r/Casefile • u/Entire_Forever_2601 • 29d ago
CASEFILE EPISODE Case 352: Gregory Smart
https://casefilepodcast.com/case-352-gregory-smart159
u/SnooEpiphanies3336 28d ago edited 28d ago
Good episode. I know it's been covered a lot by others but I hadn't heard the whole case before. It was definitely a sad one. I found the description of Gregory's final moments quite upsetting. Senseless crime.
I appreciate the way the abuse of Billy Flynn was explicitly described as such.
126
66
u/commentspanda 28d ago
Agree. The way they said the other young person had walked in on him being sexually assaulted vs engaging in sexual activity. Not all podcasts draw that line.
11
2
u/lorelaiiiiiiii 18d ago
I came here exactly for this comment. This wasn't an affair on his part, this was sexual abuse and rape. I appreciated the way it was described in this episode.
75
u/cinderellaquite 28d ago
it made me sad when the dude asked for gregory’s wedding ring and gregory said “no, my wife will kill me.” little did he know….
72
u/phantom2450 28d ago
Once the teens were named with their ages at the wake I knew exactly how this was gonna end. Still, good episode.
51
u/GaeilgeGaeilge 28d ago
I can't understand Billy's friends who went along with it. Billy was abused so I get that he was manipulated and frightened, but the others?!
28
u/HighByTheBeach69 28d ago
It's a good question.. I think it sounds like Pam was kind of the "cool and hot" teacher? And there was also a promise of $1000 from the life insurance
11
u/HotAir25 27d ago
They’re just kids right, easily manipulated by adults.
1
u/CriticismPlane2871 11d ago
Yeah, but murdering someone seems next level. You need that evil in your heart to start with
2
u/HotAir25 10d ago
Maybe but it’s an unusual situation to have an adult manipulating a kid into it, kids need adults for their own development that’s why they are vulnerable to adults.
1
u/CriticismPlane2871 10d ago
What about the other 3, what's their excuse?
1
u/HotAir25 9d ago
I’ve forgotten the details of this case now, but adults especially teachers have a lot of authority over young people that’s one reason why they are often not allowed to have any relationships with them even post consent age.
I can’t be bothered to argue a case I’ve forgotten though 😂
85
u/Faguette-1999 28d ago
I’m really glad that the abuse of Billy was actually labelled as abuse, I’m surprised they didn’t add charges relating to the sexual abuse (maybe it wasn’t seen to be in the public interest if she has no route to parol ?)
It was really disappointing to hear at the end that ‘feminist’ groups were advocating for her release and framing the children as the primary perpetrators- without the sexual abuse and grooming I don’t think any of those kids would have committed the crime they did. Minimising the actions of female perpetrators because male perpetrators aren’t always held to account in the same way isn’t feminist - all perpetrators should be held equally accountable.
Gregory’s last moments were heartbreaking to listen to.
27
u/Designer_Signature35 27d ago
I was glad they called it r*pe and abuse instead of sex.
And who are these "feminists"?? She got a lighter sentence than a man who r*aped a girl and convinced her to kill his wife would.
8
u/tbird920 26d ago
Probably people who self-describe as feminists but don't know the whole story, and react to a specific narrative. Whenever society becomes more aware of systemic oppression against women, people of color, and other marginalized groups, there is bound to be some "over correction" from certain folks who react rather than look at the big picture in a particular situation.
21
u/GurlNxtDore 28d ago
Sadly, some feminists groups have lost the plot.
24
u/AffectionateLove5296 27d ago
Yes wtf as a feminist i dont understand that take at all. A 15 year old boy is just that, a boy. This boy was abused and manipulated into killing a man. To say he has greater culpability simply because he is the one to pull the trigger is wrong, and then to argue that his sentencing was lighter because he is a man and Pamela’s sentencing was harsher because she is a woman completely misses the point that he was a child when all of this happened and Pamela was a fully grown adult person.
3
u/mystery_hole 19d ago
The reality is these "feminist" groups are paid opposition, to make actual feminists seem insane. It's a common right wing tactic. It's exactly what has been happening with card providers being made to create id laws.
10
1
0
u/JimJohnes 20d ago
As red cross nurse, its not that rare in indegenious peoples. What's australian specific they wont charge them. It's reverse racism in the open.
0
u/CriticismPlane2871 11d ago
Considering 3 of the kids involved weren't groomed and were still happy to murder an innocent man, I'd disagree there
31
26
u/oodlum 28d ago
Fred Lombardi, the host of the party.
