All Episodes

September 10, 2025 9 mins

Old Chile introduces us to Roy—the flashiest, fiercest, most unforgettable character to ever disco-dance into danger. From silk shirts and diamond-studded Rolexes to wartime poker rings and after-hours shootouts, Roy wasn’t just a man—he was a walking firecracker in gator loafers. In this explosive tale (literally), Chile recounts how a would-be robbery turned into a foot-blasting lesson from one bad old man who was not in the mood. Brace yourself—this one’s loud, legendary, and 100% Roy.

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
It's old chili coming back at you, and I've got one.
I've got one for you today about the most colorful
human being I ever had the pleasure of becoming friends with.
And this is a story about about my pal Roy.
And some of you will know who he is, but

(00:22):
what about ninety nine point nine percent of you will not?
But anyway, here it goes. I hope you enjoy it.
Fire exploded from the barrel of the nickel plated twenty
five caliber pistol. A deviously home crafted slug followed the fire.

(00:45):
The lead projectile split open exactly along crosscuts made in
it by my pal Roy. The destruction of flesh, bone,
and skin happened instantaneously. A cloud of gunpowder mixed with
a fog of blood, bone and skin fragments floated over

(01:07):
the scene. Now we're going to back up in time
five years to nineteen seventy one. You know, I look
quite nice, I thought. In my first day of work
at the Tidle Insurance Company in downtown Houston. It was July,
but I wore an ensemble of petrol chemical fabric and

(01:28):
dying on as double net. My duds consisted of navy
blue blazer over white dress shirt with blue butterflies on it,
crimson paisley tie that spread age inches at the bottom
almost hid my shirt. My slacks were black and white

(01:48):
hound's toothprint with blue and red saddle Oxford's peeking out
below the well the bell bottomed cuff. I looked like
so many other young hipster of the day, but I
looked very different from the lawyers in accountants that occupied
the offices of the title company. I enjoyed the entry

(02:10):
level position of copy shooter. I read filing information from
a list, pulled microfilm, and photo copied requested documents for
the lawyers to examine the titled real Estate my first
job on herd. On the I heard a man who
sounded a lot like an old movie star named Edward g. Robinson.

(02:36):
This guy stood about five feet five inches tall, had
white hair, shiny alligator loafers, silk sport coat and shirt,
gaberdine slacks, a fat, big cigar in his mouth, and
a gold rolex. The roles had a diamond bezzle surrounded

(02:56):
a lapist dial that bore his name out of the
Hallmark trademark rolex. The watch bend supported a thick nugget
designed with more diamonds. His demeanor spoke of authority and impatient.
I asked a fellow shooter who was that guy. He said,

(03:20):
that's Roy B and he owns this place, and when
he's around, you better be busy and quiet. Well I
got the message now, Roy. I later found that I
grew up on a tenant farm in Arkansas during the Depression.
His father expected him to help on the farm, but

(03:43):
he hated farm work and found his love and schoolwork.
He told me later that he had to fistfight his
dad to go to school. He later lied about his
age to enter the army for duty in the Second
World War. He escaped farm to fight on different fields

(04:04):
in different battles. During the war, Roy fought on the
European Front. Seventeen years old, full of life and ideas,
He ran poker games a couple prostitutes through the ranks
of the Allied Army. He sold the leads in uniform
everything from cigarettes to silk holes. The money he earned

(04:27):
paid for his tuition to law school. After the war.
Roy appreciated dedication with hard work, and maybe I delivered.
I arrived at the Title company office before six thirty
in the morning and I worked until at least seven
pm in the evening. That is six days week of

(04:49):
twelve hour almost days. I had not been on the
job long when I saw an opportunity to eat introduced
myself to him. He said he'd been watching me work,
and aside from dressing like an East Texas clap doctor,
I was acceptable. Fast forward to nineteen seventy three, Roy

(05:12):
and I became more close. I continued to work hard
and enjoyed promotions that came along quickly. I managed the
department in which I had started my work in nineteen
seventy three had also brought a divorce into Roy's life.
A beautiful townhouse near downtown became his bachelor pad. You

(05:36):
could find him nightly at the Penthouse club of the
Warwick Hotel on Main Street, holding court and disco dancing
with the goddesses, his new found hobby. The club closed
at two o'clock in the morning, and Roy was there
to see most last call for drinks. One morning, following

(05:59):
night of drinking and dancing, I greeted Roy at the
front door of the office building. Ay as hell's it going,
he replied, Come into my office, and I asked him
to tell you about last night's excitement. I eagerly followed
him into the elevator and exited into a suite of
offices on the fourth floor. Before he reached his desk,

(06:24):
he started, well, I left the water Wick about two
this morning and drove into my driveway. I opened the
automat gate and saw two men coming towards my car
from my house. I knew this would be trouble, so
I reached in my glove box and got my little
pistol out. I opened my car door and stepped out.

(06:49):
These two were less than fifteen feet from my car. Now, well,
may I help you two sports. Then one of the
men replied, we're going to rob you. Old man. Roy replied,
I had this little pistol between you and me, and
you had better know I all use it. One of

(07:12):
the guys said, you don't have the guts to use
that thing, old man. That was just before the gun discharged.
As described, the pistol fired, The bullet hit the target
in one of the burglar's ankles. The shop blew the
guy's foot ten feet from his leg. He went down

(07:35):
on the pavement, screaming in pain. His blood gush from
the amputation. I want you to kind of just to know
that this is a lucky night. I had been to
a wonderful bartie at the war wicking. I'm pretty tired.
I'm too tired to kill you both, and too tired

(07:56):
to stay up the rest of the night talking to
the damned police. I suggest that you take your friend up,
get his foot, and drag him away off my property.
Oh and please tell you old hoodlum pals down there
that there's this crazy old man who lives here and

(08:19):
he will cheerfully kill any son of a bitch who's
trying to steal anything. Now, good night, gentlemen. That's Roy.
And I'm going to follow up down the line with
two or three more little vignettes like this describing some
of the stuff that Roy did and he had. This

(08:44):
is this chili signing off, and I want you to
chill out, have peace, and for God's sake, watch those intersections.
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.