When Dexter Douglass was fresh out of the University of Florida law school 58 years ago, one of his first cases was a petty gambling charge against a client who had been caught red-handed.
Tallahassee police were raiding a bolita joint when Martin Van Buren Tanner, the butler to 11 Florida governors, walked in the door with a play slip in one fist and $2.60 in the other.
Douglass convinced a city judge that the raid had been an illegal search and to dismiss the charge.
Thousands of cases later, Douglass lost the greatest one he helped litigate: Al Gore's challenge to the Florida vote count that made George W. Bush president.
Many people believe, however, that had Gore followed the strategic advice of his canny Florida "country lawyer," he would have won. Demand a statewide recount, Douglass urged.
But Gore let his higher-priced New York lead counsel persuade him to target only counties where the Democratic vote had been strong and enough ballots had been rejected to make a difference.
As he saw his chances evaporating before the U.S. Supreme Court, Gore telephoned then-Sen. Bob Graham, the Florida Democrat.
"I think we've made a mistake," he said.
"There is no way to know if things would have been different," says Barry Richard, Bush's lead counsel in the historic case. "We do know that they could not have been worse for Gore. We also know that Dexter was a very smart guy."
No one who ever met Douglass would disagree. He was also a most entertaining, unpretentious likable guy.
His death last Tuesday of cancer at the age of 83 was mourned statewide.
To have known him in many capacities — defense lawyer, general counsel to Gov. Lawton Chiles, chair of a successful Constitution Revision Commission, and raconteur who would keep you lingering long after the plates had been cleared — was an unforgettable pleasure.
Among the clients he defended successfully was a Florida Supreme Court justice who faced impeachment because of articles I wrote and a state comptroller who seemed to give the newspaper credit we didn't deserve for the income tax indictment he was fighting.
With Douglass, however, it wasn't personal. At a Florida Bar luncheon where another lawyer and close friend disputed my account of the Supreme Court scandal, Dexter stood up to say I had gotten it just right.
Although he lost two races for elected office, few people have left so many enduring marks on their state.
The Florida Bar Foundation recognized those accomplishments in 2006 with its Medal of Honor Award. The citation noted that, among other things, he had chaired the trustees of the Florida School for the Deaf and Blind for 16 years, desegregating it without a hint of the anger and strife seen elsewhere.
"With warmth, charm and the twinkle in his eye, Dexter Douglass has gained the respect and admiration of allies and adversaries alike," the citation said.
As top lawyer to Chiles, his law school classmate and lifelong friend, Douglass conducted the legal strategy (including passing a stealth bill through the Legislature) that led to Florida winning a precedent-setting $13 billion settlement from the tobacco industry.
When Chiles appointed him chairman of the Constitution Revision Commission in 1997-98, he put to good use the lesson of his service on the first one 20 years earlier: If there isn't a substantial majority of members for a proposal, the voters aren't likely to ratify it.
His insistence on supermajority votes to put anything on the ballot led to success for dramatic reforms that had eluded decades of effort, including shrinking the elected Cabinet from six members to three, creation of a unified wildlife agency, improved funding for the courts and a requirement for a "uniform" public school system that the Florida Supreme Court interpreted to ban private school vouchers.
His biggest disappointment was the commission's rejection, due to the supermajority rule, of independent legislative redistricting. There were enough votes until intense pressure from Republican legislators peeled several away.
He flashed no anger in public. But he found out what one of the defectors, a lobbyist, wanted most during the next session of the Legislature. Then ne made sure Chiles vetoed it.
Douglass' effort wasn't for naught. The anti-gerrymandering standards survive in two constitutional amendments voters approved in 2010.
Martin Dyckman, a retired associate editor of the Tampa Bay Times, is author of Reubin O'D. Askew and the Golden Age of Florida Politics, published by the University Press of Florida.