Gen. Cook had known Judd for years. In fact, his acquaintance with the newly made labor agent was so familiar that he had at one time taken a trip to Cañon City with the gentleman, at which time Mr. Judd had taken up his residence there for a period of one year for having appropriated a valuable horse and buggy belonging to a man named Veasey, living in Denver. This was only one of a long list of crimes of which he was guilty. He was a born thief, with a predisposition to horseflesh, and had done time in more than one penal institution for his thieving proclivities. His first exploit in this line, so far as known, consisted in stealing a wagon load of groceries and provisions from a freighter, who was hauling supplies from Topeka, Kan., to Fort Riley, at an early day before railroads were built through that section. The freighter's horses, which had been turned loose to graze at night, had strayed away, and while he was away hunting them, along came Judd, who lived near. There was no one about and he deemed it too good a chance to lose. Securing a team of his own he hitched to the wagon and drove off. The owner soon returned with his horses, and finding the wagon gone, set out to tracking the thief, whom he overtook after following him fourteen miles. Judd was convicted and sentenced to the state penitentiary at Leavenworth for three years.
After serving his term out, he decided that the boundless West afforded better opportunities for the exercise of his peculiar talents, and accordingly he came to Colorado early in the '70's.
When he came to Denver he showed the same fondness for other people's property. In 1871 he stole a horse and buckboard belonging to A. H. Jones, the liquor man, and in 1872 he stole a bicycle or velocipede from a man whose place of business was on Fifteenth street, next door to where Cella's restaurant was located. On both of these charges he was cleared by Gen. Sam Browne, who proved to the court that Judd was a kleptomaniac.
In 1873 he was arrested and sent to the county jail for one year (there being no state penitentiary at that time) for stealing a gold watch from a lady in West Denver, at what is known as the Williams house. He served this sentence and was discharged on February 28, 1874. In 1875 he was arrested, tried, convicted and sentenced to the state penitentiary for one year for stealing a horse and buggy and several hundred laths from a man named Veasey, as related above. The last crime he committed before breaking into politics so suddenly and so successfully, was the theft of a horse and buggy, the property of William Dingle, a Denver druggist, on the 14th of October, 1883, while the rig was standing in front of the store of the owner, in the Tabor block. He was seen by several parties to cross Cherry Creek bridge at Larimer street and drive out in the country. The matter was reported to the police, and Detective Mart Watrous was put to work on the case. He went to Judd's house and charged him with the crime. After denying it for a time, Judd finally confessed and went with Watrous, gathered up the property and turned it over to the detective.