In January 1905, a Pendleton man took on a roulette wheel with a vow that he would either beat the game or walk away penniless.
The prominent Pendleton farmer, who was not named in the East Oregonian story, was a frequent gambler and was best known at winning at the roulette table. He began his run at the game at a similarly unnamed Main Street saloon at 11 a.m. on Jan. 30, drawing a large crowd to the gambling room to watch his battle. A limit of five chips, except for the center row of numbers on which he could bet $80 at a time, was the only rule.
The farmer’s fortunes varied up and down during the contest, at times having as much as $3,000 on the table, and at other times suffering a profound losing streak, but once he began he did not move from his seat nor even look up from the table. As the battle progressed, the crowds gathered in closer and players from other saloons left their games to watch his progress.
The game ended 14 hours later, at 1 a.m. After contributing $3,700 in gold pieces to the game coffers, the man rose from his chair, picked up his last two twenties and slipped them into his vest pocket, saying, “I still have enough left to start another game on.” He staggered a little as he left, though he had not touched a drop of liquor during the game.
The saloon owners figured they had made enough during the event to even up for the farmer’s past winnings at the game.
Gambling dens were common in Pendleton in the early 1900s, despite a move by law enforcement and the legislature to ban all vice from the state. A lawless faction even sought to retain the flavor of the Old West in early 1905 by proposing an amendment to the Pendleton city charter to set aside the state law regulating gambling, prostitution and other vices and give the matters into the hands of the city council. The proposed amendment was submitted anonymously and was not endorsed by any members of the Pendleton citizenry. It was suggested that the amendment would give the saloon owners, gamblers and other rough elements a chance to stack the election of a mayor and city council that would open the city to vice, in spite of the wishes of the moral element of Pendleton. A similar amendment was proposed in Freewater, and Portland and Astoria also reported similar proposals.