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Legends of the Old West

OUTLAWS Ep. 1 | “Doc Middleton”

Legends of the Old West

Black Barrel Media

Arts, History, Documentary, Society & Culture

4.83.7K Ratings

🗓️ 22 April 2026

⏱️ 34 minutes

🧾️ Download transcript

Summary

Before James Middleton Riley becomes known as Doc Middleton, he steals horses in Texas, escapes from prison in Texas, and escapes from jail in Nebraska. From his base in the Sandhills of northern Nebraska, Doc Middleton becomes the king of the horse thieves, and powerful forces join together to stop him. Later in life, Middleton becomes one of the legends of the West who joins Buffalo Bill Cody’s Wild West show.  Thanks to our sponsor, Quince! Use this link for Free Shipping and 365-day returns: Quince.com/lotow Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial. On YouTube, subscribe to LEGENDS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

The 19-year-old kid who walked into the Texas State Prison at Huntsville in 1870 was probably booked under the name James Middleton Riley.

0:23.1

If he were, there's no guarantee that that was his name. His first name might have been James, but it also might have been David.

0:29.3

His surname might have been Riley, and it might have come from his mother. It also might

0:33.9

have been Middleton, and it might have been neither of those. The most common story is that he was from Bastrop County, Texas, just east of Austin, and about two hours from Huntsville.

0:45.3

He also might have been from Mississippi.

0:47.3

He went to prison for something, obviously.

0:50.3

The two crimes that are most often cited are murder or horse theft.

0:55.3

Given the reputation he soon established and the earliest reference to the crime, it was

1:00.1

probably horse theft.

1:01.9

The story goes that he grew up in Bastrop County, Texas in the 1850s and 1860s, and he

1:07.9

stole his first horse when he was 14, sometime around 1865. He probably got caught for

1:14.8

stealing another one in 1870, and that was why he went to Huntsville, the towering fortress of a

1:20.6

prison that was nicknamed the Walls. Nine years later, infamous killer John Wesley Hardin would

1:26.8

be a guest at the facility.

1:28.7

Fifty years after that, a young thief from Dallas named Clyde Barrow would do six months at Huntsville before he was transferred to a prison farm.

1:37.3

The stint in prison interrupted his blossoming romance with a girl named Bonnie Parker.

1:42.6

In 1870, James Middleton Riley's prison sentence also interrupted a young romance.

1:48.7

He had married sometime before he was caught,

1:51.1

though virtually no information survives about his first wife.

1:55.0

The pattern of uncertainty continues with the year in which James decided

1:58.9

he was done doing time at Huntsville Prison.

2:07.3

In 1874 or 1875, James escaped Huntsville Prison. The rumor was that he somehow secured an

...

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