BOSTON – Bob Woolf, who pioneered the role of the sports agent in the late 1960s and represented stars from Larry Bird to Carl Yastrzemski, died of a heart attack Tuesday on his boat off Fisher Island, Fla. He was 65.

He died in his sleep and was pronounced dead at South Shore Hospital in Miami Beach, Fla., the Dade County Medical Examiner’s Office said.

His best-known clients were basketball stars: Bird, John Havlicek, Julius Erving, Marvin Barnes and Robert Parish. Baseball players he represented included Yastrzemski, Thurman Munson, Mark Fidrych, Ken Harrelson and Ruben Sierra. He also was the agent for football players Jim Plunkett, Raghib “Rocket” Ismail; and hockey players Jim Craig and Derek Sanderson.

Woolf also was the agent for New Orleans Saints quarterback Mike Buck, who starred for the University of Maine from 1986 to 1989.

Bird said Woolf was like a father to him, especially in 1979, when Bird entered the NBA.

“He told me what was going to happen and it always happened that way, so I always felt prepared,” Bird said in a statement released by Woolf’s office. “In the beginning, it was a business relationship, but it grew into a great friendship. He really cared about the happiness of his clients and I am grateful to him for his guidance and friendship.”

In addition to sports, Woolf represented media personalities who included Larry King, Gene Shalit and the late Pete Axthelm. He also was the agent for the music group New Kids On The Block, and said two years ago that they brought in more money that any other client.

“Bob Woolf was an even better friend than he was an agent, and he was a terrific agent,” King said.

Known for remaining pleasant even in the toughest negotiations, Woolf wrote the book on the subject, “Behind Closed Doors.”

“I know every contract of every professional ballplayer in America,” Woolf said in 1983.

Woolf became one of the nation’s first sports agents when Boston Red Sox pitcher Earl Wilson asked him to handle off-field activities, including product endorsements and speaking engagements, in 1965. In 1966, Woolf represented Wilson in contract negotiations, at the time an unprecedented role for a player’s lawyer.

“He was one of the first people in what is now known as sports law,” said Peter Roisman, an agent who represented the late Reggie Lewis. “He was a trailblazer and what he did benefited players immensely, and will continue to benefit players.”

In 1971, Woolf closed his law practice and began to represent athletes and celebrities exclusively. He maintained offices in Boston and Miami.

In addition to negotiating contracts, Woolf managed clients’ finances. Some athletes, including Barnes and Erving, fired Woolf because of his refusal to renegotiate for more money in the middle of their contracts.

“He always had the athlete at heart when he represented you,” said Havlicek, who was represented by Woolf from the time he signed his first contract with the Boston Celtics.

“He created a set of ethical standards that very few of his colleagues in the business were adhering to,” said Richard Lapchick, director of the Center for Sport in Society at Northeastern University. “It was a very murky enterprise that really ended up derailing the life potential of so many pro athletes who have littered the landscape with horrible tales of financial bankruptcy.”

Lapchick used Woolf as a case study in his book “The Rules of the Game,” about ethics in sports.

“He really was a lover of sports, as opposed to simply using it to gain his livelihood,” Lapchick said.

Even those who sat on opposite sides of the negotiating table praised Woolf Tuesday.

“Bob Woolf was a paragon of the sports representation field,” said Steve Ortmayer, the director of football operations for the Los Angeles Raiders. “His ability to make a deal, not defeat one, has served his clientele well and stood the test of time. He will be missed in our business.”

Born in Portland, Maine, the son of Jewish immigrants, Woolf grew up on Munjoy Hill and graduated from Portland High School.

Woolf attended Boston College on a basketball scholarship. He went to law school at Boston University.

Woolf is survived by his wife, Anne, and three grown children. A funeral is scheduled for Friday at Temple Emeth in Brookline, Mass.