Attorney William Dexter Douglass, who died Tuesday, gained fame in Tallahassee as an adviser to governors, a leader in Florida’s fight against Big Tobacco and chief counsel to Vice President Al Gore during the controversial 2000 election recount in Florida.
His roots run deep in Okaloosa County.
The Douglass family was among the first to settle here, Dexter Douglass was raised in Crestview, where his mother ran a popular restaurant called The Grill and his father attained radio celebrity as a newsman called “Cooter.”
“Every morning my family started the day with Cooter Douglass and the news,” said attorney Jerry Miller, who grew up in Fort Walton Beach in a time before television.
Dexter Douglass grew up around the radio industry and Jerry Milligan, a former Crestview mayor with ties to radio himself, recalled Dexter sometimes filling in for his father to cover an afternoon news slot.
Douglass left the area to attend law school at the University of Florida. There he met and befriended Lawton Chiles, another man with big ambitions and a strong connection to Northwest Florida.
Douglass joined one of the most prestigious law firms in Tallahassee after graduation and eventually opened a practice of his own.
Niceville attorney Stanley Bruce Powell said he knew when he went to Florida State University to law school that Douglass shared his affinity for Okaloosa County.
“I knew he was from around here because his father ran that radio station,” Powell said.
Powell used his Northwest Florida connection to wrangle an internship and spent five years after graduation as a law partner in Douglass’ firm.
“He was one fine lawyer,” Powell said. “He was my mentor, or, like I used to call him, my tor-mentor.”
“A stickler for excellence,” Douglass “was in my mind one of the last really great lawyers,” Powell added.
To this day Powell keeps a document he once prepared for Douglass that was returned to him with “this is ridiculous” scratched across it.
“I show it to some of my associates and say, ‘Ya’ll think I’m a tough boss?’ ”
When his old friend Chiles became governor, Douglass secured a job as general counsel. From there he teamed with Pensacola attorney Fred Levin to take on Big Tobacco.
The squadron of lawyers they assembled scored a landmark $13 billion settlement in 1999.
“I suggested the procedure about going out to get Big Tobacco and Gov. Chiles said, ‘Let’s do it,’ ” Levin recalled. “He had me get with his friend and plan out step by step how to do this. Dexter advised Chiles every step of the way.
“He was a fine gentleman, a great lawyer and a class act,” Levin said of Douglass.
However, Douglass’ close association with Chiles didn’t pay off for him when the tobacco settlement finally was reached.
To prevent the perception of a conflict of interest Chiles forbade Douglass from sharing in the exorbitant legal fees that came with the huge award from the tobacco industry, Levin said.
He said the settlement money was split up in Washington, D.C., on a Friday and Chiles died the next day.
“I always wondered whether the governor regretted that decision,” he said.
Douglass grabbed national headlines in 2000 when he was named lead counsel in Florida for Al Gore as the disputed results of the 2000 presidential election were litigated.
His demeanor in court was such that a New York Times reporter chose to refer to him as “a stem-winding old-school Tallahassee orator who in another era would have worn a white suit and a pocket watch to court.”
Douglass, who died Tuesday morning at the age of 83, was celebrated in several obituaries written about him as a lawyer willing to take cases big or small and work pro bono if need be.
Milligan got to know Douglass first as a young attorney representing his by then widowed mother in matters pertaining to WDSP radio in DeFuniak Springs. Cooter Douglass had bought the station two years before he died.
“He was an outstanding gentleman,” Milligan said of the younger Douglass.
Milligan also saw the cagey lawyer side of Douglass when, while he was mayor, Crestview got into a dispute with Okaloosa County over the rights to provide water service to the Countryview Estatessubdivision.
Douglass was hired by the subdivision’s developer, who was on the city’s side in the dispute, Milligan said.
As the two sides bickered, a county public works director who was a former lieutenant colonel sent road graders to the subdivision to block city engineers from their water line project.
From then on, Douglass referred to the public works director as colonel, a title the county official clearly didn’t like.
“He knew when to stick the needle in at just the right time,” Milligan recalled.
Miller, who now serves as the city attorney for Crestview, recalled Dexter Douglass as someone his parents would hold out as an example to him.
“He was an element of pride for the county,” he said.
“We had such a small community back then,” Miller added. “People were held up to us as models, to say if we did the right things we could do things in our lives.”
Contact Daily News Staff Writer Tom McLaughlin at 850-315-4435 or tmclaughlin@nwfdailynews.com. Follow him on Twitter @TomMnwfdn.