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Woolf, Robert (Bob) (1994)

Writer: Maine Baseball HOF
Maine Baseball HOF
Aug 8, 2019
3 min read

Bob Woolf 1990

When he died suddenly on November 30, 1993, Bob Woolf, 65, was nationally and internationally recognized for negotiating more than 2,000 contracts in the field of sports and entertainment.

A pioneer in the role of sports agent, Woolf was also the author of two books, “Behind Closed Doors" and “Friendly Persuasion".

Named one of the 100 Most Powerful and Influential Attorneys in America by the National Law Journal and one of the 100 Most Powerful People in Sports by the Sporting News, Woolf's experiences took him from weekends with Prince Charles and Prince Rainier to informal meetings with Mikhail Gorbachev and collaborative efforts with Armand Hammer.

Yet, for ell his high-profile activities, Woolf never forgot his roots on Munjoy Hill in Portland.

On a visit to his home city to receive an award from the Alumni Association of the Boys and Girls Club of America, he visited the local club on Cumberland Avenue.

The club has photographs taken that day of Woolf shooting baskets with children.

Woolf was a dues-paying member of the association and a generous contributor.


Humble about his success, Woolf seemed genuinely surprised by what he had achieved.

"Who would've thought a kid from Munjoy Hill could be sitting here, saying this," said Woolf during an interview when he was in Portland.

The first major league baseball player represented by Woolf was Earl Wilson, who pitched a no-hit game for the Red Sox in 1962.

Hie subsequently represented baseball players Luis Tiant, Carl Yastrzemski, Ken Harrelson, Thurman Munson, Bob Stanley and Mark Fidrych.

Also basketball players Larry Bird, John Havlicek, Julius Erving, Dominique Wilkins and Robert Parish.

Also football players Raghib “Rocket* Ismail, Jim Plunkett, Dexter Manley and Mike Buck, the former UMaine quarterback until recently with the New Orleans Saints.

Some athletes, including Erving, fired Woolf for his refusal to re-negotiate for more money in the middle of their contracts.

"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.


"He really was a lover of sports, as opposed to simply using it to gain his livelihood.

The son of Jewish immigrants, Woolf attended Boston College on a basketball scholarship. He earned his law degree at Boston University.

Woolf, however, never forgot delivering newspapers up and down Congress Street in his native city or walking to the (then) Boys Club or Setting pins.

In his book "Behind Closed Doors," Woolf said this about Portland, where he grew up in the 1940's: “This is the kind of small, dry, unhurried town so basic to the heritage of Maine, the kind that is so ripe for jokes.

But I loved it, and still do, and go back as often as I can, maybe six or seven times a year.

It helps cleanse my mind of the latest crisis or legal tangle involving one of my athletes.”

"There is something encouraging about a place that never changes, where the air and the streams are still pure and no one forces himself on you. There is, always will be, a lot of Portland in me."



Earl Wilson_Woolf's first player




https://www.youtube.com/watch?v=WyNJBar4K9c


From Fold 3 Legacy pages




Yaz 1969 Topps all star

One of his first major clients was Yastrzemski, the Red Sox slugger, who also became a close and generous friend. When he retired, Yastrzemski gave Mr. Woolf a wealth of his personal baseball memorabilia, which Mr. Woolf displayed proudly in his office on what became known as the Yaz wall. Office Overlooks Fenway Park


It was no accident that Mr. Woolf's office in the John Hancock building overlooked Fenway Park. Visitors who wondered whether the sports agent was a true sports fan had only to take a look through the telescope at his office window to find out: It was permanently aimed and focused on the Fenway mound and batter's box.


As his fame spread and his client list grew, Mr. Woolf, who estimated that he had negotiated more than 20,000 contracts by 1992, grew increasingly concerned by the spendthrift ways of young clients who didn't know the value of a million dollars.


Accordingly he often insisted on becoming the personal manager of the players he represented, overseeing their investments to make sure they would live comfortably after their peak earning years. He even went so far as to put his clients on allowances, or tried to. First-Class Allowance




Behind Closed Doors .1977

"Professional ethics would never permit Woolf to say, “No, that's too much,” to some club owner's offers, yet he is not out after the employer's last dime or even his last dollar. “I like to leave something on the table for the other guy,” he says. “I feel we're all in this together. I want the owner to make a profit and I feel strongly that he must have some protection for his investment. It's important to all of us that the game prospers.”


Woolf, Robert (Bob) (94) MEBBHOF



Boat Ramp At East End, Portland, Maine - Aerial Photograph Wall Art By: Dave Cleaveland

 
 
 

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Meet the 2026 Maine Baseball Hall of Fame inductees
Portland Press Herald 4/10/2026
https://www.pressherald.com/2026/04/10/meet-the-2026-maine-baseball-hall-of-fame-inductees/?copylink=true

 

Former St. Dominic and current Gray-New Gloucester coach Bob Blackman and Cony coach Don Plourde are among the 11 members of the newest class. Four coaches currently preparing for the upcoming high school baseball season are among the 11 inductees in the 2026 Maine Baseball Hall of Fame class.

Gray-New Gloucester’s Bob Blackman, Brewer’s Dana Corey, Hampden Academy’s Jon Perry and Cony’s Don Plourde are all part of the class that will be inducted on Oct. 4 at the Holiday Inn by the Bay in Portland. Blackman coached St. Dominic High School to nine state championships in 22 seasons before the school closed at the end of the last school year. He was named the coach at Gray-New Gloucester in September. Corey hit .359 at the University of Maine in 1971. He played two seasons in the Chicago Cubs system and has been the head coach at Brewer for 18 seasons.

Perry hit .381 at the University of Maine in 1981 and helped the Black Bears reach the College World Series. He has coached for the past 45 seasons at the high school, American Legion and collegiate levels. 

Plourde is in his 17th season as the coach at Cony High School and has been named the KVAC Coach of the Year five times. He has been coaching at various levels for more than 30 years. 

Others earning induction are: 

Al Cloutier, who has been involved in baseball in Augusta as a player, Cony High and American Legion coach, Babe Ruth League director and volunteer. 

John Kolasinski, who was a college coach at for 37 years, first at Husson and later at Siena Heights University in Michigan. He is a five-time New England Coach of the Year winner.

Mark Littlefield, a Portland High graduate, who is now in his 36th season working on the medical staff of the New York Yankees organization. 

Scott Littlefield, a Portland High graduate, who will be inducted posthumously. Littlefield coached at Florida State University and the University of Southern Maine before working for 34 years as a Major League Baseball scout, including 16 as a player personnel special assistant for the Texas Rangers.

J. Ronald Livington, who will be inducted posthumously. Livingston was an All-Star infielder for the semi-pro Presque Isle Indians in the Northern Aroostook League in the 1930 and 1940s. He also coached and was a director in the South Portland National Little League.

Mike McCullum, of Portland, who hit .338 at the University of Southern Maine and earned ABCA Division III All-American honors in 1999. 

Jim Taylor of Lewiston, who was a founding member of the Central Maine Board of Approved Baseball Umpires and was instrumental in starting the Maine chapter of the Collegiate Baseball Umpires Association.

Maine Baseball Hall of Fame day  Delta Dental Park aka Hadlock Field 7/19/2026
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