By Abdon Pallasch, Special to Florida Bulldog
Just months after it started 26 years ago, Northern Ireland’s peace process could have collapsed after an IRA splinter group killed 31 people, mostly women and children, with a bomb in the small town of Omagh.
But that splinter group largely dissolved thanks in large part to an American trucker-turned spy Dave Rupert, who worked his way up to the top of the “Real IRA” and helped convict its leader.
And all that started with a chance romantic encounter between Rupert and Tallahassee lobbyist Linda Vaughn in an Irish pub on St. Pete Beach.
President Joe Biden appeared in Belfast last year to celebrate 25 years of peace. Biden never mentioned Dave Rupert’s name. But those involved in holding the peace process together credit Rupert with taking out the main threat to peace.
“Dave Rupert was extremely brave and courageous and thank God he escaped alive,” said Michael Gallagher, whose son Aidan was one of the 31 killed by the Real IRA’s car bomb in Omagh. “If they had had even a clue that he was passing on information to anybody, he would have been dissected. His body would never have been found.”
Rupert was the main witness at the 2003 trial of “Real IRA” leader Mickey McKevitt in Dublin on charges of “Directing Terrorism.” For years, Rupert had portrayed himself as a smuggler moving marijuana and other contraband across the Mexican and Canadian borders.
THE TRUCKER MEETS THE IRA
A 6’7” Protestant from upstate New York, Dave Rupert was about the last person you’d ever expect to fool Mickey McKevitt, the cunning leader of the Real IRA.
Rupert had no training as a spy, but he was a good talker, and was able to portray himself to McKevitt as a fellow smuggler, moving marijuana and other contraband across the Mexican and Canadian borders.
McKevitt used to smuggle himself out of Ireland in the bed of a truck to get to Europe and Africa to buy weapons from former Libyan dictator Muammar Gaddafi.
The truth of the matter is the only border smuggling Rupert did was stuff fire-crackers in his shorts crossing from Canada into the U.S. as a kid.
But Rupert knew enough about the trucking business to fool McKevitt and his cohorts who grew up smuggling weapons, goods and fighters across the Northern Ireland border.
Rupert implied to McKevitt that he had a role in his brother Dale’s ’96 arrest in Fort Lauderdale for smuggling more than a ton of marijuana that landed him 18 months in the Okeechobee Correctional Institution.
As Rupert testified against McKevitt at his 2003 trial in Dublin for “Directing Terrorism,” McKevitt’s lawyers thought they’d nail Rupert with the story of his and his brother’s alleged weed-running in Florida.
Check the records, Rupert said. Contrary to what he’d earlier told McKevitt, Rupert was never implicated in his brother’s case.
“I was sorry he got caught,” Rupert said. “He was 55 years old and should have known better.”
A PODCAST WITH DETAILS
New details of Rupert’s spy adventure are emerging in a podcast L.A.-based Entropy Media has begun releasing called Underbelly: The Rebel Kind, based on never-before-heard tapes my colleague Bob Herguth and I made 20 years ago of Rupert discussing his adventure. The tapes became the subject of a federal court case.
Back in the early ’90s, Rupert was running his trucking company on the Florida Gulf Coast. Living on John’s Pass, near St. Petersburg, he watched gambling boats head out to international waters and fantasized about running hovercraft out to permanently anchored gambling yachts as a way to make big money.
It was a strange time in Rupert’s life. He had just dumped his second wife, who he admitted was a wonderful woman, just because he wanted to chase other women.
So he headed down to his usual hangout, Willy’s on the Gulf side. But as he approached Willy’s, he heard catchy music from across the street at the Harp & Thistle Pub.
Guinness the Duo, husband-and-wife singers Jim & Laura Farrell from Prince Edward Island, Canada, played ballads that reminded Rupert of the bluegrass music of his youth on the New York side of the Canadian border.
Laura Farrell’s siren song led him into the storied Harp & Thistle Pub where he became a regular and where, one night, a beautiful redhead caught Rupert’s eye. Rupert learned Linda Vaughn had brains and drive to match her looks.
