The John Dukakis Interview
By:
Michael D. McClellan | Wednesday, October 12th 2005
The late Bob Woolf was a pioneer in the business of
representing professional athletes. Please tell me a
little about Mr. Woolf – what qualities do you think
made him the most successful agent of his generation?
JOHN DUKAKIS
Bob was a smart guy, a very determined man. He figured
out that there was a need out there for professional
athletes to be properly represented. No one was doing
it. As a consequence, the team owners were making a lot
of money and they were paying players a tiny fraction of
the income that was generated. This was the case across
the board, from the players who weren’t considered
stars, to the players who made a difference in selling
the tickets and getting fans to watch on TV. So he
started to change that pattern very early in his
career. He was determined to make a difference. For
the most part, he stuck to team sports. He understood
how that worked, and he worked it very well. He was
aggressive at recruiting new clients, and he made a very
good case for why he was better than the rest. And
although Woolf & Associates got into other things later,
like dealing with entertainers, he stuck to his bread
and butter, which was representing professional athletes
on team sports. He didn’t get into other things, like
the Donald Dells and the Mark McCormacks, who got into
producing events. Bob really wasn’t interested in doing
that.
The late Vince Lombardi was quoted as saying that he'd
never met a sports agent that he liked. Yet the
legendary Red Auerbach, himself no fan of the agents
that emerged with the birth of free agency, seemed to
have a particular animosity toward Mr. Woolf. How was
Mr. Woolf able to overcome this and eventually win Red
over?
JOHN DUKAKIS
I think by always being fair. I think what Bob was able
to do was put his integrity out there for everyone to
see. He was an honest broker, and over time that really
made a difference in the way some of the old guard,
including Red, came to view his practice. Red knew that
if there were problems he could always deal with Bob.
He may have had to pay a little more money than he had
wanted to, but he knew that there was some stability
with his players – they were less likely to move to
another team, because Bob would do his best to get the
best deal with the Celtics first.
Obviously, Vince Lombardi saw sports agents in his era
as sharks who were out to make his life miserable. Red
may have felt the same way to some degree. I don’t
think it’s a secret that Red liked negotiating directly
with the players, which he had done successfully for
many years, but he also understood that times were
changing in that regard. Sports agents may not have
made much sense to him, but the reality is that they
perform a service, and most of the good ones out there
perform a service that’s beneficial for their clients,
and for their team as well.
In 1989, Mr. Woolf noted that the agent profession “went
from zero competition to an industry in which everyone
with a telephone could find a niche”. How was Mr. Woolf
able to stay ahead of the curve and build one of the
most recognizable identities in the business?
JOHN DUKAKIS
It’s funny that you mention that, because that’s the
year that I started working for him. And he was right
to make that statement – as the money got bigger and the
contracts got larger and more lucrative, everyone wanted
to jump into the business of representing professional
athletes.
I’ve been in the entertainment business now for a long
time, and there are certain professions where people out
there think, ‘Well, I can do that.’ I think that there
are couple of things that can happen when the barriers
to enter a profession are lowered. One thing is that it
dissipates the whole profession and makes everybody look
bad. The other thing is that those who provide a real
service and have a good reputation for getting the job
done tend to tower above the rest. I think that Bob, by
reputation, made it clear to people that he wasn’t like
the rest. And even when I joined him, there were only a
handful of guys out there who really did it the right
way. Bob was definitely one of them.
Mr. Woolf also had a special relationship with his most
prominent client – the great Larry Bird. On the surface
they seemed to be the sport world's version of the Odd
Couple, Oscar and Felix if you will. But Mr. Woolf was
more down-to-earth than people might imagine, and Larry
was anything but a country bumpkin. Was this purely a
business relationship, or did it extend beyond numbers
on a contract?
JOHN DUKAKIS
I think there was a great deal of affection between the
two of them. I’m not sure that they spent a lot of time
together socially, but I think that had more to do with
the fact that Larry is a very private guy. He’s still
someone who sticks to what he really wants to do, and at
the time that was playing basketball and raising a
family. I think that Bob really respected Larry’s
privacy. But it was definitely a warm and affectionate
relationship, with very little tension. There were
other people in our office involved with Larry who
provided a service and tried to deflect some of the
distractions away from him. Things like requests for
autographed balls and speaking requests went through our
office. I think that lifted a little bit of a burden
from Larry.
Mr. Woolf began representing Larry Bird after a series
of meetings set up by a committee of Terre Haute
businessmen who "adopted" Bird, and advised him on his
finances. They reduced a list of three final candidates
to one after an eight-hour session. Knowing him as you
did, what does this say about Mr. Woolf?
JOHN DUKAKIS
Clearly that he was in the top tier. I think it had to
do with Bob’s ability, in a room, to make you feel like
you were the only person who mattered. I also think
there was a little bit of a father-thing going on,
because Larry had lost his father at a young age. And
then there was that all-importance comfort level.
Everyone seeks out a certain comfort level when they are
entering into any kind of business relationship. I
don’t know for sure, but I think Larry and his team
narrowed it down to those three candidates through some
sort of dollar formula, and then it became less about
money and more about things on a very personal level.
With Larry being drafted by the Celtics, the fact that
Bob’s roots were so imbedded in Boston helped a great
deal. He was very much a part of the fabric of that
city. In addition to being a national figure in his
profession, he was clearly identified with that
relationship to Boston – from his accent, to the food he
ate, to where he grew up as a child. And as aside, Bob
came from very humble beginnings. He wasn’t a farm boy,
but every amount of success that he ever got had to do
with him and his character. I think Larry could really
identify with that part of Bob’s makeup.
The movie Jerry McGuire seems to sum up the big
business of sport in one tagline: "Show me the money."
While that may broadly be the case – controversial agent
Drew Rosenhaus comes to mind – it seems as if Mr. Woolf
was concerned about more than just dollars and cents.
Is this an accurate assessment?
JOHN DUKAKIS
The money was obviously important, but Bob was also
about longevity. He wanted to do the job he loved for a
long time, and he wanted to be associated with people
who were going to be around for awhile. And Bob really
did enjoy his profession. He loved being in the
limelight. He loved being associated with great,
brilliant athletes. So I think he found it very
fulfilling. And he really enjoyed helping these
athletes develop their skills outside of sports.
Whether it was simply planning for their financial
future – a lot of these guys were getting money for the
very first time – or whether it was developing a career
after sports, Bob had a lot of experience in helping
athletes succeed over the long term. He really enjoyed
that aspect of his job.
Your father is former Massachusetts governor Michael
Dukakis. Mr. Woolf was involved in his 1988 bid to
become president. How did these two great men meet, and
what was their relationship like?
JOHN DUKAKIS
Bob lived in our hometown of Brookline, Massachusetts.
Growing up, I had certainly heard of him because I read
the sports pages. Over the years the two of them may
have spent some time doing some political things
together, but I’m not sure how close that relationship
was. I knew it grew a great deal in ’88, when Bob was
able to bring Joe Montana and some other prominent
athletes in to work on the campaign. I believe Bob was
also involved in raising money in that campaign as well.
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