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* Isabel posted this story in a roundup earlier this , but I wanted to make sure to highlight it for you: “The real-life spy who stumbled into Glenn Poshard’s campaign for governor,” by Abdon Pallasch…

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.

Abdon told me this crazy and fascinating yarn over dinner at one of our favorite Chicago restaurants not long ago. You gotta click here and read the whole thing.

posted by Rich Miller
Wednesday, Apr 10, 24 @ 8:40 am

Comments

This is not a funny story.

Comment by Three Dimensional Checkers Wednesday, Apr 10, 24 @ 8:57 am
Referring to George Ryan as a conservative Republican is a rather spurious take.

Comment by Ducky LaMoore Wednesday, Apr 10, 24 @ 9:25 am
fascinating story Abdon is a great guy & still a great reporter

Comment by Amalia Wednesday, Apr 10, 24 @ 9:38 am
Irish politics are messy and complicated. I’ll just say there is nothing noble about what Mr. Rupert did.

Comment by It's Just a Pill Wednesday, Apr 10, 24 @ 9:51 am
Very interesting. I remember the campaign and Glenn. As an at will, my job depended on Glenn losing. Glenn really was a man of integrity and folksy country charm. While I was on the opposite side of Glenn (back then it was friendly difference of opinion on policy not a hate filled combat against an evil force), I worked with him in his position as State Senator on many issues. Always noting that southern politeness. Great story and great man.

Comment by Norseman Wednesday, Apr 10, 24 @ 9:55 am
Loved Glenn but his campaign was so underfunded they could barely keep a copier running. Thats when I learned I would never work for a broke candidate ever again.

Comment by low level Wednesday, Apr 10, 24 @ 10:57 am
The US interfering/setting up a massive taxpayer funded elaborate International money laundering web to interfere in international politics what a shock.

Comment by Frida’s boss Wednesday, Apr 10, 24 @ 11:21 am
===they could barely keep a copier running===

And that has what to do with the topic of an FBI mole taking a major role in the campaign and thoroughly bungling it?

Comment by Rich Miller Wednesday, Apr 10, 24 @ 11:28 am
===…to interfere in international politics what a shock.===

International politics? The US government was working to disrupt a terrorist network. The IRA and its many splinter groups used violence, murder, bombings and other terrorist tactics. Just because the IRA had a lot of sympathizers in the US is not a good excuse to turn a blind eye to the fact that they were terrorists.

I applaud the FBI for going after the enablers and moneymen in this country who financed murderers. And I say that as a proud Irish American Catholic who supports a united Ireland. I have no kinship with cowards who chose violence when the politics didn’t go their way. The Good Friday Peace Accords were the best thing to happen to that island since 1922.

Comment by 47th Ward Wednesday, Apr 10, 24 @ 12:09 pm
===The US interfering/setting up a massive taxpayer funded elaborate International money laundering web to interfere in international politics what a shock.===

You get that it was to fight terrorism and its funding sources in the U.S., right?

Comment by Nick Name Wednesday, Apr 10, 24 @ 12:15 pm
==I applaud the FBI for going after the enablers and moneymen in this country who financed murderers. And I say that as a proud Irish American Catholic who supports a united Ireland. I have no kinship with cowards who chose violence when the politics didn’t go their way. The Good Friday Peace Accords were the best thing to happen to that island since 1922.==

Hit it on the head. Especially when there was a peace agreement on the table and all those people giving money wanted to do was sabotage the negotiations and get bombs going off in the streets again.

Comment by ElTacoBandito Wednesday, Apr 10, 24 @ 12:32 pm
The question I would have is did they ever make the case that the cash was used for violence and not literally to support the families of political detainees? Because supporting families sounds kosher under the law, but obviously terrorism is not.

Comment by cermak_rd Wednesday, Apr 10, 24 @ 1:03 pm
Stay on topic, people.

Comment by Rich Miller Wednesday, Apr 10, 24 @ 2:32 pm
The bottom line is that when someone tells you “they know a guy” when you need something done hang up the phone or walk out of the room.

Comment by Demoralized Wednesday, Apr 10, 24 @ 3:42 pm
The conventional wisdom locates the Irish in Chicago on the south side, because of the Daleys and Madigans of the world, so it is a bit ironic that people were fundraising for the IRA on Madison St. and North Ave. Not news to me, however.

Comment by Three Dimensional Checkers Wednesday, Apr 10, 24 @ 4:43 pm
Somebody must have put water in Rupert’s whiskey.

Comment by Dotnonymous x Wednesday, Apr 10, 24 @ 7:18 pm
Oh , man. I can truthfully attest, I was the guy who built Poshard Website 2.0, over that summer, so I didn’t overlap with Dave at all, but I heard stories. 1998 was still the heady days when basically anyone could walk into lots of even statewide and say, “Hey I’ll do your website” and they’d be like, “For free? Ok.” I don’t think Joe Novak even knew of its existence (or at least cared about it) until the final weeks of the campaign.

It was no masterpiece but I think I can attest, it was a better campaign website than Dave’s.

Comment by ZC Wednesday, Apr 10, 24 @ 7:20 pm