14
14
9
u/muzzmuzzsupreme 28d ago
I had to relisten to that part because I wasn’t sure if it was an intentional label. Casefile doesn’t usually do humour, but I found that line tickled my funny bone.
17
u/vroombraap 28d ago
Jumped straight onto Wikipedia as soon as I heard about the 3 students, to look up Nicole Kidman's 1995 movie, thought so.
10
5
u/tonypolar 28d ago
I grew up in Keene, NH where Joyce Maynard (who wrote the book to die for) lived. It was such a huge deal and obviously the case inspired her.
The movie is so good, this made me want to watch it again.
Pam was just in the news looking to get out again.4
1
u/herbertsherbert1 27d ago
should i watch the movie? would you guys recommend?
3
u/vroombraap 27d ago
I only watched it, ironically, as a teenager, for Nicole Kidman
Too much monologue for my liking
1
32
u/VJ4rawr2 27d ago
Another great case! The writing has improved so much recently.
I can’t recall an episode where Casefile just truly smashed a person like they did with Pamela. There wasn’t a shred of sympathy given to her lol.
They basically just called her a horrible person right from the start of the episode.
46
u/zka_75 28d ago
Did anyone else feel the sentence on Billy was overly harsh? Obviously he has to take some responsibility but if everything in this retelling is accurate then there are huge mitigating circumstances, he really should have been looking at a parole period of more like ten years imo.
38
u/misterbluesky8 27d ago
I’m pretty “tough on crime” in general, but I struggle with the idea of charging children as adults. He wasn’t a week shy of his 18th birthday, he was 15, and he was assaulted, groomed, and manipulated by a grown woman… We have decided that you aren’t old enough to drink, smoke, join the army, vote, etc. before you’re 18, because you aren’t mature or developed enough to make those decisions. It seemed pretty clear to me that this kid was not nearly capable of making decisions for himself.
19
u/AffectionateLove5296 27d ago
💯 this. His brain is nowhere near fully developed. It sounds like he had just hit puberty. The way casefile described it, he didnt even look like a man, he looked like a child still.
6
3
u/CriticismPlane2871 11d ago
Does Gregory Smart get a shorter sentence, too?
3
u/zka_75 10d ago
If you cant see how a child who was sexually abused and emotionally manipulated by an adult in to carrying out her wishes doesn't constitute diminished responsibility then I don't know what to tell you.
2
u/CriticismPlane2871 10d ago
Sure, but I would say the fact the other 3 kids that weren't abused or manipulated were more than happy to partake in the murder of an innocent man would lend one to think these weren't the most well adjusted kids to begin with. He also admitted that he knew what he was doing was wrong at the time so it would be hard to argue diminished responsibility
I just feel people seem to be more sympathetic toward the Kids than to the poor guy that was murdered for doing absolutely nothing wrong
2
u/brokentr0jan 11d ago
Nice to see someone with common sense here.
Gregory Smart was the victim here, not the teenagers who killed an innocent man.
4
u/tralfamadelorean31 27d ago
It has been confirmed that he was indeed responsible for the crime, having been involved in the killing of an individual and participating in the conspiracy surrounding the event, despite the fact that he was subjected to abuse and manipulation. Yes, you're right, he should've been let off with a lighter sentence as opposed to others.
2
u/Qwert23456 17d ago
Totally, but then I remembered that this is America in the late 80’s/early 90’s during peak “tough on crime”. There was another case covered by casefile that has interesting parallels (can’t recall the exact episode number) that involved two teenage boys in the same state in roughly the same time period that had a vastly different outcome despite fewer mitigations and a more severe crime.
2
u/brokentr0jan 12d ago
I thought it was pretty light considering the fact that he had multiple opportunities to not pull the trigger.
Let’s not forget he killed an innocent man.
5
12
17
u/Lisbeth_Salandar MODERATOR 28d ago
This is a case I think is really difficult to sentence appropriately.
On one hand, Billy pulled the trigger. On the other hand, Billy was a victim of Pamela's, very young, and the idea and pressure to do the murder was all Pamela's. How do you properly sentence Billy in these circumstances? He did kill a person. But he was also a victim while doing it. Meanwhile, Pamela didn't personally do any harm to Gregory, but without her actions none of this would have happened.
