8 AM to 2 AM 7 Days a Week

1414 4th Avenue N
Billings, MT 59101

About Us

Owners of The Warden’s Casino

Jessie and Dennis Benson, owners of The Warden’s Casino, moved from Minnesota after years of service as prison wardens. Jessica Benson, standing 5 ft. tall, started out as a typist at a Minnesota state prison and worked her way up to the top as warden at state’s maximum security prison. Dennis Benson was also a warden at one of Minnesota’s state prisons, and retired as one of the top correctional officers at the Minnesota Department of Corrections. The Warden’s Casino is not only beautiful and clean, but you’ll get a chance to see neat prison artifacts like keys, prison locks, and old leg irons.

The Warden's Casino - Owners

Dennis and Jessie are former prison wardens and the owners of The Warden’s Casino on 4th Ave N. They have made a home in Billings along with their business and are proud grandparents. They love to tell a funny story or two about their prison days.

Meet the Staff



Kassi is our manager and has worked for The Wardens Casino for a few years now. She is a reliable, sweet, kind, hardworking mother of a little boy. Her interests are enjoying a good book, spending time with family and loves to be doing anything outdoors. Come down and say hello to our rock-star team member!



Meet Monica! She will be working evenings. Her hobbies are reading a good book, taking nice long walks with her family, and watching movies with her kiddos! She is so sweet, and we are excited to welcome her to our team. Come say hello!


Jess J.

In her spare time, you can find Jess spending time with her family. She enjoys shooting and traveling Montana country. She also enjoys time at home cooking and reading. Jess will take good care you at The Warden’s Casino!



Ashleigh is the newest member of The Wardens Team coming from Colorado. She enjoys traveling, reading a good book, or hitting up the gym in her spare time. She is friendly and fun to talk to! Ashleigh works evenings and is a great attendant. Stop by and say Hi!