Property Cadillac Jack's®

Celebrate the grand opening of Wagers Sportsbook & Grille inside Cadillac Jack’s® Gaming Resort November 6-8 with can’t miss specials.

Bring your best Halloween costume to Caddy’s Costume Contest on October 31 and compete for $3,000 in cash and prizes at Cadillac Jack’s®.

Join us at Cadillac Jack’s® in Deadwood for a Dueling Pianos show packed with live music, comedy, and nonstop entertainment.

Qualify through participating radio stations to compete for $20,000 in cash & prizes at Triple Play Showdown at Cadillac Jack’s®.

Calling all tattoo artists and enthusiasts, join Cadillac Jack’s® for our 4th Annual Tattoo Convention! Featuring the most talented artists!

Goodbye 2026, Hello 2027! Ring in the New Year with Cadillac Jack’s® this year with promotions, dining options, and an exciting gaming floor.

Get ready for the Monster Stacks Poker Tournament at Cadillac Jack’s®—packed with big stacks, high stakes, and nonstop action!