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Trial of Kid Trailer, Ky Matthews meant 'end of organized rustling' in the Dakotas

Posted 2/17/23 (Fri)

By Jayme L. Job, Prairie Public

February 15, 2023 

MINOT — The trials of horse rustlers Kid Trailer and Ky Matthews continued on this date in 1910 in Minot. Four famed lawmen in attendance marked the occasion as the “end of organized rustling in the northwest.”

Kid Trailer, alias Jack Winnefield, formerly worked in the Jones-Carlyle rustling gang. He had a reputation as an excellent fiddle player, but earned his nickname from his frequent attachments to known outlaws.

The Jones-Carlyle gang would run cattle and horses north to Canada, changing the brands and operating an extensive trail system of outposts and hide-outs. By 1904, the Jones-Carlyle gang had broken up, with the death of both Jones and Carlyle. Kid Trailer took up on a homestead near Stady, North Dakota, along with his pal Joe Knapp.

Sheriff Olson of Williams County was credited with capturing the last of these great rustlers, Kid Trailer — although it could be argued that Sheriff Olson had less to do with Kid Trailer’s capture than Kid Trailer’s own pal, Joe Knapp.

Knapp heard of the $800 reward on Trailer’s head and decided to turn him in. When Trailer was sentenced to twenty years in the North Dakota State Penitentiary, he stated, “Take good care of my buckskin horse until I get out, and when I do, Joe will be a dead man!”

Trailer was paroled a few years early, and took up smuggling whiskey from Canada. It is rumored that he died in Arizona in the 1970s.

“Dakota Datebook” is a radio series from Prairie Public in partnership with the State Historical Society of North Dakota and with funding from Humanities North Dakota. It is edited for presentation on Forum Communication Co. sites by Jeremy Fugleberg, editor of The Vault. See all the Dakota Datebooks at,  subscribe to the “Dakota Datebook” podcast, or buy the Dakota Datebook book at