8 AM to 2 AM 7 Days a Week

1414 4th Avenue N
Billings, MT 59101

About Us

The Warden's Casino - Owners

Owners of The Warden’s Casino and The Warden’s Grand Casino

Jessie and Dennis Benson, owners of The Warden’s Casino and The Warden’s Grand 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.

Meet the Staff

tammie grubb

Tammie Grubb

Tammie is our on-site manager and has been in the business for 10 years, 8 of which have been in the same casino (from the previous owner to The Warden's). She missed the opportunity of being on the floor with all the staff and great customers so stop in and see her today!

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!



Lauryn is a social butterfly. She loves talking with people and trying to put a smile on their face. Her second home is the gym. She loves working out and likes to eat healthy. She finds fun projects to do at home with her two beautiful girls. She is a cosmetologist by trade, so in her free time it brings her great joy to make people feel beautiful.



She is new to the casino industry but has been in the customer service area for years. She is somewhat quiet but is quite the go-getter. Come on in to see just how wonderful she is for yourself.