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May 13, 2025 - Weird Little Guys
12:10
Minisode: Pappas v Giuliani

A bite-sized look at the NYPD officer who sued the city for firing him over anonymously mailing racist pamphlets to charitable organizationsSources:​​https://www.nytimes.com/1998/06/17/nyregion/officer-admits-to-racist-mail-and-is-offered-deal-to-retire.html https://www.huffpost.com/entry/sotomayors-defense-of-whi_n_210795 https://www.criminallawlibraryblog.com/wp-content/uploads/sites/335/2016/09/Sotomayor_2002Opinion_Pappas.pdf https://www.courtlistener.com/opinion/2358084/pappas-v-giuliani/See omnystudio.com/listener for privacy information.

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You're listening to an iHeart Podcast.
Explore the winding halls of historical true crime with Holly Fry and Maria Tremarky, hosts of Criminalia, as they uncover curious cases from the past.
The legend of the highwayman suggests men dominated the field, but tell that to Lady Catherine Ferrars, known as the Wicked Lady, who terrorized England in the mid-1600s.
Her legend persists nearly 400 years after her death.
Highwaymen are in the hot seat this season.
Find more crime and cocktails on Criminalia.
Listen to Criminalia on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Call Zone Media Hello listeners, Molly Conger here.
This is something a little different.
It's not a new full-length episode, but it's not a rerun either.
It's just a tiny little bite-sized story about a weird little guy.
I'd like to try to do more of these, just a few minutes about various side characters I found in my research who didn't really warrant their own tangent in an episode.
I recently found myself, for normal, work-related reasons, Combing through the campaign finance reports for David Duke's 1996 campaign for U.S. Senate.
There are, obviously, some names in there that I recognize.
A donation from longtime Klan lawyer Sam Dixon.
Salary payments made to a longtime Duke associate who happens to be the son-in-law of a guy who died in a shootout with U.S. Marshals.
Things like that.
Some of the names on those forms are stories I'll tell you eventually.
But as I was flipping idly through lists of small-dollar donors, one line caught my eye.
Not because it was a name that I recognized, but because of his profession.
Almost all of the people willingly putting their name on the record as a David Duke donor by 1996 were retired.
Line after line after line, donors list their occupation as retired.
And for those who did work, they were almost all self-employed.
But on August 27, 1996, David Duke's campaign received a $500 contribution from a New York City police officer.
1996 was a pretty long time ago at this point, so I was pretty sure there was no chance this man was still employed by the NYPD.
But I was curious if his fondness for David Duke ever caused any issues for him in his professional life.
That seems like a pretty safe bet, right?
But honestly, it might not make him that much more racist than any given NYPD officer chosen at random.
But it turns out that officer, Thomas Pappas, did something else in the mid-90s that almost ended up in front of the Supreme Court.
See, in the 90s, every year, the Mineola Auxiliary Police Department sent out mailings requesting donations to their "McGruff the Crime Dog" anti-drug program.
Most people throw that kind of thing away.
Some people will write a check and put it back in the pre-addressed return envelope to make a donation.
But every year, one envelope came back to that volunteer organization stuffed with anti-Semitic cartoons, pamphlets with racist conspiracy theories, And materials published by a group called the National Association for the Advancement of White People.
And by 1997, the volunteer organization receiving these mailings went to the police.
After years of getting these hateful mailings, they'd hired a company to encode the reply envelopes.
If someone mailed back one of the smaller donation envelopes, they'd be able to tell exactly where the original mailing had been sent.
So when the racist flyers showed up that year, They used the tracking code to connect that envelope to a particular P.O. box.
And when they went to the police, they were able to determine that that P.O. box was registered to a New York City police officer.
And so to test their theory, the Nassau County Police sent a fake letter to that P.O. box soliciting donations for a charitable cause.
And he took the bait.
He stuffed the reply envelope with racist flyers and mailed it back.
Nassau County then turned the investigation over to the NYPD's Internal Affairs Bureau, and they too tested the theory.
They mailed Thomas Pappas a letter asking for donations to a charitable organization, and he returned the envelope full of anti-Semitic cartoons.
And when he was confronted with this evidence, he did eventually admit that he'd done it.
He tried to be casual about it.
At first, he said it was just a hobby, and then it didn't mean anything.
And then later in the same interview, he said it was a form of protest because he was, quote, tired of being shaken down by charitable organizations.
And it turned out that while it had just been the one organization who finally figured out where the mailings were coming from and went to the police, he'd done this hundreds of times over the years to countless organizations.
After he admitted to the mailings in 1998, The New York Times reported that he was probably going to be allowed to retire with his pension.
