This Pioneering Agent Won for His Clients, Sans Making Enemies

They were tied at one set apiece. Jill Leone went up 5-1 in the deciding set. Then Bob Woolf came back.

“He beat me in a tiebreaker 7-5, which is quintessential Bob Woolf,” said Leone, his executive vice president. “He never gave up. It was a beautiful afternoon. The weather was cool and he was feeling great. He was really happy. He beat me. He never gave up.”

Twelve hours after that friendly tennis match in Hollywood, Fla., before the sun rose, she got the phone call. It was 4:30 on a Tuesday morning. Her mentor was found dead on his boat, a heart attack in his sleep.

He was 65.

The pioneer in the sports representation business found ways to win for clients without making bitter enemies of opponents. He never lost the joy in his work as his celebrity and wealth grew.

“I’ve been dreading this day for many years,” said Leone, who learned the business from Woolf, starting as a 22-year-old secretary in 1972. “He used to light up the office.”

Before playing tennis with Sean Connery at a celebrity tournament in Monaco, before appearing on an episode of “Cheers,” before Larry Bird was 10 years old, Woolf was an unknown lawyer laboring on the foundation of a business that would change the sports world.

His office was above Riley’s Roast Beef, a fast-food restaurant on a busy street in a nondescript Boston neighborhood. In 1962, Boston’s Earl Wilson pitched a no-hitter and asked Woolf to handle endorsements.

Ten years later, Woolf could look out the window of his 45th-floor office in the upscale Prudential Building and watch his clients play in Fenway Park.

Twenty years after that, he had offices in Boston, Miami, Spain, Dallas, Los Angeles and New York with about 30 employees. But he still would pinch himself.

He was just a boy from Portland, Maine, the son of Jewish immigrants. Now he was meeting presidents and helping sports superstars become multimillionaires.

“The time I spent with him he was like a little kid around these guys,” said Brad Blank, a Boston agent.

Clients gave Woolf memorabilia for his office: Bird’s uniform from his first Boston Celtics championship, Jim Craig’s stick from the 1980 Olympic hockey win over the Soviet Union, Carl Yastrzemski’s bat from his last hit, five microphones from New Kids On The Block and one from Larry King. Others sent trophies they wanted him to have.

“To him that was really something, that people felt that way and that was important to him,” said Randy Vataha, one of Woolf’s early sports clients and the chief executive officer of Bob Woolf Associates.

To the end, Woolf retained a reputation for honesty and cordiality, a rare combination in a cutthroat business in which agents fight for clients and against management, and sometimes care more for their percentage than for the athletes they represent.

He became friendly with many clients. Bird lived next door and called Woolf a “father figure.” Jim Plunkett lived in his basement.

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

Woolf had a knack for publicity. Before the sixth game of the 1986 American League playoffs between Boston and California, he showed up with Doug Flutie at Fenway Park to talk about the quarterback’s new deal with the Chicago Bears.

He was criticized for stealing the baseball stage. Vataha said Woolf appeared as a favor to a television station whose only camera crew was at Fenway. Woolf handled the knocks with style, knowing that publicity and name-dropping were good for business.

“Most people don’t know Bob Woolf,” said Wilson. “He was just a precious, precious, precious person.”

Competitors praised him.

Blank, 33, said “as I got going in my business, I would call him for advice and visit him in his office and he was always helpful.”

“Whenever you were in competition with Bob, it would be a fair game,” said agent Ron Grinker.

Negotiating adversaries admired him.

“I never met a more honest person,” said Red Sox executive vice president Lou Gorman.

The title of one of Woolf’s two books, “Friendly Persuasion,” described his negotiating style.

“I’m not out to break owners,” Woolf once said. “All athletes should do is participate in the growth industry.”

Julius Erving and others left him for refusing to renegotiate contracts.

But he also fought fiercely, without losing his temper, for his clients. His firm has about 200 of them. It handles all the financial affairs of some.

Woolf was shrewd and creative. There were few impasses, only temporary obstacles that a smile and a mood change could overcome.

“He never considered the other person an opponent,” Leone said. “He was thinking about them as working together.”

Once he was meeting in his office with then-owner Jonathan Kovler of the Chicago Bulls about Bill Cartwright’s contract. Kovler was getting upset. So about 4 p.m., Woolf invited Kovler to his Cape Cod home.

“By 7 o’clock at night, he and Jonathan were out on rubber rafts on a pond and that just changed the atmosphere,” Leone said. “They laughed and got the contract done on rubber rafts. Bob had thought, ‘What do I need to do to get a new rapport?’

“It was the cutest little sight to see the two of them, their arms hanging off the rafts.”

Woolf was different from other agents. He was the first and one of the best.

He would remind reporters, whose calls he always returned, that he wanted to be identified as an attorney.

“Without him, there would be no sports law,” said Harvard Law School professor Alan Dershowitz. “As my mother would say, he was a mensch. He created a business out of decency.”

Yet he could be self-effacing despite his huge influence.

So it was that last Monday afternoon, on the clay courts at David Park just outside Miami, he was amazed at how well he and Leone were playing.

She recalled his reaction: “He said, ‘This isn’t you, this isn’t me. Who are these people playing?’ ”

His amazement at his own success never left him, whether it was his tennis game or his rise from a spot above a sandwich shop to the top of a profession he created.