‘THE RED-HAIRED TERROR’
A high-powered liberal lobbyist in Tallahassee, Linda Vaughn is a reason you can’t smoke indoors in Florida.
“She was so assertive and aggressive; she actually took on some of the deemed ‘black hat lobbyists’ up there that were lobbying for tobacco products. She really would go toe to toe with them. She was a real go-getter,” former State Rep. Lars Hafner recounted at the former Harp & Thistle, now Oyster Shucker.
“Do you remember Linda Vaughn?” I asked Peter Rudy Wallace, former Speaker of the Florida House of Representatives, in his law office last year.
“The Red-Haired Terror? Are you kidding?” he replied. Vaughn started as an aide to former State Sen. Jeanne Malchon and became a ferocious advocate in the capitol, fighting an often-losing battle against guns as the Florida lobbyist for the Brady Center to Prevent Gun Violence.
“I was in the Harp & Thistle drinking and this lady came in one night and this was Linda Vaughn and she was from Tallahassee and she was a political consultant,” Rupert said. “She had been Florida campaign manager for Paul Tsongas when he ran for president. She had also been a lobbyist for Noraid.”
Noraid or “Irish Northern Aid” was an American group that raised funds it said went to support the families of IRA political prisoners. The U.S. and British governments alleged the money funded the IRA.
I was a regular at the Harp & Thistle when I worked as a reporter for The Tampa Tribune in the ‘90s and may well have been there the night Rupert met Vaughn. They bonded over their mutual love of Ireland. Rupert had no Irish roots, but had gone to Ireland with an earlier girlfriend and the old-fashioned way of life he found on Ireland’s West Coast reminded him of his childhood in rural upstate New York.
REBEL SONGS
Rupert’s education in Irish history was already beginning as he listened to Laura Farrell’s heartfelt rendition of Tommy Sands’s “All the Little Children:”
“And we’re singing of the times when the sun will always shine
And armored cars and tanks will fade away.
People will be one, and the fighting will be done
And all the little children they can play.”
Rebel songs sung in Irish pubs around the globe have helped fuel the fight to reunite the Emerald Isle, and they would be a major part of Rupert’s life during his seven-year ordeal.
“In a way, I think Irish folk music is responsible for the peace in The North,” Jim Farrell said. “The rebel songs offended some people, but it also made some other people say. ‘What’s really going on here? How come they’re singing these songs?”
Rupert told Vaughn he agreed with her liberal politics. He suggested they step out on the veranda for some fresh air.
“Linda was a party animal,” said her friend and fellow liberal Tallahassee lobbyist Barbara DeVane. “Linda loved Guinness. She loved Irish music. She played the spoons. That’s why she loved the Harp & Thistle so much.”
“Linda was a dynamo,” said Vaughn’s friend Elaine Grace, a retired nurse who volunteers at the Dali Museum in St. Petersburg. “She entered a room and she was smiling and she was chatting. You’d get a hug from Linda, that’s for sure. She really cared deeply about people. Once that Irish music was playing and she was playing her spoons and smiling and laughing and making people around her happy as well.”
Here’s Rupert’s take on how the night wound up: “By the end of the evening, Linda and I had both been drinking a lot, so, as a friend, I offered to let her stay at my place in Treasure Island since she was staying in Sarasota. Quite a drive when one has been drinking. Ah, chivalry at its finest. Also a good pick-up line. The rest is history.”
INTRODUCTION TO THE FIGHT
“He wasn’t really the same type of guy that I usually saw Linda dating,” DeVane said. “He was, big guy, but, you know, I didn’t exactly know what their whole relationship was. I guess he fulfilled some need in her because they dated for a while. But I was sure that she probably would introduce him to Ireland.”
And she did. Between dating in the Tampa area and Tallahassee, Rupert and Vaughn visited Ireland, where she showed Rupert a side of the Island he hadn’t seen, introducing him to fighters in the armed struggle against the British.
