fb-pixel Skip to main content

Love never grows old

Gerry Doherty's first love left him for the convent. Nearly 70 years later, after spending a career immersed in the law and politics, he married someone who left the convent.

Regina Quinlan and Gerry Doherty at their wedding at St. Mary's Church in Charlestown.
Regina Quinlan and Gerry Doherty at their wedding at St. Mary's Church in Charlestown.Doherty family

Gerry Doherty was a Harvard freshman in 1947 when he attended a dance at the YMCA in his native Charlestown.

He spied a tall, attractive Cathedral High junior named Margaret Crotty. After their first dance, Gerry was, as he recalled in his 2017 memoir, smitten.

Their romance was just blooming when Gerry was diagnosed with tuberculosis. During the two years he spent in treatment in upstate New York, Margaret wrote him regularly and visited him — a risky proposition.

But they were in love, and when he returned to Charlestown in 1950, their courtship resumed. She graduated from Regis College and became a school teacher. The night after he graduated from Harvard in 1952, Gerry took Margaret out for dinner.


They had grown up together in Charlestown and Gerry imagined they would grow old together in Charlestown, as husband and wife. But Margaret said she had something important to tell him: She was leaving him. Not for someone else, but for the convent.

She became a nun with the Sisters of Holy Cross in Indiana. A few years later, she became ill with cancer and died.

“She hadn’t turned 30,” Gerry recalled years later.

You never get over your first love, but Gerry moved on. Two years after Margaret left him, he married Marilyn Dillon, a teacher’s aide.

Gerry got a law degree, got elected as a state representative, and began lifelong friendships with the three Kennedy brothers — Jack, Bobby, and Ted — serving on their various campaigns. He was one of the few non-family members allowed into the Kennedy inner circle.

Gerry was successful in law and politics because he followed the advice the poet Robert Frost gave Jack Kennedy: be more Irish than Harvard. He was a political consultant and strategist years before those words became part of the lexicon, working not for money but out of loyalty to the Kennedys and their ideals.


When Marilyn got sick, Gerry nursed her and remained at her side until she died four years ago, at the age of 85. They had been married 61 years.

After Marilyn died, Gerry began spending a lot of time with Regina Quinlan, a retired judge.

Two years ago, after receiving an invitation to Gerry’s and Regina’s wedding, I visited Gerry at his law office on Franklin Street and jokingly suggested he was robbing the cradle, because while he was 90, Regina was a spry 75.

“I always wanted to marry a nun,” Gerry Doherty replied.

A nun for 10 years, Regina Quinlan left the convent for the law. She made a name for herself as a fierce litigator, defending the First Amendment rights of dirty book stores in the Combat Zone. She later served as a Superior Court judge.

Regina’s and Gerry’s annual Christmas party was a who’s who of legal and political bigshots and ordinary Charlestown folks. Gerry continued to receive visitors at his law office, where many sought his counsel, legal and otherwise. He was a generous man with his time and checkbook.

Gerry Doherty died last week in the house on Washington Street where he was born. He was 92.

Regina told me the coronavirus may have prolonged his life. Besides days at his law office, he had typically been out most nights — something for the Kennedy Library or Malden Catholic or Suffolk Law School or Harvard.


The pandemic forced him to stay home and he settled into a healthy routine. He spent hours on his exercise bicycle and lost his pot belly. He continued to wear a dress shirt and Ferragamo tie every day.

“The last four months were good,” Regina Quinlan Doherty said. “The day before he died, he was on his bike for three hours. He was in a really good mood. He went to sleep and didn’t wake up. In the morning, I got up and his eyes were closed. It was a really nice way to go.”

A nice way to go for a man for whom love and loyalty never grew old.

Kevin Cullen is a Globe columnist. He can be reached at kevin.cullen@globe.com.