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

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.



An experienced attendant with a friendly and upbeat approach that will make you feel welcome at The Warden's Casino! Kayla works the evening shift and enjoys helping to make your night out fun and entertaining!

The Warden's Casino - Anne


Anne is the newest face of The Warden's Casino replacing Tammie as our on-site manager. (Don't worry! Tammie is still with us in a new position.) Anne comes to us with an excellent resume for outstanding customer service. She is attentive and eager to please so you can be certain she will ensure your visit is pleasant. She will be working the day shift and looks forward to meeting you!

The Warden's Casino - Mike


He's baaack! You may remember Mike from his days working for the previous owner. Mike is an experienced attendant who excels at making your trip to The Warden's Casino as enjoyable as it can be. He won't interrupt you if you are into your game, but is happy to chat if you are in the mood. Mike works days and weekends.