“She was very much an Irish, um, fanatic, some might say, because she went all out,” DeVane said. “That’s why she loved the Harp & Thistle so much. And she made speeches in Ireland during ‘The Troubles.’ She organized Sligo, Ireland, as being Tallahassee’s sister city.”
“She was passionate about Ireland,” Elaine Grace said. “I just remember her talking about that they were really oppressed and that they wanted the Brits out of Ireland.”
Grace’s husband, Bill, remembers challenging Vaughn when she defended leaders of the IRA and the political party sometimes called its political wing, Sinn Fein.
Vaughn’s eventual husband, Irish-American musician Kevin Mangan, says she was deeply immersed in the Irish cause when they met. She was the only American invited onto the stage with the mothers of the Irish prisoners on hunger strike at a 1984 rally in Bundoran, County Donegal, Mangan said.
“I know there were times when she went in to visit the prisoners there,” Mangan said. “They’ve got very little communication from home. So what she would do is get messages from the family. They would wad it up into a small square of tinfoil and she would put it in her mouth. And then when she met the prisoners, she would kiss them and pass that message over from home.”
THE MACBRIDE PRINCIPLES
Linda was the driving force behind passing the MacBride Principles in Florida, a law that prohibits the state from investing in companies found to be engaging in discrimination against Catholics in Northern Ireland.
“I think one of her proudest moments was when Derek Warfield from the Wolfe Tones presented her with the Sean MacBride Humanitarian Award,” Mangan said, referring to the Irish music group named for Irish hero Theobald Wolfe Tone. “She single-handedly got the Florida Legislature to divest their interest in companies that were practicing unfair hiring in the North where they wouldn’t hire Catholics.”
But back in the early ‘90s it was Dave Rupert walking into the rebel pubs with Linda Vaughn on his arm, which won him instant credibility with IRA-supporting pub owners like Joe O’Neill and Vincie Murray.
Joe O’Neill was a town councilor in Bundoran, elected as a member of Republican Sinn Fein, aligned with the “Continuity IRA,” which had broken off from the “Provisional IRA.” O’Neill ran a pub in Bundoran where he sang ballads, and he was a top real estate agent in the town and a top recruiter of young men into militant groups.
Vincie Murray owned a pub in Sligo, which Vaughn had established as a sister city of Tallahassee. Murray was a town council member in the Sinn Fein party.
Both O’Neill and Murray schooled Rupert on the history of British Oppression of the Irish. There was at least 800 years to catch Rupert up on. Rupert was dating Linda, so they figured they could trust him.
BECOMING A ‘LOCAL HERO’
“We were in Vincie Murray’s bar one night. We’re sitting there drinking, and of course at the time Vincie Murray’s pub was an IRA pub, you know, and we had rooms upstairs,” Rupert recalled. “So we’re sitting there one night and I was giving this IRA thing some thought. And I said, ‘Well, you know, the problem is you’re not sending up home enough body bags to England. You know?’ I says, ‘That’s how that the Vietnamese won the war – the body count, you know?’
“It wasn’t a statement of support, so to speak, [but rather an] observation. But immediately I was, a local hero.”
In the world of Irish Republicanism – meaning those who favor reuniting British-controlled Northern Ireland with the Republic of Ireland – the goal is to get the British out of Ireland, all of Ireland, at virtually any cost. So saying they need to send more body bags back to Britain was something that got Rupert a lot of credit in those circles.
Rupert didn’t think too much of his off-the-cuff comment at the time. As he and Vincie Murray walked outside Murray’s pub in Sligo, a police car cruised by. Murray pointed to the car and told Rupert, “Well, they’ve got your picture now too.”
A year or two later, after Rupert had broken up with Linda, married and divorced his third wife, and begun dating the manager of his Chicago truck stop who would become his fourth and current wife, his secretary told him he had a visitor he probably wouldn’t want to see.
“So, in comes Ed Buckley, and I don’t know if you know Buckley at all, but I kind of reference him as like, Yosemite Sam, you know, it’s like a flurry of activity around him and his hands are going,” Rupert said.
Ed Buckley introduced himself as an FBI agent.
