To What Extent Can Someone 'Out' An Undercover Police Operation Without It Being A Crime?

Year ago, the Springfield (IL) Police Department did one of those stings where they round up people with outstanding warrants under the guise of telling them they’ve won some prize and all they have to do is collect it. The suspect comes inside thinking they’re getting a free flat screen, they confirm their identity, they’re put in cuffs.

Apparently the girlfriend of one of the suspects realized what was happening and started warning everyone within earshot what was going on. She was “detained,” according to an article I read about it the next day, but the piece didn’t say what happened to her afterwards.

Seems to be that the First Amendment is pretty clear here that she did nothing wrong. She was giving passer-by factual information, not yelling “Fire!” in a crowded theater or inciting insurrection.

So, is it a crime to disrupt undercover police operations (through just words, not actual subterfuge)? If I noticed an unmarked police car doing surveillance on my street and I walked out with a bullhorn and shouted “Cops! Whatever you’re doing, they’re onto you!” is that a crime? What if a teenager recognized a narc at their high school and outed him? What if a truck driver recognized a truck-stop “prostitute” doing undercover and started shadowing her, yelling to all of her johns that she’s a cop?

Something I thought of while ruminating on this.

Let’s say that the police are doing a prostitution sting. I recognize the bait hooker as an undercover cop, but I decide to have a little fun with her. I offer her $100 to sit quietly and listen to me talk for half an hour. No streetwalker in the country is going to turn that down, but an undercover bait hooker would miss out on half an hour’s worth of busing johns if she took the offer. But then again, she’d blow her cover if she refused.

If I tried to play this game at an undercover prostitution sting, would I see the inside of a jail cell?

In a more pedestrian context, people who warn drivers about speed traps can be arrested in some jurisdictions.

Might be obstruction of justice?

A couple of references that might inform the discussion:

A couple of years back, I went to a bar after work. I parked a block away (Pro-Life-Tip, always park a bit away from the bar). As I walked toward the bar, I passed an older car in which the driver was slouched down, with a great view of the bar.

I went into the bar and made an announcement. “There’s an old green beater parked across the road. The driver is a cop and is watching the bar.”

We all went outside. I pointed out the car, and while we were all standing there looking, it drove off. I was not arrested.

Nowadays they’ll just publicly shame you on Facebook, and ask why you don’t care about the children that will be run over by drunk drivers that the undercover cop would otherwise catch.

“Hindering Apprehension” is what Maine calls it, and it is a crime to warn someone of impending discovery or apprehension.

My guess is that the issue in this story is the the girlfriend is, in effect, harboring a fugitive. (A brief look suggests that it likely falls within the Illinois criminal code’s “concealing a fugitive” provision but it could be categorized in a number of ways). That is, she is actively hindering the apprehension of a wanted person by law enforcement. That’s generally illegal without posing first amendment issues.

ETA: I think the Illinois provision would be: “Every person not standing in the relation of husband, wife, parent, child, brother or sister to the offender, who, with intent to prevent the apprehension of the offender, conceals his knowledge that an offense has been committed or harbors, aids or conceals the offender, commits a Class 4 felony.”

Note that seeing the inside of a jail cell doesn’t require that you be doing anything actually illegal - if the cops believe you are interfering with their sting, it’s possible for them to arrest you on charges that won’t stick. They can hold you for something like 48-72 hours without filing any formal charges at all, and can easily come up with something to put on the arrest paperwork even if it isn’t good enough to put in front of a judge. You won’t be getting a jail sentence, but you’ll also be unable to interfere with their operations. And that’s assuming the undercover cop or people listening don’t interpret something you say as being code for a sex act, at which point they could bust you as part of the sting and let you sort out whether you really meant ‘listen to me talk’ in court later on.

Yes.

A person who knowingly resists or obstructs the performance by one known to the person to be a peace officer, firefighter, or correctional institution employee of any authorized act within his or her official capacity commits a Class A misdemeanor. - 720 ILCS 5/Art. 31 Interference with Public Officers

In the case the OP describes, the police (who are peace officers) were arresting people with outstanding warrants (which is an authorized act). The woman knew they were police officers and was warning people to stay away, which was obstructing the arrests.

Blockquote
Something I thought of while ruminating on this.
Let’s say that the police are doing a prostitution sting. I recognize the bait hooker as an undercover cop, but I decide to have a little fun with her. I offer her $100 to sit quietly and listen to me talk for half an hour. No streetwalker in the country is going to turn that down, but an undercover bait hooker would miss out on half an hour’s worth of busing johns if she took the offer. But then again, she’d blow her cover if she refused.
If I tried to play this game at an undercover prostitution sting, would I see the inside of a jail cell?
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Ultimately, it would come down to how sincere the police believed you were. Prostitutes do have johns that only want companionship. I imagine police officers working prostitution stings have strategies for dealing with this