He was listed as one of the twelve most underestimated gunmen of the Old West in the book "Deadly Dozen", written by Robert K. DeArment.
While working in mining camps in the US, he became a member of a revolutionary group called the Fenian Brotherhood, intent on overthrowing the English control in Ireland.
The group was victorious in the 1866 Battle of Ridgeway, but ultimately the movement faltered when the United States intervened.
Desmond was part of a force led by Fenian General John O'Neil that invaded Canada from Buffalo, New York.
A few months later he had arrived in Kit Carson, Colorado, a town that had almost overnight exploded into a population of over 1,500 people.
By 1870, Smith had gone on to become the Marshal of Abilene, Kansas, where he would ultimately be killed in a gunfight, after which he was replaced by Wild Bill Hickok.
Not long afterward he began working as a deputy for the Pueblo County, Colorado Sheriffs Office.
Desmond and Pueblo County Sheriff Henley Price were arrested for the assault, and charged with numerous counts of murder.
On July 1, 1881, Desmond boarded a train bound for Denver, Colorado, to transport Burton into the custody of Federal authorities.
Upon reaching Denver, Desmond learned that his suspect was actually Hamilton "Ham" White, the most wanted stagecoach robber in the nation, with an outstanding reward on him for $1,200.
Back in Pueblo, on February 11, 1882, Desmond was summoned to Union Station where several African American men and women complained that a local police officer, John T. "Jack" O'Connor had abused them.
Desmond located O'Connor, who was intoxicated, and the two became involved in an argument witnessed by Patrolman Rube Gutshall.
Gutshall, Deputy Dave Abrams, and Pinkerton Detective Bill Richardson then wrestled O'Connor into custody.
This led to a bitter feud between the police department and the sheriff's office, and eventually the city council fired Desmond over the affair, and reinstated Gutshall and O'Connor.
Desmond had ample support from citizen groups following this incident to run for the office of mayor, but he declined.
He hired several former officers who had supported him during the earlier feud with the police department officials and the city, including Bill Richardson.
He then began working as an independent force inside the town, something that was fiercely opposed by Marshal Henry Jameson and his department.
Over the next few months, however, the detective agency made more arrests than the city police department, capturing several noted thieves and one murderer.
By 1885 he had remarried, to a woman named Eva, and although he continued to find himself involved in numerous bar brawls, the couple seemingly had a solid marriage.
However, half an hour later Desmond returned, obviously believing that Owenby would no longer be there, and in the company of his wife Eva.
Officers Caldwell and O'Kelly responded, arresting Owenby and calling for medical assistance for Desmond.
Todd had a reputation also as a brawler, and had spent time in jail in Pueblo for shooting and wounding businessman Bert Reynolds.
On the night of February 28, 1890, Desmond met Todd and another man, Tom O'Neil, inside the Little King Saloon.