AN FBI OFFER
The possibilities started racing through Rupert’s mind. Was it the $750,000 in income taxes he owed the IRS on a previous business failure? Was it the stories of Rupert smuggling goods over the Canadian or Mexican borders in his trucks?
The truth actually came as a relief to Rupert.
“He threw these pictures down on the desk,” Rupert recalls. “The one picture was of me and Vincie Murray. And then they had another picture of me and Joe O’Neill and getting in the car in Bundoran and it was just like: ‘Why are you – an American – over with these two?’”
Is that all? Rupert exhaled. They were just drinking buddies. Rupert had not been recruited into any illegal activities.
Buckley, who had been a thorn in the side of Irish-American activists in Chicago for years, had a proposition for Rupert: How would he like to go to work for the FBI spying on his drinking buddies? Just keep his eyes and ears open and the FBI would pay for his trips to Ireland.
Rupert took Buckley’s card and said he’d think about it. On his next visit to Ireland, afraid that Joe O’Neill and his “Continuity IRA” comrades would find Buckley’s card in his pocket and kill him, Rupert tore the card into small pieces and ate it.
And with Linda Vaughn long out of his life, so began Rupert’s career as a spy.
FBI AND MI5 PAY RUPERT MILLIONS TO SPY
Over the subsequent seven years, Rupert would convince the FBI to advance him money to lease a pub for him to run on the Northern Ireland border to ingratiate himself with IRA supporters. Rupert was so effective that over 20 years the FBI and Britain’s MI5 would pay him more than $10 million for his efforts infiltrating dissident groups and providing crucial testimony against the militants.
As much of the IRA followed Gerry Adams and Martin McGuinness into the peace process that overwhelming majorities of voters on both sides of the border approved, IRA Quartermaster Mickey McKevitt led perhaps the most lethal of several breakaway factions of the IRA, the “Real IRA,” that wanted to keep setting bombs to drive the British out of Northern Ireland.
MI5 heard the FBI had a secret weapon – Rupert – in a position to gather valuable information on the dissident groups. They never dreamed he would work his way up to be one of McKevitt’s most trusted right-hand men.
“[MI5] couldn’t believe that McKevitt was coming to see me,” Rupert said. “I knew he was a bad guy. They’ve been chasing him for 25 years, and really never got anybody close to him, and, here I walk in and, you know, ‘Hi, how ya doin’?’”
The second episode of Underbelly: The Rebel Kind features Rupert’s time in Florida, when Linda Vaughn introduced him to Irish Republicanism.
VAUGHN’S LEGACY
Linda Vaughn died in 2015 of pancreatic cancer. Her husband felt it was important to talk to us because, he said: “I think one of the saddest things, and one of the reasons why I really wanted to do this, was that her last trip over there was 2014. There was a rally, and Joe O’Neill was there. And she walked up to him and said, ‘I don’t know if you remember me, I’m Linda Vaughn.’”
“And he said, ‘Oh, indeed I do. You’re the one who brought that traitor into our midst,’” Mangan said.
That was the unkindest cut for Linda Vaughn. She went to her grave feeling angry and betrayed by Rupert.
Vaughn’s husband says she’s been unfairly judged, “For all of the good that she did, and how hard she fought over there, on the ground, that, ultimately shouldn’t be her legacy.”
Still, with Rupert’s testimony McKevitt was sentenced to 20 years in prison for directing terrorism, effectively shutting down the Real IRA and allowing the Irish peace process to advance.
McKevitt was never charged directly for his role in the Omagh bombing, but he and his cohorts were found civilly liable. He died in 2021 without paying any money to the victims.
“We were awarded £1.6 million,” Gallagher said. “But we never received and probably will never receive a single penny because those people dispose of their assets,”
Rupert, 72, lives off the grid somewhere in the United States.
(Abdon Pallasch was a staff writer for The Tampa Tribune, The Chicago Tribune and The Chicago Sun-Times. He has published stories in The Irish Times and The Belfast Telegraph. He now serves as directore of communications for Illinois State Comptroller Susana Mendoza.)
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