Dempsey's brother Bernie was largely responsible for his success, both then and up until he was champion. Besides giving his brother boxing tips, he gave him a taste of what real fighting was all about. After the family moved to Uncompahgre in 1907, Bernie let his brother tag along when he went looking for saloon fights in neighboring towns. Dempsey was fascinated by what he saw. The ropes were usually made out of clothesline, and the gloves, if any were available, were often crusty with dried blood. He loved watching Bernie fight, even though he sometimes took awful beatings. Witnessing those fights confirmed that he wanted to be a fighter, just like his brother.
WHEN THE FAMILY MOVED to Montrose in 1909, Dempsey started training seriously with his brother. Bernie had told him stories of fights being stopped because of simple cuts and instructed him to bathe his face and hands in beef brine to toughen the skin, something he continued to do throughout his career. To strengthen his jaw, Bernie had him chew tree gum. To develop speed, he skipped rope and chased horses up and down Main Street. Before long, he was ready for his first prize fight. He was thirteen. The fight was against Tommy Pitts, one of two boys Dempsey regularly squared off with. The prize was two chickens. "I won the fight," Dempsey later said, "but you'd never know it if you'd seen my face." He would also win his first professional fight several years later.
After graduating from the eighth grade in Provo, Utah, Dempsey returned to Montrose to start his boxing career. His first professional fight took place at the Moose Hall against Fred Wood, The Fighting Blacksmith. Dempsey fought under the name, Kid Blackie. Bernie had been fighting as Jack Dempsey, after the great middleweight of the eighteen eighties and nineties, and suggested that his brother use a ring name like Kid Dawson or Kid McCoy. Dempsey decided on Kid Blackie because of his dark hair and complexion.
AFTER THE FIGHT was set, Dempsey sold tickets on the street for twenty-five cents apiece. He trained for the fight in an old shed in back of Fred's father's blacksmith shop. He built a cage inside the shed, roughly the size of a ring, but only four feet high, forcing him to shadow box in a crouched position, which he hoped would make him harder to hit and enable him to deliver harder punches.