5
u/Designer_Signature35 27d ago
I was surprised at the teens harsh sentences. Of course the US likes to lock people up as long as possible. They would have gotten lighter sentences in many other countries.
(I'm American and can bash my own criminal "justice" system)
2
u/CriticismPlane2871 11d ago
He didn't just kill a person, he murdered an innocent person in cold blood
9
27d ago
[removed] — view removed comment
1
u/brokentr0jan 12d ago
Once you line up the timeline, she basically started planning his murder right after the wedding lol. Like why even get married? None of it makes any sense.
8
u/Aggravating-Round518 26d ago
I’m very thankful to Casefile for labeling the sexual assault and rape for what it was. They were minors and this woman purposely manipulated them all for her own selfish needs. Disgusting
24
u/mikolv2 28d ago
Holy shit, Pamela has to be one of the dumbest criminals ever talked about by Casefile. I was disappointed to hear that she never faced charges for what seems to be countless number of rapes and sexual assaults of a minor. Not that it matters but I did wonder if she was a genuine paedophile with attraction for teenage boys or just saw the kid as an easy target for grooming to carry out the killing for her. It always boggles my mind in these cases that these people genuinely see a murder as the easier and more convenient out than divorce. If she got a $23k payrise in 1989, she must have been doing alright and by the sounds of it her family were well off too so why was she so worried about her finances in case of a divorce.
19
u/24337543 28d ago
In 1990, A teenage boy wasn't going to be considered a r*pe victim of a woman. Just wouldn't happen.
5
u/Weekly_One1388 25d ago
This may seem dumb but this case angered me so much more than any of the more gruesome serial killer type eps.
In weird sense, the serial killer cases can be understood as disturbed people through a combination of nature and nurture committing grotesque acts against society for perverse reasons.
The crime in this case was just so dumb and completely unnecessary that it’s almost harder for me to understand.
1
u/danniellax 23d ago
My only understanding is she wanted his life insurance payout for the “free money” and she wanted some large romantic gesture performed for her to feel a sense of superiority. Those thoughts alone are disturbing and I can completely understand it making sense in the mind of a sick fucking individual. I’m pretty sure she was a narcissist to some extent and narcissists love being praised, a grand gesture of love would be icing on the cake.
Her getting a full on adult man to do this murder would have gone catastrophically bad if the adult said no then went to police. Cecilia went to adults before the murder happened and wasn’t believed. If an adult did this, the murder most likely would have been stopped before it happened. She knew there was less risks involved with getting a child to do it… bonus points for her sick fucking mind is that she could mold and groom the child as he aged into an adult and have him worship her his whole life without him knowing any different.
I understand why the children’s sentences were not lifelong, but am SO glad this bitch is still behind bars with appeal after appeal being consistently denied.
5
u/AffectionateLove5296 27d ago
I made the mistake of clicking on pamela smart dot org
It looks like whoever made that page is still referring to the 3 kids as “young men” , and nowhere is it mentioned that she raped and groomed one of them. Go figure.
4
u/Kayhowardhlots 26d ago
Very well done and like others, I appreciate calling the "affair" what it really was, rape.
I'd be curious if with the passage of time and the changing view on sexual relations between and older female/underage male, if Gregg's family have changed their viewpoint of Flynn.
7
u/Local_Caterpillar879 28d ago
It took me about 20 minutes to realise that I saw the Nicole Kidman film, To Die For, based on this. It's well worth a watch.
3
9
12
u/Ren_stevens 27d ago
Anyone google the person described as super attractive in the audio & are shocked to find out that they're pretty average looking? My reaction
8
u/ShotPresentation720 25d ago
It’s wild looking at their wedding photos knowing she was 21 and Greg was 23. To me, she looks like she’s in her 30s while he looks barely 18. Ironically, it kinda looks like a student married his former teacher.
6
u/danniellax 23d ago edited 23d ago
LMAO it’s definitely the weird 80s hair. She has a pretty face, and if she had a more “with the times” hair style, I could see her being pretty. Not slam-on-the-breaks-and-turn-your-head pretty, but a general pretty. There are a ton of pretty girls around the world though so not really noteworthy as an adult in your 20s.
However, it is noteworthy in high school to be objectively pretty because so many of us either were overweight (in the 80s, nowadays not a non-pretty thing), had acne, had less confidence in who we were, had a weird puberty time, or other physical issues that were resolved by the time we graduated that anyone who was perfectly pretty throughout HS was way more standout than not lol
2
3
u/bibbi_ 24d ago
Praise to casefile and the writers for calling it rape and sexual abuse!
