Illinois Politics: Always interesting, sometimes stranger than fiction
The real-life spy who stumbled into Glenn Poshard’s campaign for governor
The real-life spy who stumbled into Glenn Poshard’s campaign for governor
Here’s a story about Illinois politics you haven’t heard.
The name you remember is Glenn Poshard, former congressman who nearly became governor of Illinois in 1998. He served as president of Southern Illinois University and is still revered as the undisputed king of downstate Democrats.
Every political campaign worries about spies or moles infiltrating their ranks. But Poshard’s campaign for governor of Illinois really did have a certified spy – though Poshard’s campaign was never the target.
The shadowed name in this story is Dave Rupert, a Chicago trucker recruited by the FBI to infiltrate a militant offshoot of the Irish Republican Army that was trying to blow up the peace process in Northern Ireland.
Poshard was branded a bit of a long-shot when he launched his bid for governor in 1997. He represented the southern tip of Illinois, closer physically and culturally to Memphis than Chicago. Consistent with the views of many of his constituents, Poshard opposed abortion, gay marriage and gun control – which would be a tough sell on Chicago’s lakefront.
But many of Poshard’s more liberal fellow Democratic congressmen backed him because he was in the trenches with them on bread-and-butter economic causes. Unions were such fans of his hooray-for-the-little-guy populism that he snared the coveted endorsement of the state AFL-CIO in the primary.
Poshard had a reputation for personal integrity and plenty of folksy country charm. His fights against corporate interests led him to refuse to take money from Political Action Committees – a noble practice that would confound his fund-raisers.
Dave Rupert was the last guy you’d expect to be able to fool street-smart IRA leaders practiced in sniffing out British spies. A 6’7” protestant from upstate New York with no Irish roots, Dave had to be creative to get the Irish rebels to let their guards down. But by stretching his stories of life as a trucker into actually being a smuggler on the U.S. and Canadian borders, Dave won them over.
Dave was simultaneously infiltrating IRA groups in Ireland and their financial support groups in Chicago. He passed himself off as a wealthy businessman able to travel often to Ireland. It was actually the FBI paying for his flights. The FBI even set him up running a pub on Ireland’s West Coast to make inroads with IRA supporters.
In fine Chicago tradition, Dave told us he made himself the bagman for these U.S. support groups, carrying over envelopes of cash raised in Irish pubs here allegedly to support the families of IRA political prisoners in Northern Ireland – but with which the U.S. and British governments alleged also funded military operations.
When Dave showed up in Ireland with envelopes full of cash, people were happy to see him. And Dave started climbing the ranks of IRA splinter groups there.
The FBI set Dave up with a phony trucking office on Halsted Street in Canaryville. He bought a program to teach himself how to create websites, which were just becoming a thing.
Poshard’s good friend, Congressman Bill Lipinski, recommended a young, politically-involved woman named Catherina to manage Poshard’s campaign office. She had been active with Lipinski’s operation and with Sheriff Michael Sheahan’s 19th Ward organization where she grew up.
She would work for Sheahan in the Cook County Jail. Also working for Sheahan as a night janitor at the Maywood courthouse was Frank O’Neill, a beloved former IRA member, boxer and West Side Pub owner. Frank was probably too old to be working as a janitor but he did such a good job that Sheahan said he got compliments on how clean the Maywood courthouse looked once Frank started working there.
Frank headed up the Friends of Irish Freedom, one of those groups raising money to send back to Ireland that Dave was infiltrating. Catherina was an active member. Dave told them he did websites. They asked him to do the website for the Friends of Irish Freedom. When infighting among group members broke out and Frank, Catherina and others splintered off from that group to form the new “Irish Freedom Committee,” Dave did the new group’s website too.
Catherina had a great idea: Why not have Dave do the website for the Poshard Campaign?
She approached Poshard senior staffer David Stricklin, who was getting the office going before Joe Novak took over as campaign manager, and said, “I got a guy.” Stricklin says he said, “OK.”
In a move he later realized could put the FBI in an awkward position, Dave agreed to do it. He grabbed some campaign literature from the campaign office on Randolph Street and headed off… to Ireland.
“I was the Webmaster for Poshard, but got into a real sticky wicket, so to speak,” Dave told us, “Because, um, that … could be construed as being involved in a gubernatorial election.”
