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 has been promoted to manager. She is a sweet, kind, hard-working mom of a 2 year old boy. Her interests are enjoying a good book and spending time with family. Come down and say “Hi” to our newest rock-star team member.

The Warden's Casino - Tyson


Tyson is a long time attendant with The Warden’s Casino. Reliable and pleasant, he is more than happy to go the extra mile to help out and make sure your time with us is as comfortable as he can make it. Tyson works evenings so stop in and say hello!


Lyndsay H.

Lyndsay is our Assistant Manager. She has a background in Early Childhood, loves kids and has an 8 year old daughter who has a passion for dance. Lyndsay loves being outdoors in her home state of Montana and is an experienced Casino Attendant who loves getting to know customers and sharing a laugh or two. Lyndsay says “I can’t wait to serve you!”


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!