up not going.” Instead, he became president of the National Student Association and then took graduate courses at Harvard for about 15 months before leaving without a degree.

Joining the CIA in the early 1960s, he traveled to 87 countries by the time he was 30, often passing himself off as a US Agency for International Development official, according to The New Yorker profile.

When Ramparts magazine revealed his CIA work, he became executive assistant to the director, Richard Helms. “When I went to the CIA executive suite, I thought I would have an opportunity to see what really went on in government,” he told the Globe, adding that he didn’t much like what he saw and left in part because he was troubled by the Vietnam War.

He was assistant director of the Police Executive Research Forum in Washington before joining White’s administration.

While he was serving as deputy mayor, Mr. Kiley and his wife, the former Patricia Potter, and their two children went on a vacation to Fire Island on Long Island, N.Y. He left early to fly back for work meetings, and while Mrs. Kiley was driving back to Boston, she and their 2-year-old daughter, Jessica, died after their car was struck on Interstate 95 in the Bronx. The couple’s 4-year-old son, Christopher, was badly burned and died later. The family’s baby-sitter was critically injured.


“The world suddenly stops,” Mr. Kiley told the Globe in 1981. “There are either resources there that you can draw on or there aren’t. It is the kind of reserve resources that you don’t check on very often in your life, and you just discover that they are there.”

In 1976, he married Rona Shuman, who formerly was a NAACP Legal Defense Fund executive. They divided their time between Cambridge and Chilmark and have two sons, David of Washington and Ben of Brooklyn, N.Y.

Mr. Kiley “had a huge influence on their lives,” she said, adding that “he was a very special person, and I feel very fortunate that we had all this time together.”

A private service is planned for Mr. Kiley, who in addition to his wife and two sons leaves a sister, Kathleen Goloven of Sarasota, Fla., and a granddaughter.

Known for his analytical approach to reviving three of the world’s largest transit systems, Mr. Kiley attributed his self-discipline at work to his “strong Catholic upbringing” in the Midwest.

In between running the New York and London transit systems, he was president of the Fischbach Corp. construction company, a member of the Kohlberg & Co. private equity firm, and president of Partnership for New York City, a business group.

Upon Mr. Kiley’s arrival in London, a British diplomat toasted him at one gathering, saying: “You are the most important American to come to Britain since Dwight Eisenhower.”


Nevertheless, his hiring by a leftist London mayor popularly known as “Red Ken” was unusual, by the measure of both men.

“I never dreamed I would be trying to recruit a CIA agent,” Livingstone told Mr. Kiley in their first conversation, the Globe reported in early 2001.

“I never expected to be hired by an unreconstructed Marxist socialist,” Mr. Kiley replied.

Robert Kiley (center), with Mayor White (left) at South Station, was dubbed the “superchief” of the reorganized MBTA. Globe Staff/File 1977

Bryan Marquard can be reached at bryan.marquard@globe.com.