Both O.K. Grimstad and Rockwood Brown loved the sport of boxing and had actually discussed the possibility of holding such a match in Billings. As Billing’s Commercial Club members, each man thought that a regulated sport like boxing might also work well to benefit the city’s promotion.
Two years previously, Brown had witnessed a Jack Demspey fight in Jersey City and had given The Billings Gazette an extensive interview following the fight. He commented, “I do not believe that there is anyone who can beat Dempsey unless they wait until he is so old he can’t fight.”
Both men enthusiastically traveled to Shelby to watch and gauge the outdoor fight as a possible model for a future Billings promotion.
The fight was a fifteen-rounder won unanimously by Dempsey. But it was, unfortunately, a huge financial bust. Few people paid to take the train out to rural Montana.
From the East Coast, it still took a week to get there and a week to return.