By 1988, Nick Littlefield had mastered much of the legal profession’s most challenging repertoire. He had prosecuted drug dealers in New York City, taught at Harvard Law School, worked at a prestigious Boston firm, and served chief counsel of the Ward Commission, investigating corruption in public construction contracts.
Then Senator Edward M. Kennedy offered him a job. Mr. Littlefield, who was 74 when he died Saturday in his Cambridge home of complications from multiple system atrophy, recalled the moment he said yes in “Lion of the Senate,” his 2015 book about his years with Kennedy.
“He took me out onto the balcony, turned to glance up and down Constitution Avenue, over the Capitol, the Supreme Court, the Washington Monument, and, in the distance, the rows of graves in Arlington National Cemetery, where both his brothers were buried,” Mr. Littlefield wrote of that meeting in Kennedy’s Washington office.
“Before I could say anything, he asked me when I could start,” Mr. Littlefield added. “I said, ‘How soon do you need me?’ ”
For the next decade, he was Kennedy’s chief of staff for health care and served as chief counsel of the Senate Health, Education, Labor and Pensions Committee. During those years, among the most fruitful of Kennedy’s tenure, Mr. Littlefield helped shape a series of far-reaching health care bills the senator sponsored or shepherded, including the Americans with Disabilities Act and the Family and Medical Leave Act, along with the first minimum wage increase since 1981.
“Something incredible happened during that time,” said Vicki Kennedy, the wife of Senator Kennedy, who died in 2009. “The amount of legislation that was put through that improved people’s lives was just extraordinary.”
With the senator, Mr. Littlefield forged more than just legislation that affected tens of millions of lives.
“They became tremendous friends. They both had this conviction and commitment to make the world better,” Vicki Kennedy recalled, adding with a laugh that they also “both loved to sing. Nick’s voice was better, but Teddy would never give that to Nick.”
While socializing, sailing, and singing together, they bonded through “their enjoyment of life,” she said. “This joy — you just don’t see it that often.”
Mr. Littlefield, however, was equally capable of using his serious side when circumstances required. During the Ward Commission hearings at the end of the 1970s, he could turn silence into a forceful tool. “Nick would ask his question, then stare for what seemed an interminable time,” the late John William Ward, for whom the commission was named, told the Globe in 1979. “The silence even made me nervous. All of a sudden, the witness would start talking.”
Thomas E. Dwyer Jr., a former Boston Bar Association president who was deputy chief counsel for the commission, called Mr. Littlefield “a tremendous leader.”
In an era when persistent corruption had frayed the public’s trust, “he made everybody understand that they had to do the right thing,” Dwyer said. “And he also set up a scenario that was unheard of: zero political influence whatsoever.”
Bancroft Littlefield Jr., known to all as Nick, was the son of Bancroft Sr., a lawyer in Providence, and the former Anne Davidson. Mr. Littlefield grew up in Providence, where he attended the Moses Brown School, and graduated from Milton Academy before going to Harvard College.
A singer who performed with Harvard’s Hasty Pudding Club, Mr. Littlefield spent a year as a professional actor, after graduating in 1964. He was in “My Fair Lady” summer stock productions and appeared in a revival of “Kismet” at Lincoln Center in New York City before attending the University of Pennsylvania Law School.
“He had some heady moments,” said his wife, Jenny, “like when Noel Coward came to a Hasty Pudding show and said to him after, ‘You’ve got a lot of talent.’ ”
Other talents drew Mr. Littlefield to the legal world, but he didn’t want to be “a regular lawyer” like his father. “I wanted to do public service,” he told the Globe in 1979.
During and after law school, he worked on campaigns for Rhode Island’s Republican governor John Chafee and then studied at the London School of Economics. He returned to New York for a job at a corporate law firm, from which he took leaves of absence for political organizing with a lawyers’ anti-Vietnam War group. Then he served as an assistant US attorney for the Southern District of New York, prosecuting corruption, organized crime, and drug dealers “who were part of the infamous ‘French connection,’ ” he recalled in his book.
In 1976, he returned to Boston and was a lecturer at Harvard Law School, where he taught a course called “The Government Lawyer.”
While working with the Ward Commission, Mr. Littlefield married Jenny Lyman in September 1979. She had three children from her previous marriage to Allard Lowenstein, a former congressman and noted civil rights activist. Six months after they married, a mentally ill gunman killed Lowenstein in his New York office.
By day, Mr. Littlefield was directing a high-profile anti-corruption inquiry, and “at the same time, he took superlative care of this very wounded family,” his wife said. “There was never a moment when we didn’t all feel that he was always there for us. I think back and wonder, ‘How do you do that?’ He was there for those children through their rocky time.”
Once the commission’s work was finished, Mr. Littlefield worked at the firm known as Foley, Hoag & Eliot. After his decade with Kennedy, he returned in 1998 to the firm, which is now Foley Hoag, and chaired its government strategies group.
While in Washington, Mr. Littlefield took extensive notes for what would become his book, which he coauthored with David Nexon and finished after being diagnosed in 2011 with multiple system atrophy. At one point, in the hospital and unable to speak, Mr. Littlefield spelled out sentences using a letter board and a drumstick.
“That’s the way he could communicate, and that’s how we did the final edits,” his wife said.
“There’s never been a moment when I wasn’t proud of him,” she added, “and, of course, proud of how he handled his illness.”
A service will be announced for Mr. Littlefield, who in addition to his wife leaves his stepchildren, Frank Lowenstein of Washington, D.C., Tom Lowenstein of New Orleans, and Kate Lowenstein of Brighton; two sisters, Anne of Princeton and Mary of Concord; and six grandchildren.
“I consider myself to be one of the luckiest men alive,” Mr. Littlefield wrote in a 2014 Harvard class report, when he was well into the illness and could no longer sing, as he had at a celebration of Edward Kennedy’s life in 2009. That night, Mr. Littlefield serenaded the crowd with “Love Changes Everything” — a song the senator had often encouraged him to sing.
“Teddy loved the way Nick sang it,” Vicki Kennedy said. “It would get higher and higher with each additional verse. We’d be on the boat and Teddy would say, ‘Sing that song,’ and Teddy would conduct him with his hands, going up, up, up, up.
“And when Teddy got sick, Nick would sing that song to him.”
Bryan Marquard can be reached at firstname.lastname@example.org.