His son Robert Jr. confirmed the death. Sweet, who lived in Manhattan, also had a home in Ketchum, where he was on vacation. At his death he was a senior federal judge in the Southern District of New York.
Sweet was Lindsay’s chief deputy mayor (and had been his former Yale Law School roommate) from late 1966 through 1969, representing the mayor in tense labor disputes.
These included a teachers’ strike in 1967 that kept most of the city’s 1 million public school students out of school for 2 1/2 weeks, and a nine-day sanitation workers’ strike the next year that left garbage piled up throughout the city.
Those fights, largely over wages and working conditions, were nothing new in New York City’s long history of labor relations. But three later strikes by the teachers in the fall term of 1968 proved far more intractable, because they revolved around who would control the schools.
The strikes, which emptied classrooms for a total of eight weeks, grew out of a plan intending to improve public education by decentralizing the city’s school system. Pilot projects had been set up in three school districts, including Ocean Hill-Brownsville, in a predominantly black and Puerto Rican area of Brooklyn.
The strikes were called after the district’s board had summarily moved to transfer a group of teachers and administrators out of the district. Ten of the teachers resisted, but the board persisted even after a trial examiner for the school system did not find enough evidence to support the board’s accusations that the 10 had tried to sabotage community control or had done unsatisfactory work.
The teachers’ union saw itself in a must-win fight to protect its members’ rights and discourage such actions by other local boards. Many supporters of the district’s leadership, which was largely black, saw the strikes as an effort by a largely white and heavily Jewish union to squelch community control. Anti-Semitic and racist accusations punctuated the conflict.
Sweet, on Lindsay’s behalf, sought to persuade the union, the district’s leadership and the Board of Education to compromise. Though he won praise for his low-key manner and his ability to relieve tensions in the negotiations — Sid Davidoff, an assistant to the mayor, told The New York Times that Sweet “can deal with anybody, even an adversary, in almost a friendly way” — only the state was able to end the conflict. It suspended the district board, and the involuntary transfers were made subject to grievance procedures in the union’s contract.
Sweet’s cordial negotiating manner — the “Sweet schmooze,” City Hall colleagues called it — was also an asset in Albany, New York, where he often traveled to appeal for more state financial aid for the city.
Sweet stepped down as deputy mayor at the end of 1969, after Lindsay was elected to a second term, and returned to private law practice as a partner at Skadden, Arps, Slate, Meagher and Flom. President Jimmy Carter named him to the U.S. Court for the Southern District of New York, in Manhattan, in 1978.
One of Sweet’s major rulings came in 1992, when he declared that the state’s law against begging on the streets was an unconstitutional violation of free speech.
While the government has a “valid interest” in preserving public order, he said, “the interest in permitting free speech and the message that begging sends about our society predominates.”
He added, “A peaceful beggar poses no threat to society,” while “aggressive panhandling” could be prosecuted under existing laws.
The ruling was upheld on appeal. In 1996, New York City enacted its own ban on aggressive panhandling. Panhandling remains illegal in the city’s subways and buses and at Transit Authority stations.
Perhaps Sweet’s most controversial words were expressed off the bench. In a 1989 speech at the Cosmopolitan Club in Manhattan, he called for legalizing heroin, crack cocaine and all other illegal drugs.
The war on drugs was “bankrupt” and futile and overwhelming the courts, he maintained. If legalized, he said, the drugs could be produced by pharmaceutical companies, regulated like alcohol and kept unlawful for minors.
Those advocating legalization expressed gratification at having a federal judge on board. Critics argued that Sweet was defeatist, and that heroin and crack were more addictive than alcohol.
In another prominent case, Sweet, in 2003, dismissed a lawsuit that sought to hold the McDonald’s Corp. liable for obesity and ill health in teenagers.
‘If a person knows or should know that eating copious orders of supersized McDonald’s products is unhealthy and may result in weight gain,” Sweet wrote, “it is not the place of the law to protect them from their own excesses.”
He went on to note: “Nobody is forced to eat at McDonald’s. (Except, perhaps, parents of small children who desire McDonald’s food, toy promotions or playgrounds, and demand their parents’ accompaniment.)”
Robert Workman Sweet was born in Yonkers, New York, on Oct. 15, 1922, the son of James and Delia (Workman) Sweet. His father was a lawyer.
Sweet attended the Horace Mann School in the Bronx and the Taft School in Connecticut before graduating from Yale in 1944. He spent two years in the Navy, commanding a submarine chaser in the Atlantic, his family said. He graduated from Yale Law in 1948.
That same year he married Lois Clapp. The marriage ended in divorce. In 1973 he married Adele Hall Leopold, a daughter of Dorothy Schiff, at the time publisher of The New York Post. Adele Sweet was assistant publisher of The Post under her mother and later headed the Dorothy Schiff Foundation. Adele Sweet died in December at 93.
In addition to Robert Jr., Sweet is survived by two daughters, Deborah Given and Eliza H. Sweet; another son, Ames; seven grandchildren; four great-grandchildren; six stepchildren; and many step-grandchildren and step-great-grandchildren.
After law school Robert Sweet worked largely in private practice for 17 years. He was also active in Republican Party politics and served as Manhattan borough coordinator in Lindsay’s first race for mayor, in 1965. The victorious Lindsay brought him to City Hall as his executive assistant, and made him chief deputy mayor after a year.
Among Sweet’s many former law clerks was former Gov. Eliot Spitzer of New York.
In his later years Sweet was an avid figure-skater, beginning many days with a morning skating session at the Chelsea Piers Sky Rink in Manhattan. He started skating after his wife, Adele, a skater herself, gave him figure skates as a birthday present.
“Figure skating is often precarious at any age, and the fact that the judge does this at 92 is extraordinary,” an instructor, Marni Halasa, told Corey Kilgannon of The New York Times one morning in 2015 for an article about the judge’s hobby.
The judge proceeded to practice a fox trot ice-dance routine as well as maneuvers like swing rolls, 3-turns, Mohawk turns and crossovers.
Robert Sweet saw parallels between skating and judging.
“You really have to pay attention to detail, and it requires balance and hard work,” he said. “It doesn’t make me a better judge or anything like that, but working hard at anything makes you better.”
This article originally appeared in The New York Times.