But after a full investigation and disciplinary hearing and a lot of public outcry, he was found guilty of prohibited conduct and fired.
So he sued.
He filed a lawsuit in federal court, naming New York City, the police commissioner, and the mayor as defendants.
Which, in 2000, makes the case citation Pappas v.
Giuliani.
Pappas claimed he'd been unfairly terminated in retaliation for engaging in protected First Amendment conduct.
The Southern District of New York disagreed.
Pappas was absolutely within his right to mail people racist pamphlets, but that's not the issue here.
He wasn't criminally charged for it.
And there is significant case law that allows government employers to take disciplinary action when it comes to speech by public employees.
when there is a legitimate government interest in promoting the efficiency of the public services it performs through its employees.
Pappas may have had a better case here if he'd been engaged in speech that looked more like protest, if he'd made any attempt to engage in public discourse, or if he'd mailed the flyers to parties who were engaged in public activity on the issues he claimed he was protesting.
But he was just mailing garbage to any random organization unlucky enough to have sent him a pre-addressed envelope.
Quoting from the opinion, This claim defies reason and the record.
Although the First Amendment's protection does not turn on the effectiveness of a speaker's media strategy, Mr. Pappas' purported strategy for addressing the matter of public concern is so plainly unreasonable, it belies his claim that addressing matters of public concern was ever his intention.
So his speech was, as the court wrote, of relatively low First Amendment value.
And then on the other side of the scale, there's the very real concern of the government employer that his activity could disrupt government business.
His activities had become a matter of real public concern.
People were very worried that this cop hated Jews and black people.
So they can't fire him for being racist, for having racist ideas.
They can't fire him for what's in his heart.
But they fired him for being racist in public, out loud, and in a way that was damaging to the department's reputation and mission.
And look.
Just for the sake of this legal argument, try not to laugh at the idea of the NYPD having a reputation that could be tarnished like this, okay?
So after he lost this lawsuit, he appealed the decision up to the Second Circuit Court of Appeals in 2002, and they affirmed the lower court's decision with one judge on that three-judge panel dissenting.
And the dissent makes...
A number of arguments.
You know, he wasn't a supervisor.
He did this on his own time.
He didn't do it at work.
He did it privately.
He did it anonymously.
And most alarmingly, the dissent argues that if the department had never disciplined him in the first place, the public trust wouldn't have been damaged because no one ever would have known that it was a cop doing this.
That the department itself is responsible for the damage to its own reputation because...
I guess the proper course of action here would have been to cover up this policy violation.
The case was back in the news a few years later when that dissenting judge, Sonia Sotomayor, was nominated to the Supreme Court.
I found several op-eds citing this dissent as proof that she was a fair-minded defender of free speech, and these were largely attempts to counter right-wing attacks on her nomination.
But if you look back at the majority opinion in this case, her colleagues called her dissent a misunderstanding of the law and seriously misguided.
As Oliver Wendell Holmes said in 1892, a policeman may have a constitutional right to talk politics, but he has no constitutional right to be a policeman.
So, it turns out police departments really can fire a cop.
for being extremely racist in his private life.
They just usually don't want to.
We're Little Guys is a production of Cool Zone Media and iHeartRadio.
It's research written and recorded by me, Molly Conger.
Our executive producers are Sophie Lichterman and Robert Evans.
The show was edited by the wildly talented Rory Gagan.
The theme music was composed by Brad Dickert.
You can email me at weirdlittleguyspodcast at gmail.com.
I will definitely read it, but I probably won't answer it.
You can exchange conspiracy theories about the show with other listeners on the Weird Little Guys subreddit.
Just don't post anything that's going to make you one of my weird little guys.
Just don't post anything that's going to make you one of my weird little guys.
Explore the winding halls of historical true crime with Holly Fry and Maria Tremarki, hosts of Criminalia, as they uncover curious cases from the past.
The legend of the highwayman suggests men dominated the field, but tell that to Lady Catherine Ferrars, known as the Wicked Lady, who terrorized England in the mid-1600s.
Her legend persists nearly 400 years after her death.
Highwaymen are in the hot seat this season.
Find more crime and cocktails on Criminalia.
Listen to Criminalia on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
A crime makes headlines.
People talk about it for a few days, then it disappears.
But for the people left behind, their story is just beginning.
But at night, we hear the garage opening, and my son hears it.
We freak out.
Honestly, I didn't tell my son this, but I thought that was it.
From the Exactly Right Network, this is The Knife.
Real stories of crime's ripple effects told by those who live them.
New episodes every Thursday.
Listen to The Knife on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
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