BRATTLEBORO—It wasn’t quite an Irish wake, since the guest of honor was still very much among the living.
But the Guinness and the stories flowed at the law office of Thomas Costello last Thursday as the friends and colleagues of Timothy O’Connor gathered to pay homage and to salute his 50 years of service as an attorney and public official in Brattleboro.
The 74-year-old O’Connor, who has worked as a lawyer in town since 1961, retired on April 1.
Aside from taking care of any pending cases, O’Connor turned over the practice to attorney Jim Maxwell, who will be leaving his office in the Hooker-Dunham building on Main Street and moving into O’Connor’s former office on 136 Western Ave.
O’Connor won’t totally leave the legal business. He said he will help Maxwell part-time.
Maxwell said he knows he has big shoes to fill in taking over O’Connor’s practice.
“You don’t take over for a legend,” he said. “You try to work hard and do the same good job that he did. Every lawyer is different, but the one thing that is paramount is the relationships with clients, and Tim was exemplary in that regard.”
A lifetime in a few blocks
The site for Tim O’Connor’s retirement party was a serendipitous junction of the big moments of his life.
Costello’s office is just up the hill from St. Michael’s School, from where O’Connor was graduated from high school, and from St. Michael’s Roman Catholic Church, where he married a girl from Putney named Martha Hannum nearly 50 years ago.
Before Costello hung his shingle on Putney Road, his office belonged to Edward John, the attorney who hired O’Connor out of Georgetown University’s Law School five decades ago.
“Eddie was in the front office, and Tim got the small office [in the back], and he became known to many around town as ‘the mole in the hole,’” said Costello.
The lawyers and judges who gathered at Costello’s were across the street from Windham District Court, and just a stone’s throw away from the Municipal Center, former site of the Brattleboro Municipal Court, over which O’Connor once presided.
And they stood just a few blocks away from Oak Street, the longtime home of Tim and Martha O’Connor.
“A whole lifetime in just a few blocks,” said former Vermont Superior Court Judge Arthur O’Dea, a classmate of O’Connor’s at Holy Cross and Georgetown Law School. “How many people can say that?”
“Before the age of computers, everything was done alphabetically, so that’s how we ended up as roommates,” he said. “Mass was at 7 a.m., and it was mandatory in those days [at Holy Cross], and the Jesuits checked you in.”
So, he said, “we established a custom where every other day, we checked each other in for Mass. We liked to sleep, so for three years, I would attend Mass one day, and Tim would attend on the other day.”
With that subterfuge, a lifelong friendship was born.
“When I moved up to Vermont from New Jersey in 1969, I could get into any door, because all I had to do was say I was friend of Timmy’s,” said O’Dea.
O’Connor was admitted to the Vermont Bar in 1961, and like many small-town lawyers, he started out as a generalist, doing everything from criminal cases to divorces to probate law. His colleagues praised O’Connor for his affable nature and his ability to reach agreements without being disagreeable.
The legal community in Brattleboro was a tight-knit one when O’Connor started out, said attorney Lawrin Crispe.
“It was a very congenial bar,” said Crispe. “We’d always got together. We’d used to have the docket calls, and judges would call us up to Newfane, and Timmy was always at the center of that. He tried to keep up the camaraderie in the interest of trying to maintain civility.
“My dad [Luke Crispe, a longtime attorney in Brattleboro] used to tell me that ‘Timmy is one guy you can rely on anytime you’ve got a problem. You always count on Tim O’Connor.’ Over 40 years, Tim has provided me with a lot of good pointers, a lot of good education.”
Crispe called O’Connor “the consummate country lawyer” and said he has set a great example for young lawyers in Brattleboro to follow in terms of “not only earning a decent living, but also doing a lot for his community at the same time, and doing a lot for his clients, which is evident by the loyalty that they show Tim.”
O’Connor eventually gave up criminal law to focus mainly on real estate, contracts, and wills. He also spent time on the other side of the bench, as the presiding judge in the former Brattleboro Municipal Court from 1964 to 1967. He said he gave up that job when the court went from meeting two mornings a week operating full time.
