With a ready humor that served him as well at work as it did in his highly competitive family, William E. Bailey, shown in his Beacon Street office, also hosted the nationally syndicated radio talk show “It’s Your Money.’’
(Globe Photo/ File 1982)
William E. Bailey, at 68; was a top spokesman for the insurance industry
With a ready humor that served him as well at work as it did in his highly competitive family, William E. Bailey, shown in his Beacon Street office, also hosted the nationally syndicated radio talk show “It’s Your Money.’’
(Globe Photo/ File 1982)
Prescient amid a swirl of asbestos lawsuits, William E. Bailey contemplated a complex future in September 1982 as he sat in his Beacon Street office, where he was senior vice president of Commercial Union Insurance of Boston. Weeks earlier, he had told a government panel that the issues at hand went beyond settling claims against his company’s client.
“It is, rather, the broader question of how we, as a nation, will deal in the future with what can already be predicted as a vast array of environmental and occupational disease claims,’’ he told the committee of lawmakers. “The prospects, based upon past experience, are not encouraging.’’
In the years since, his prediction was borne out through enough headline-grabbing legal actions to fill courtrooms around the world with plaintiffs and lawyers.
Dr. Bailey, meanwhile, became a top spokesman for the US insurance industry and a point man at the site of natural disasters from Hurricane Andrew in 1992 to Hurricane Katrina in 2005.
With ready humor that served him as well at work as it did in his highly competitive family, he also hosted the nationally syndicated radio talk show “It’s Your Money.’’
Dr. Bailey died Aug. 21 in Kaplan Family Hospice House in Danvers of cancer. He was 68 and lived in Chelsea.
The younger brother of famed trial attorney F. Lee Bailey, his path followed deep footsteps through Harvard Law School and into Boston’s legal community.
No softer a shadow was cast by Dr. Bailey’s mother, Grace L. Mitchell, a pioneering day-care provider who received a master’s degree at the same Harvard commencement when he graduated with a bachelor’s.
“For most people, it would probably be terribly difficult to grow up and practice law in the shadow of such a renowned lawyer and brother as F. Lee Bailey,’’ said Kenneth Fishman, an associate justice of the state Superior Court who has known Dr. Bailey since 1975. “But Bill was remarkable. His intellect and perception enabled him to find his own special niche in the legal world. He always seemed one step ahead of the industry in terms of recognizing the kinds of issues they were going to have deal with.’’
Staying a step ahead in his immediate family was another matter, however.
“In the Bailey family, you had to be a real hard charger, and he certainly found a way to do it,’’ Fishman said of Dr. Bailey. “The competition in the outside world was one thing, but the competition in the Bailey family was something else, from the mother on down.’’
Dr. Bailey’s good nature carried him through in family gatherings where his accomplished brother and mother could be scene-stealers. Indeed, she saw his pleasantness as a defining difference between her two sons.
“If you met Bill at a cocktail party he would talk your head off and ask you all kinds of things about yourself,’’ Mitchell told the Sun-Sentinel of Fort Lauderdale, Fla., in 1992. “Maybe you would tell him you were worried about your Aunt Suzy. Five years later, you could run into Bill in Times Square and the first thing he would ask you would be, ‘How’s your Aunt Suzy?’ You could meet Lee today and he’d be gracious and charming, but you could meet him in the street the next day and he’d look right through you.’’
Born in Newton, William Edward Bailey graduated from Belmont Hill School in Belmont, then went to Harvard.
After graduating in 1962, he served with the Marines for three years and rose to captain.
“He had an extraordinary amount of charm for a guy who basically was no pushover,’’ his brother said of Dr. Bailey, who had been a Marine platoon leader.
Dr. Bailey returned home to attend Harvard Law School, where he was among the early students taught by Alan M. Dershowitz, his brother said.
Graduating in 1968, Dr. Bailey went to work at Hale & Dorr in Boston, where he was a trial assistant to James D. St. Clair, who later represented President Nixon during impeachment proceedings initiated as part of the Watergate scandal.
“They outbid me for his services,’’ said his brother, who finally lured Dr. Bailey to his own firm in 1970. “I tried to get him right out of law school, but they offered him more money.’’
Dr. Bailey practiced with his brother until 1977, when he went to work at Commercial Union Insurance.
He also received a chartered property casualty underwriter designation, and became a special counsel to Insurance Information Institute in 1986.
Based on his experience directing the Hurricane Insurance Information Center in Florida after Hurricane Andrew struck, he returned to college, writing a doctoral dissertation on the disaster’s impact on the insurance market.
He received a doctorate in 1996 from Union Institute, based in Cincinnati.
In June 1970, he married Irene LaCentra, who is known as Rene - his “first and only’’ wife, he noted in the 25th anniversary report of his Harvard class.
“Life is good,’’ he wrote in the report. “The law has been a generous benefactor.’’
Nevertheless, he didn’t hesitate to point out that the world had too many lawyers, often making jokes at his profession’s expense, like the one he told the Fort Lauderdale newspaper in 1992 about former Soviet leader Mikhail Gorbachev.
“Gorbachev was standing on the balustrade of the Kremlin at the annual May Day parade,’’ Dr. Bailey said. “First the soldiers marched by, then came the tanks, then the missiles. Then a flatbed truck came by, carrying these gentlemen wearing three-piece suits. One of Gorbachev’s lieutenants asked him what the men on the flatbed were there for. And Gorbachev said, ‘That’s my secret weapon. That’s a group of American trial lawyers. There’s no end to the destruction they can cause.’ ’’
Said Fishman: “Bill had a remarkable sense of humor, a warehouse of jokes, and an engaging and infectious laugh.’’
“The only thing in the claim business that amazes you is how sometimes the most unexpected things result and then we find ways to make them humorous when we tell stories about them,’’ he told the publication Odd Claims Focus in 1992. “The truth is that the humor is your way of finding relief from the pain, embarrassment, and tragedy you sense others must have suffered.’’
In addition to his wife and brother, Dr. Bailey leaves a sister, Nancy of Chelsea.
A memorial service will be held Sept. 26 at 11 a.m. in Trinity Church, the First Congregational Church in Waltham.![]()


