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Douglass began practicing law with Caldwell, Parker, Foster
& Wigginton, the biggest law firm in Tallahassee. Douglass
developed a strong following, eventually deciding to form his
own firm, which would grow to as many nine lawyers.
Many of the friendships heʼd made while at UF would
impact his career, most notably with the late Lawton Chiles
(JD 55). The two met while undergraduate students at UF and
got to know each other through their service in ROTC, student
politics and as leaders in their fraternities. Douglass also
knew the woman who would become his friendʼs wife, Rhea
Chiles—both were on the staffs of the Alligator newspaper
and the Seminole yearbook.
Douglass and Chiles both served in Korea and graduated from
UF Law just months apart in 1955. When Chiles first ran for the
U.S. Senate in 1971, Douglass had little hesitation in deciding
to cut back on his own
practice to work on his
friendʼs campaign. While
Chiles served 18 years
in the Senate, Douglass
continued to make his
mark as a lawyer.
REPRESENTING
EVERYONE
The cases he took on
earned him selections in three categories in the book Best Lawyers
in America—personal injury plaintiff, commercial litigation and
criminal defense. Douglass developed a reputation as a lawyer
who would fight successfully for clients of all walks of life and all
races. He won verdicts to improve the minority hiring practices of
companies and schools and represented numerous indigent clients
pro bono in criminal cases. In 1989 Douglass and his partner
Thomas Powell won the acquittal of a rural black family accused
of killing three white attackers.
He also won numerous multimillion-dollar settlements
for individuals in personal injury cases, including a 1981
settlement for $5.5 million—from an all-white jury—that
was then the nationʼs largest amount ever awarded to a black
plaintiff. The man, who had been crushed between his truck
and a trailer while loading in a limestone mine near Perry, Fla.,
wasnʼt killed, but his life, and that of his wife, had been ruined.
For Douglass, the victory was particularly satisfying because
he thought the defendants were trying to take advantage of the
man because he was black. The verdict included $1.05 million
for the manʼs wife for loss of consortium.
“For black people that was just totally unheard of. They were
good people and they were badly damaged,” Douglass explains.
“Iʼve enjoyed representing the underdog from time to time. And
Iʼve enjoyed representing the upper dog occasionally because they
pay well. My philosophyʼs more attuned to being a Democrat.”
Those Democratic ties would come up again in 1995, when
Chiles called on his good friend as the state took on tobacco
companies. Though Douglass declined the invitation to get
involved on the trial team for Floridaʼs lawsuit against tobacco
companies in the 1990s, he did take on the supervisory power
for the governor over the litigation challenging the statute. When
Publix, Associated Industries and other special interest groups
brought suit to declare that statute unconstitutional, Douglass
argued successfully for the constitutionality of the statute in
circuit court, eventually winning a 4-3 decision by the Florida
Supreme Court.
When Chiles died during his final month in office in 1998,
Douglass immediately went to the Governorʼs Mansion to try
to help, answering questions from the press and shedding tears
with old friends.
Shortly afterward, Douglass went back into full-time
practice, trying a case on behalf of a woman who was suing
her insurance company, which had refused to settle within
the limits of the her $300,000 underinsured motorist policy.
Convinced the woman was faking her injuries, the insurance
company put her under
surveillance, a move
“I got to Munson and we had
the only electricity and
running water within 15
to 20 miles of where we lived.”
that backfired when
the jury saw the tapes.
The insurance company
offered the woman
$50,000. The juryʼs
verdict was $1.3 million.
It was settled with the
insurer for a figure much
higher than her policy
limits because of the companyʼs bad faith in refusing to settle
before trial.
“So I felt like it was time for me to sort of slack off for a little
bit,” Douglass said.
THE HONORS COME
His “duty and service to the public” was honored last year
when The Florida Bar Foundation recognized Douglass with its
annual Medal of Honor. Considered the stateʼs most prestigious
award for attorneys, the Medal of Honor has been bestowed in
the past to former Gov. Reubin Askew (JD 56), former U.S.
Attorney General Janet Reno, ABA Presidents Chesterfield
Smith (JD 48) and Martha Barnett (JD 73), Attorney General
Richard Ervin (JD 28), Robert M. Ervin (JD 47), and other
luminaries of the Bar.
Today, Douglass spends much of his time mediating cases,
along with working some appeals related to constitutional law;
and occasionally consulting with lawyers on trials.
He and his wife Terese live on a farm northeast of Tallahassee,
where Douglass still gets up at 5 a.m. every day and looks after
a few cows. After open-heart surgery a while back, he began
walking every morning and now works out at the gym in an
effort, he says, to “stay in shape for an old man.”
Every Monday, as the noon hour approaches, on a day like
the one that brings these buddies to the Seineyard Restaurant,
you can find Douglass waiting for his old friend Tom Barkdull
to pick him up for lunch.
“I get along pretty good,” he says. “Iʼm doing what most
old lawyers do. Still coming to the office everyday and having a
practice of sorts and keeping active in what I love to do.” ■
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