Vermont Superior Court John Wesley read a proclamation from his court honoring O’Connor.
Wesley remembered his days as a Legal Services lawyer in the 1970s, “when you weren’t necessarily immediately looked at as part of the group.” He said he knew he shed his outsider status when O’Connor offered him tickets to see his beloved Georgetown Hoyas play basketball in Boston.
“There are fraternities, and then there are fraternities,” said Wesley. “Getting into that fraternity, I knew that was a big step.”
Wesley said he learned a lot about practicing “not only real estate law, but community law, through Tim’s generosity.”
Under the golden dome
Besides his long legal career, O’Connor has served as town moderator and was elected six times to the Vermont House of Representatives, serving as House Speaker from 1975 to 1980.
Not only was O’Connor the first Democrat elected Speaker of the House, he was elected even though his party was in the minority throughout his tenure.
Costello, who served in the Legislature as a Democratic representative from Rutland during O’Connor’s tenure, remembers taking a trip to Boston and meeting the two most powerful figures in Massachusetts politics, House Speaker Thomas McGee and Senate President William Bulger.
“These are real tough guys, yet they genuflected before Tim and called him ‘The Miracle Man,’” said Costello.
Costello said Bulger and McGee couldn’t believe that a Democrat could get elected to lead a legislative body as a member of the minority party.
“That was something that was beyond their expectations,” he said.
O’Connor’s successor as House Speaker, Republican Stephan Morse of Newfane, said he learned very quickly as a young lawmaker how O’Connor pulled off a seemingly impossible political feat.
Watching him preside over the House, Morse said that “there was no bias.”
“It was all fair,” he said. “He was there to make sure the people’s work got done. To his credit, he made sure that people were getting along.”
Thomas P. Salmon’s tenure as governor of Vermont between 1973 and 1977 coincided with O’Connor’s rise to the speakership.
“On paper, there was no way that a Democrat would get elected Speaker,” Salmon said. “But it happened, my friends, for one reason, and one reason only — the Legislature of the state of Vermont had never met any person as fair, as decent, as thoughtful, as caring, as the member from Brattleboro.”
In 1980, O’Connor ran for the Democratic nomination for governor and Salmon said he received “90 percent of the vote in Windham County. Nine-O. That is off the wall. That is bonkers. That is beyond belief. Sadly, he didn’t have that kind of pull in Chittenden County. Or Franklin County. Or a few other places. He came up just a bit short.”
O’Connor narrowly lost to then-Attorney General Jerry Diamond, 50-48. Diamond was then clobbered that fall by Republican Richard Snelling.
O’Connor never ran for statewide office again.
At 74, O’Connor said he thought the time was right to retire. He said he’s still healthy and wants to spend more time with his three grandsons, Daniel, 8, and Jacob and David, who are 4-year-old twins.
That was illustrated by his wife’s Martha’s absence from last Thursday’s party to attend Daniel’s music recital at Vernon Elementary School in his grandpa’s stead.
He saluted his wife for all the help she provided over the years, both in raising their three children and in running a small-town law office.
“Over the past 50 years, she has worked very closely with me at the office. You look back and see who has been constantly there, and I’ve many secretaries and many associates, but I had one wife who was shoulder-to-shoulder with me — answering the phone, taking messages at night, and constantly being on call.”
When he graduated from Georgetown Law in 1961, Washington was swept up in the excitement of John F. Kennedy’s presidency. It would have been easy to stay in Washington, but O’Connor chose to come back home to Brattleboro. It is a decision he has never regretted.
“I say now, without any question, except for asking my wife to marry me in July of 1961, the best thing I did was to come back here and to begin the practice of law,” he said.
“From hearing stories from my classmates practicing in New York and Washington, I think the interaction is so difficult that they burn out faster than we do here,” he added.
That lack of burnout means that while O’Connor is giving up full-time work, it will be tough to make that happen in practice.
“He’s not retired,” said Crispe. “He’s going to have people chasing him for years to come.”