The John Dukakis Interview
By:
Michael D. McClellan | Wednesday, October 12th 2005
Watershed moments in sports often occur
without warning, athletic tsunamis that alternately
freeze time and forever redirect the course of the games
in which we so passionately involve ourselves. Babe
Ruth points toward Wrigley Field’s center field wall,
and the ensuing home run lifts pugilistic bravado from
the blood-soaked rings of South Philly and places it
squarely in the lap of mainstream America. Johnny
Unitas forces overtime in the 1958 NFL Championship
Game, then drives his team 80 yards for the winning
score, and the Golden Age of football is born. Michael
Jordan defies gravity, pulls back an automatic dunk to
lay the ball in the basket on the other side of the
rim, and we are instantly reminded why untold
millions want to Be Like Mike.
And then there are other turning points,
historically profound and yet far less celebrated, that
leave their own indelible impact upon the world of
sport. The introduction of the twenty-four second shot
clock, the designated hitter, sudden death overtime –
few stop to ponder what the games were like before the
advent of these devices, and yet each has thrilled us in
ways previously unimaginable. Such oversight is often
the case when it comes to the late Bob Woolf, the sports
agent pioneer who helped pave the way for the
lottery-sized contracts that professional athletes enjoy
today. From unfettered free agency to Jerry McGuire
to the globalization of the sports celebrity, Woolf’s
imprint can be felt at every turn, even if his
contributions remain forever outshone by clients such as
the legendary Larry Bird.
Woolf began his career in 1952 as a New
England attorney with a reputation for fairness and
decency. He was also a baseball fan, often attending
games at Fenway Park, this well before the advent of
player unions, arbitration, and collective bargaining
agreements. But even then he could sense that the
professional sporting world was about to explode in
dramatic and previously unimaginable ways. Television
had overtaken radio, and sports stars such as Ted
Williams and Hank Aaron were suddenly performing in
homes all across the country. In 1962, 10 years after
he began practicing law, Woolf fell into some work for
an obscure Boston Red Sox pitcher named Earl Wilson.
Wilson referred several of the city's athletes to him,
and pretty soon the attorney's practice also included
negotiating the contracts and finances of 9 out of 12
members of Bill Russell's legendary Boston Celtics.
Later came actors, entertainers, media personalities,
eventually even politicians. Woolf traveled with
Michael Dukakis during the Massachusetts governor’s
failed 1988 presidential campaign, and only Woolf's
adept and creative last-second negotiation with Ted
Koppel, Roone Arledge, and the Dukakis team saved the
candidate's opportunity to do a "Nightline" interview
one-on-one with the host. (Well, it seemed like a good
idea at the time.)
Woolf’s relationship with Dukakis led to the
hiring of Dukakis’ son, John, an aspiring actor who ran
the music business for Woolf and developed the local act
New Kids on the Block. The worldwide success of
Kids, in turn, prompted Woolf to open a Los
Angeles office, with the younger Dukakis in charge of
entertainment management. For Dukakis, the career move
was perfect timing. His deft management touch raised
the star power of two other high-profile acts, Boyz
II Men and Marky Mark & the Funky Bunch, and
further burnished his reputation as an astute judge of
talent.
If the professional synergy that existed
between Woolf and Dukakis is easy to understand, the
personal rapport between the two was fueled by, among
other things, deep New England roots and a passion for
the Boston Celtics. The same, however, could not be
said for the relationship between Woolf and the
legendary Red Auerbach. Auerbach had a long and genuine
dislike for Woolf, dating back to the Celtics’ glory
days of the 1960s, and then extending a decade later
when Woolf represented team captain John Havlicek. The
animosity reached a crescendo when a group of Terre
Haute businessmen selected Woolf to represent Larry Bird
in rookie contract negotiations. Auerbach berated and
belittled Woolf at every turn. There were times when
even Bird was astounded at Auerbach’s behavior. Woolf,
for his part, stood his ground. He understood
Auerbach’s old-school psychology, and had been around
the Boston sports scene long enough to know that when
Auerbach had taken over as coach in 1950, all contract
negotiations had occurred directly with the cigar
smoking patriarch of the Boston Celtics. And it had
been that way through much of his 16 seasons as coach:
Celtic great Frank Ramsey agreed to his first contract
with the Celtics in the Red Sox dugout at Fenway Park;
Tommy Heinsohn had talked contract with Auerbach as the
men stood side-by-side in the Boston Garden locker room,
pissing in the urinal and batting numbers back-and-forth
with hardly a care in the world. Woolf, of course, came
along and changed all of that. Auerbach viewed all
agents as poison, and the fact that Woolf once
represented 9 of his 12 players made him Public Enemy
No. 1.
Business associates and close friends, Woolf and Dukakis
would work together for four years, until John left to
become the general manager of Paisley Park Records, a
joint venture between the artist Prince and Warner Bros.
Records. The year was 1993, this at a time when Prince
was feuding with Warner Bros., and Prince had decided to
open an office in Centure City, California. Dukakis
served as the top executive until the office closed its
doors 12 months later – during his tenure, the company
released a Prince album as well as projects from George
Clinton and Mavis Staples.
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