The main target of Dave’s spying in Ireland at this point was Joe O’Neill (no relation to Frank), an elected Republican Sinn Fein town councilor in Bundoran. Joe O’Neill was also a senior operative in the Continuity IRA. Dave had become a trusted confidant of Joe, who let him use his real estate office computer to compose Poshard’s website.
Poshard said he never knew his website was created at an IRA operative’s office in Ireland.
When he put up the website, Dave and Catherina were pretty impressed with it. It was fairly simple, just two pages. Some campaign staff were less impressed. Dave used an American flag as the backdrop for a Poshard speech which made it hard to read.
The website was not as elaborate as John Schmidt’s. Schmidt, who had been Mayor Daley’s chief of staff and the number-3 man at the U.S. Justice Dept., was the pundits’ favorite to win the Democratic primary.
U.S. Attorney Jim Burns was also in the race, hoping to follow Jim Thompson’s path to the governor’s mansion with early support from House Speaker Mike Madigan. And Attorney General Roland Burris had won four statewide elections and had reason for optimism.
All four candidates had plausible paths to the Democratic nomination.
Poshard’s principled stand against taking corporate PAC money meant his donations came in small chunks. And Poshard asked that all those small-money donors be listed on his website.
So Dave, the unpaid volunteer, said he spent countless hours at his office on Halsted and at Joe O’Neill’s office in Ireland entering all those donor’s names.
It was too much for the campaign computers to hold. Dave told campaign staff the only way he knew to fix the problem was to reformat the whole system, which could erase all those donor records.
Dave says the campaign told him to go ahead and try it. He did.
The website crashed. Loads of donor files were lost.
The campaign says it was completely Dave’s screw-up.
Rumors began to circulate that Dave was a mole from John Schmidt’s campaign.
The rumors were half-true. Dave was mole alright. But not from the Schmidt campaign.
Dave and Catherina left the campaign. The rest of the staff picked up the pieces and re-did the website.
The snafu was a nuisance, but not fatal. Poshard’s staff contained it well enough that John Schmidt and Roland Burris say now they never heard about the collapse of Poshard’s website.
With that big labor endorsement from the state AFL-CIO, Poshard won the primary with 38% of the vote to 31% for Burris and 25% for Schmidt.
Poshard entered the general election with promise of turning out the downstate vote and taking the governor’s seat back for the Democrats for the first time in more than 20 years.
But Chicago’s lakefront liberals were so turned off by Poshard’s social conservatism that some of them voted for the conservative Republican who some women legislators blame for killing the Equal Rights Amendment in Illinois. Or those voters stayed home.
Poshard’s principled stand against “big money” meant Republican George Ryan could outspend him $13 million to $3 million.
Poshard brought out more Democratic votes than usual in Southern Illinois, but it wasn’t enough.
George Ryan beat Poshard with 51% of the votes and later went to prison for corruption.
Poshard went back to Southern Illinois and became president of Southern Illinois University. He’s still the honored guest and lead speaker at just about every gathering of Southern Illinois Democrats.
Dave became a trusted confidant of Mickey McKevitt. who was charged with directing terrorism. With Dave as lead witness, McKevitt was sentenced to 20 years in prison, disabling the Real IRA.
We interviewed Frank O’Neill, Catherina, and other members of the Friends of Irish Freedom/Irish Freedom Committee extensively at the time and attended some of their meetings at Murphy’s Pub in Forest Park where they passed the jar for the cause.
I also interviewed members of Poshard’s campaign staff 20 years ago and again recently.
Frank O’Neill passed away at age 88 in 2011. Jim Burns passed away in 2020 after serving as inspector general for Illinois Secretary of State Jesse White.
Even after Dave’s role as a spy for the FBI was revealed in 2001, Poshard, Burris and Schmidt said in recent interviews that they never realized an international spy designed Poshard's first campaign website – and crashed it.
Dave lives off the grid somewhere in the United States.
Editor’s note: My former colleague at the Chicago Sun-Times, Bob Herguth, and I, have just begun releasing our 12-episode podcast: Underbelly: The Rebel Kind, recounting Dave’s wild spy adventure. https://podcasts.apple.com/us/podcast/there-once-was-a-trucker-from-chicago/id1680549673?i=1000649038201
We taped interviews with Dave 20 years ago in which he walked us through his unbelievable journey, including his interactions with Illinois political operatives and activists.
Abdon Pallasch was a resident staff writer for the Chicago Tribune during the 1998 Illinois governor's race then became political reporter for the Chicago Sun-Times. He now serves as director of communications for Illinois State Comptroller Susana A. Mendoza.
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