Individually, the paintings were forcibly removed from the walls under the threat of guns. Only the most prized pieces were targeted: a Vermeer, a Goya, a Velázquez, and more. In April 1974, a group of Irish Republican Army raiders hastily departed from an estate located south of Dublin, with 19 invaluable masterpieces crammed into their vehicle.

Among the stolen art sat the orchestrator of the heist: Rose Dugdale, an heiress with an Oxford education, who had once graced Buckingham Palace during a debutante soirée, even curtsying before Queen Elizabeth II.

Having abandoned her former life, Ms. Dugdale viewed the stolen art as leverage to secure the release of IRA prisoners.

However, instead of achieving her goal, the paintings were eventually recovered, leading to her imprisonment. This marked the culmination of her transformation as she fully embraced the IRA’s struggle against British rule in Northern Ireland.

Her commitment was evident in her audacious leadership, including orchestrating a daring attempt to bomb a police station from a hijacked helicopter.

Ms. Dugdale, who passed away on March 18 at a nursing facility in Dublin at the age of 82, took pleasure in defying the upper-crust English background she had turned away from. Time magazine bestowed upon her the moniker of the “Renegade Debutante.”

Notably, she executed the art robbery mere weeks after newspaper heiress Patty Hearst was spotted robbing a bank in San Francisco alongside the self-styled revolutionary group known as the Symbionese Liberation Army.

“I love you,” Ms. Dugdale said to her father during one of her court hearings in the 1970s, “but I hate everything you stand for.”

Before peace accords were reached in 1998 to quell the sectarian bloodshed over Northern Ireland, known as the Troubles, numerous backstories unfolded.

The conflict, which claimed over 3,500 lives, saw the IRA garnering support not only from the Irish diaspora but also from regimes like Libya, as claimed by Britain. In late 1973, an unlikely militant, Ms. Dugdale, emerged onto the scene.

She initiated contact with IRA commanders, proposing assistance in procuring weapons in exchange for integration into their ranks, as indicated by court records and biographies.

Ms. Dugdale was not a stranger to the IRA, having previously made headlines for her rebellion against her privileged background.

Raised amidst the luxuries of her affluent lineage, Ms. Dugdale enjoyed the benefits of her father’s successful insurance underwriting syndicate at Lloyd’s, coupled with a mother hailing from a wealthy old-money family.

During her teenage years, she embarked on the customary European Grand Tour and participated in the 1958 debutante ceremony hosted by the queen, where she reluctantly mingled with royalty after being persuaded by her mother.

While at St. Anne’s College, Oxford, she demonstrated her rebellious streak by dressing as a man and infiltrating the male-only Oxford Union debating society in protest.

Despite pursuing a doctorate in economics and starting an academic career, Ms. Dugdale’s ideological leanings were shaped by the antiwar protests and civil rights movements of the 1960s.

A trip to Cuba fueled her interest in communism, leading her to resign from her teaching position, sell her home in London’s upscale Chelsea neighborhood, and divest her share of the family assets in Lloyd’s.

Utilizing the proceeds, she engaged in philanthropic endeavors such as providing aid to low-income families and participating in anti-apartheid marches.

Accompanied by her then-partner, Walter Heaton, a former British army soldier who identified as a “radical socialist,” she ventured to conflict-ridden Northern Ireland.

In June 1973, Ms. Dugdale and Heaton faced arrest following a break-in at the sprawling 600-acre Dugdale family estate in Devon, where she had once enjoyed horseback rides on her pony, Eros, during her childhood.

The duo was accused of pilfering paintings, silverware, and antiques with an estimated value exceeding $150,000.

Law enforcement alleged that Heaton, with ties to the IRA, intended to channel a portion of the proceeds to the organization.

Heaton was convicted and sentenced to six years behind bars, while Ms. Dugdale received a two-year suspended sentence, with the judge expressing doubt about her likelihood of committing future criminal acts.

Ms. Dugdale openly ridiculed the verdict, stating to the court,

“In finding me guilty, you have transformed me from an intellectual recalcitrant into a freedom fighter. I know no finer title.”

Undeterred, she swiftly forged connections with the IRA. “No, I cannot say I do regret it,” Ms. Dugdale remarked, as quoted in Sean O’Driscoll’s biography, “Heiress, Rebel, Vigilante, Bomber: The Extraordinary Life of Rose Dugdale” (2022).

“There was no way, after a certain point, that I would turn back.”

In January 1974, in County Donegal, Ireland, she assumed the guise of a freelance photojournalist to charter a helicopter. Once airborne, Ms. Dugdale and IRA foot soldier Eddie Gallagher coerced the pilot to land, loading large milk jugs, filled with explosives, onto the aircraft.

The pilot was then compelled to fly across the Northern Ireland border to Strabane, where Ms. Dugdale and Gallagher dropped the improvised bombs on a police station.

The charges failed to detonate, and the devices landed without causing harm. Ms. Dugdale described it as “the happiest day of my life” for attempting to sow chaos.

“It was the first time I felt at the center of things,” she confided to O’Driscoll, “that I was truly following through on my convictions.”

Less than four months later, Ms. Dugdale arrived at the doorstep of Russborough House, the country estate of Alfred Beit, a former British Member of Parliament and heir to a South African mining fortune.

Disguised as a French tourist whose car had broken down, Ms. Dugdale’s ruse quickly unraveled when her IRA comrades stormed in. Beit was subjected to rough treatment while Ms. Dugdale stood guard over him and his wife, berating them as “Capitalist pigs!” as she recalled.

The armed IRA members disturbed a 17-year-old maid from her bath to guide them to rooms housing valuable artworks.

Among the stolen pieces were Francisco Goya’s “Portrait of Doña Antonia Zárate,” Diego Velázquez’s “Kitchen Maid with the Supper at Emmaus,” and Johannes Vermeer’s “Lady Writing a Letter with her Maid.”

Nicknamed Rose

Bridget Dugdale entered the world on March 25, 1941, at the family’s Devon estate in southwestern England. Her father, then serving as an officer with Field Marshal Bernard Law Montgomery in North Africa, affectionately dubbed her Rose upon his return.

She completed her education at St. Anne’s College in 1962 and pursued a master’s degree in philosophy at Mount Holyoke College in South Hadley, Mass., with a letter of recommendation from novelist Iris Murdoch, one of her professors at Oxford.

Returning to London in 1965, she served as a government economic adviser specializing in developing countries.

After obtaining her economics doctorate at Bedford College in London, she continued as a lecturer.In 1978, she and Eddie Gallagher were allowed to marry while in prison.

Released in 1980, she was reunited with her son, Ruairí, and later began a relationship with Jim Monaghan, an IRA bomb maker.

In O’Driscoll’s biography, she claimed involvement in developing IRA bombs for major attacks in the early 1990s, although no charges were filed.

Though estranged, Ms. Dugdale and Gallagher remained legally married. She spent her remaining years in Dublin, engaging in charity work and active Sinn Féin membership.Her passing leaves one unresolved mystery: the theft of Vermeer’s “The Guitar Player” from a museum in Hampstead, England, in February 1974.

A ransom note demanded the release of two IRA-linked sisters. Though no charges were brought, authorities considered Ms. Dugdale a prime suspect.

The painting was discovered in a London cemetery two days after her arrest for the Beit heist, propped against a gravestone, wrapped in newspaper, and tied with a string, according to a Scotland Yard statement.