The paintings were torn off the walls one by one at gunpoint. Only the most valuable items were taken. A Vermeer. A Goya. A Velázquez and others.

When the Irish Republican Army band of robbers drove off at night from a property south of Dublin in April 1974, 19 masterpieces were crammed into the car. Amid the loot sat the architect of the theft: Rose Dugdale, an Oxford-educated heiress who once curtsied to Queen Elizabeth II during a debutante soiree at Buckingham Palace.

Ms. Dugdale, who had left her previous life behind, viewed looted art as a bargaining chip for the release of IRA prisoners. Instead, the paintings were recovered and she was imprisoned – capping her development as she turned to the IRA’s fight against British rule over Northern Ireland, including once leading an audacious attempt to bomb a police station from one hijacked helicopter.

Ms Dugdale, who died in a Dublin care facility on March 18 aged 82, also enjoyed scorning the upscale English background she rejected. Time magazine called her the “Renegade Debutante” – she committed the art heist just weeks after newspaper heiress Patty Hearst was seen robbing a San Francisco bank with a self-proclaimed revolutionary group called the Symbionese Liberation Army.

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

The decades-long sectarian bloodshed in Northern Ireland known as the Troubles had many backstories before peace deals were reached in 1998 that largely ended the fighting that claimed more than 3,500 lives. The IRA once found support in the Irish diaspora and even in regimes such as Libya, Britain claimed. One day in late 1973, the unlikely militant, Ms. Dugdale, entered the picture.

She contacted IRA commanders and offered to help them buy some weapons in return for joining their circle, court documents and biographies say. Ms Dugdale was no stranger to the IRA. She had already made headlines for rebelling against her family tree.

Ms Dugdale grew up with all the advantages of her wealthy ancestry – a father who ran a lucrative insurance syndicate at Lloyd’s and a mother who came from a wealthy old-money family. As a teenager, Ms. Dugdale took a classic Grand Tour of Europe and then attended the Queen’s debutante ceremony in 1958, where the young women entering high society nibbled on chocolate cake and fooled around with royalty.

Ms. Dugdale did not want to attend, she recalled, but was persuaded by appeals from her mother. Later, at St. Anne’s College, part of Oxford University, Ms. Dugdale showed further sparks of discontent. She disguised herself as a man and stormed into the Oxford Union debating club to protest its all-male membership.

Ms. Dugdale then earned a doctorate in economics and began a career in academia. However, their views were shaped by other forces, such as the anti-war protests and civil rights movements of the 1960s.

After a trip to Cuba, she became interested in communism. At the beginning of the 1970s, she resigned from her teaching position, sold her house in London’s posh Chelsea district and cashed in her share of the family’s ownership of Lloyd’s. She used her small fortune for projects such as distributing food and relief supplies to low-income families. She took part in marches against apartheid and traveled to conflict-torn Northern Ireland with her then-partner Walter Heaton, a former British army soldier who described himself as a “radical socialist”.

In June 1973, Ms Dugdale and Heaton were arrested following a burglary on the Dugdale family’s 600-acre estate in Devon, the same grounds where she had ridden her pony Eros as a girl. Ms Dugdale and Heaton were charged with stealing paintings, silverware and antiques worth more than $150,000. Police claimed Heaton, who had links to the IRA, had planned to pass some of the money to the group.

Heaton was convicted and sentenced to six years in prison. Ms Dugdale received a two-year suspended sentence, with the judge saying it was unlikely she would commit any criminal acts in the future. She openly mocked the verdict. “By convicting me, you have transformed me from an intellectual rebel into a freedom fighter,” she told the court. “I don’t know of a better title.”

Within a few months she established a foothold in the IRA. “No, I can’t say I regret it,” Ms Dugdale was quoted as saying in Sean O’Driscoll’s biography “Heiress, Rebel, Vigilante, Bomber: The Extraordinary Life of Rose Dugdale” (2022). “At a certain point, there was no way I could turn back.”

In January 1974, she posed as a freelance photojournalist in County Donegal, Ireland, to rent a helicopter. Once the helicopter was in the air, Ms Dugdale and IRA foot soldier Eddie Gallagher called for the pilot to land. They loaded large milk jugs, called churns, full of explosives on board. The pilot then had to fly over the Northern Irish border to Strabane, where Ms Dugdale and Gallagher threw the improvised bombs at a police station.

