Bob Woolf, the pioneering sports attorney whose management of the financial affairs of Carl Yastrzemski, Larry Bird, Doug Flutie and other athletes ushered in the era of the millionaire sports celebrity, died yesterday, apparently of a heart attack, on his boat off Fisher Island, Fla.
He was 65.
Woolf died in his sleep and was pronounced dead at South Shore Hospital in Miami Beach, the Dade County Medical Examiner's Office said.
Once described by Time magazine as the "Cecil B. DeMille of the Locker Room," he represented his first sports client in 1965, Boston Red Sox pitcher Earl Wilson. He then embarked upon a 28-year career that made him the country's preeminent sports attorney.
His clients included John Havlicek, Julius Erving, Robert Parish, Ruben Sierra, Rocket Ismail and other sports figures as well as Gene Shalit, Larry King and other media personalities, and the pop group New Kids On The Block.
Woolf lived in Brookline, Mass. He was born in Portland, Maine, and graduated from Boston College and Boston University School of Law. Ten years after he started practicing law, he began representing Wilson, shortly after the pitcher had thrown a no-hitter and became overwhelmed by endorsement opportunities.
After Woolf successfuly negotiated a contract and endorsement deals for him, Wilson introduced the lawyer to Red Sox stars Reggie Smith, Yastrzemski and Ken Harrelson.
Woolf's roster of athlete clients soon swelled to include Boston Celtics players Havlicek, Larry Siegfried and Sam Jones. At one time in the late 1960s, he negotiated the finances and contracts of nine of the 12 members of Bill Russell's Celtics.
In 1971, Woolf closed his law practice and started representing athletes exclusively.
He negotiated Derek Sanderson's record-breaking $2.6 million five-year contract with the Philadelphia Blazers of the World Hockey Association in 1973 and handled Flutie's highly publicized negotiations with Donald Trump and the New Jersey Generals of the now defunct U.S. Football league in 1985.
From a Boston office overlooking Fenway Park, Woolf oversaw a staff of 25 that negotiated about 2,000 athletic contracts worth $1 billion.
His office decorations included Bird's Celtics jersey, the bat Yastrzemski used for his last hit in a Red Sox uniform and Flutie's Davey O'Brien Award. In one corner, he kept a telescope he used to check on games in progress in Fenway Park.
During the 1988 presidential campaign, Woolf traveled with Gov. Michael Dukakis and oversaw the last-second negotiations that led to Dukakis' one-on-one interview with Ted Koppel on "Nightline."
He had been a special adviser to President Ronald Reagan's Council on Physical Fitness and Sports, a trustee of the Basketball Hall of Fame, and chairman of the American Bar Association's governing committee for sports and Entertainment Law. He also was a columnist for the National Law Journal.
Woolf was known for his nonconfrontational negotiating style.
"The last thing you want to do is turn a negotiation into a confrontation," he said in his book "Friendly Persuasion: My Life as a Negotiator."
"You want to make it a situation of mutual respect. You'll have a better shot of getting what you want."
He also wrote an autobiography, "Behind Closed Doors."
He was known for his close relationships with his clients.
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 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."