How I Caught The Times Square Killer
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How does Jayson describe the shocking brick‑attack incident in Hell’s Kitchen?
He said, nah, nah, nah, nah, nah, nah, nah. I'm about to hit a white mother with this brick. Picks it up like a hammer strike. Bing! So I found a telephone booth, went in there, turned around in three circles, then came out. Dun dun dun dun! We flank a and the guy sat up and looked at me in the eye. He made like intense eye contact and he said. You witness him, bro. Yeah. And I said, damn. And then there's an article on him in GQ. I was born in Chicago, Illinois. I was born in a manger on the south side of Chicago, Illinois. No, I was born in uh on the south side of Chicago, Illinois.
What about your mom and dad?
Mom and dad. Mom was a uh bureaucrat, worked for Social Security. My father was a tax accountant. Uh very I I always call him Joe Jackson of income tax. Cause when I was 10 years old, he used to bring me into his office and taught me how to do taxes and navigate a 1040 and a schedule C and all these things. I'm surprised I don't have a nose job and a pet monkey. Cause I, you know, I wanted to go outside and play. He'd be like, Get in here and get a ten forty. So I was always in his office doing taxes. And my brother friends, they were, cause my brother's uh, he was nine years older than me. So his friends, they were at working age, they were working, and I would do their taxes when I was 10 years old. And they would always say, Jason, how can you get us uh some more money back?
And I found this little loophole. I eat the Michael Cox, the Matt Cox of me came out. But I found this um thing where if a Childs with you for more than six months of the year, you could claim head of the household. Right. And some of them did have. uh children. And they were able to claim head of the household and get a bigger tax refund. Yeah. Yeah. So Cadillac, you should thank me. Send me a check because they all spend their money on cars. You know how that South Side of Chicago in the 80s and 90s. No, it wasn't. I mean, it was cool if you're from there and you know there, right? If you know the area. But that's when gangster rap became popular. Right. So the street It never sounded cool to me, by the way.
No, it never community and you could go to the park and play basketball and the gangbangers in the neighborhood. If you were a school kid or an athlete, they really left you alone. They wouldn't let anyone mess with you. Like, hey, leave him alone. He's going to school. Leave him alone. He's playing ball. But then gangster rap came in and it started getting a little more vicious.
Right.
A little more vicious, you know. Everybody, uh guys, uh were start so there were the D boys that, you know, they were known in the neighborhood because they had money, they had cars, whatever. But then the killers started becoming popular. Like you know, so and so just Somebody was like, Oh, what? Really? Sound good. Yeah, yeah. And there was quite a few. They they they had a lot of status in the neighborhood for sure. Well not status. They were feared. They were very, very feared. Your parents had professional jobs. What are you living in this neighborhood for?
There was this gang in Chicago, huge gang, but they split into two. But our neighborhood, you know, they were still cool. Everyone went to school and they knew each other. Um But then they started beefing and I lived like right between the middle of the two gangs and It was horrible, man. It was horrible. You hear start hearing gunshots where you never never hear gunshots w never heard gunshots before. And it the violence just picked up around like Let me say eighty seven to about ninety one, it just picked up like I've never seen before.
Okay. But you're going to you're still While you're still in school.
I'm still in school, but so I wasn't in school in a neighborhood. I got I went to a language academy in Chicago. So I would get picked up by a school bus in front of the neighborhood school and bust out to this language academy in High Park, Chicago, where I would go in there and say, Guten Morgen, Kaiser Jason, spreckens he Deutsch. And I we learned German. I learned German from K through eighth grade.
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Chapters
8 chapters
1
How does Jayson describe the shocking brick‑attack incident in Hell’s Kitchen?
0:00–8:22
2
What early life experiences in Chicago shaped his view of taxes and hustling?
8:22–23:35
3
How did Jayson transition from modeling in New York to stand‑up comedy and the Kill Tony audition?
23:35–48:56
4
Why did Jayson decide to testify against the brick attacker and what legal charges followed?
48:56–1:01:41
5
What does the witness describe about the brutal murder and his reaction?
1:01:41–1:17:41
6
How does the legal process and plea negotiations unfold for the perpetrator?
1:17:41–1:33:49
7
Why does the narrator become paranoid about surveillance and discuss privacy?
1:33:49–1:51:29
8
What are the narrator’s thoughts on crime, fraud, and his future plans?
1:51:29–2:03:06
Speakers
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