The explosive charge failed to explode and the explosives landed without causing injuries. Ms Dugdale called it “the happiest day of my life” because she tried to cause chaos. “It was the first time I felt like I was in the middle of the action,” she told O’Driscoll, “that I was actually doing what I said I would do.”

Less than four months later, Ms Dugdale found herself on the doorstep of Russborough House, the country estate of Alfred Beit, a former British MP and heir to a South African mining fortune. Ms Dugdale pretended to be a French tourist whose car had broken down.

Suddenly her IRA comrades burst in. Beit became angry. Ms. Dugdale guarded Beit and his wife and shouted at the couple: “Capitalist pigs!” she recalled. The IRA gunmen woke a 17-year-old maid from the bathroom to lead her to the rooms containing the valuable works of art. Among the stolen works was that of Francisco Goya “Portrait of Doña Antonia Zárate”; Diego Velazquez “Kitchen Maid at the Supper in Emmaus”; and Johannes Vermeer “Lady is writing a letter with her maid.”

“They deserved it in every way,” Ms. Dugdale said later.

She and the gunmen drove to County Cork, where she booked a cottage under the name Mrs Merrimée. A note sent to the National Gallery of Ireland called for the release of four IRA prisoners from British custody.

Police visited the house during the nationwide manhunt for the paintings. Ms. Dugdale remained in the guise of a lone French tourist, she said. The police were not fooled. During a raid, three of the stolen paintings were found in the cottage. The others were found stacked in the trunk of a car.

By this time, Ms. Dugdale had fled and was eventually caught in the Cork village of Baltimore, a woman’s name Movie about Ms Dugdale’s life, scheduled for publication this week. (The Beit collection was too strike again and again discovered by other art thieves in the following decades.)

Ms Dugdale pleaded “proudly and incorruptibly guilty” and was sentenced to nine years in prison for her role in the robbery and attack on Strabane police station.

After her detention, Ms Dugdale discovered she was pregnant and said the father was Gallagher, a refugee. A year later, Gallagher kidnapped the Dutch industrialist Tiede Herrema in Limerick to demand Ms Dugdale’s release. A siege of his hideout lasting more than two weeks ended with Gallagher’s surrender. Herrema was uninjured.

“You have to remember that these were very exciting times… the world looked like it could change and probably would change,” Ms Dugdale said told Irish state broadcaster RTÉ in 2014: “And whoever you are, you could play a role in this.”

Bridget Dugdale was born on March 25, 1941 on the family estate of Devon in southwest England. At the time, her father was an officer with Field Marshal Bernard Law Montgomery in North Africa. When her father returned home, he nicknamed his daughter Rose.

She graduated from St. Anne’s College in 1962 and then received a master’s degree in philosophy from Mount Holyoke College in South Hadley, Massachusetts. Her application included a letter of recommendation from the writer Iris Murdoch, one of Ms. Dugdale’s professors at Oxford.

Ms Dugdale returned to London in 1965 to work as a government economic adviser specializing in developing countries. After completing her doctorate in economics at Bedford College, London (now part of Royal Holloway College), she remained on campus as a lecturer.

In 1978, she and Gallagher were allowed to marry in prison. She was released in 1980 and reunited with her son Ruairí. Later she started a relationship with Jim Monaghanan IRA bomb maker.

In O’Driscoll’s biography, Ms Dugdale claimed she played a role in the development of IRA bombs used in major attacks in the early 1990s, but no charges were brought.

Ms Dugdale and Gallagher were estranged but they remained married. Her son is among the survivors. Irish media reported the death but no cause was given.

Ms Dugdale spent the rest of her life in Dublin after leaving prison. She worked for various charities and was an active member of Sinn Féin, the political wing of the IRA.

Her death also leaves a mystery: who stole a Vermeer painting? “The guitarist” from a museum in Hampstead, England, in February 1974? A ransom note called for the release of two sisters imprisoned for links to the IRA. No one has been charged in the theft, but authorities said Ms. Dugdale was a prime suspect.

The painting was found in a London cemetery two days after her arrest for the Beit raid. A statement from Scotland Yard said the Vermeer was “leaned against a gravestone, wrapped in newspaper and tied with a string.”

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