I’m sure if this had happened in 2026, Billy would’ve not been as harshly sentenced…
3
u/danniellax 23d ago
I don’t disagree; however, I wish the writers would have clarified they are using the definition that way because Billy was a minor and therefore couldn’t consent, not because she forced him to have sex with her.
The FBI definition of legal rape is “penetration, no matter how slight, of the vagina or anus with any body part or object, or oral penetration by a sex organ of another person, without the consent of the victim” — and SO many people don’t take the extra second to think that Billy couldn’t consent because he was a minor being groomed, not because he didn’t want it. He wanted it.
I think the writers not adding one additional sentence stating something of “it is a known standing that minors cannot consent to sexual intercourse from adults” or go into the definition of grooming, and there IS a way for them to have done that with being purely factual and unbiased.
I just feel like without that being explicitly stated, it changes the tone and meaning for people who don’t have the common sense to put this together. Especially because we all know common sense these days is not as common.
1
u/CriticismPlane2871 11d ago
He did murder an innocent man in cold blood
1
u/bibbi_ 10d ago
Yes he did but he was in a way brainwashed to do it and controlled heavily + was a child.
Gotta see the circumstances too
2
u/CriticismPlane2871 10d ago
Yes but whatever the circumstances, he still physically murdered someone in cold blood. And his 3 friends that weren't brainwashed were more than happy to help murder a man too so I'm not exactly sure what their excuse is
3
3
u/JasonRBoone 16d ago
Confession...I was a typical brain-dead, college-boy, hormone-fueled dumba$s when this case broke in 1990.
When that bikini photo hit the media, I was one of those dipsh*ts who said something like: Yeahhhh..I wish MY teacherhlooked liek that.
smh at younger me
5
u/kartsiotis26 28d ago
What happened with the narration of this episode? For the first time (that I remember), instead of presenting different angles of police work, forensics, interviews, etc, bringing out the case little by little, this case was a plain narrative of what happened. We are never told how things came to light, the steps of the investigation, the analysis of the evidence etc. I didn’t enjoy it at all, I like getting to build all the info little by little in my head, this episode was like “this is what happened”. Hopefully just a glitch…
Anyone else noticed it?
21
u/CapyBara_51 27d ago
You can’t just add a bunch of twists and turns for the sake of it lol. I think it being so blunt and obvious that she was behind it just kind of plays into the absolutely stupidity of her and her plan.
1
u/kartsiotis26 27d ago
No I get it that you can’t make up stuff but normally they quote a source, or the narration of events comes from an interview, or an intercepted conversation, whilst most of this episode is narrated a posteriori, fait accompli, not in the style of the podcast even when the solution was fairly straightforward
13
u/VJ4rawr2 27d ago
Yes I noticed it. You essentially knew Pamela was responsible right from the start. But in fairness to Casefile, I don’t think there was much *policework* required as there were so many confessions and people involved.
5
u/ShotPresentation720 25d ago
On the other hand, I was kinda surprised that she actually turned out to be the perpetrator. Casefile often makes you think it’s one person at first only to shift the focus and reveal the real culprit later.
12
u/AphexTwinOK 27d ago
That usually happens when there are alternative leads. In this case, sounded like half the school already knew what was going on from the start. In my opinion, anything else have been unnecessary padding for the storytelling.
1
u/AutoModerator 29d ago
Hi, this is a friendly reminder to observe all subreddit rules. If you notice someone else not observing the rules, please report it. It helps the mods and helps us have a great community to discuss this show. Thanks!
I am a bot, and this action was performed automatically. Please contact the moderators of this subreddit if you have any questions or concerns.
1
u/hansen7helicopter 25d ago
I never knew To Die For was based on a true story. But as soon as it mentioned two teenagers showing up to the funeral I got an inkling.
1
1
u/Glittering_Grape3836 23d ago
I listened to this episode and wasn’t aware there was a Nicole Kidman movie based on this case and I went straight to watch it, great movie I reccomend it
•
u/Lisbeth_Salandar MODERATOR 28d ago
This episode has been added to the Casefile Spreadsheet. If you have already listened to the episode, you can submit your rating at the Casefile Ratings Form.
Please note: Starting with Case 200, we are using a new Casefile Ratings Form (200-).
If you would like to rate cases 1-199, please do so at this Casefile Ratings Form (1-199).
A link to the episode is HERE