Howard Crowley first died as a Marine on the beach at Iwo Jima. After becoming Immortal, and being mentored by Wayne Guthrie in the ways of The Immortals, Crowley's strategy was to settle in small towns, often as Sheriff, to search out and challenge local Immortals.
In 1992, Sheriff Crowley moved from Loveston to Steveston, Washington. He immediately targeted Immortal, Lucas Desiree, who had withdrawn from the Game, and lived in a cabin in the forest near the small town. On September 18, Crowley visited Desiree in his cabin, and beheaded him after a short fight. During the Quickening, a homeless Vietnam veteran, Leo Atkins, was passing through, and saw the bright light. Worried that the blame for Desiree's death would fall on him, Crowley seized the opportunity to arrest the transient for Desiree's murder.
Three days later, Duncan MacLeod, who was a friend of Desiree's, visited Atkins in jail, and realized that the man wasn't an Immortal, and definitely was not the killer. He later met Crowley and knew Crowley would be the logical killer. The Sheriff, however, used the town's men to herd MacLeod. At the same time, Sergeant Powell, who was investigating recent beheadings in Seacouver, came to Steveston to question Atkins.Believing him to be innocent, Powell decided to take Atkins back to Seacouver. Knowing his position was at risk, Crowley used his mob to attack Powell and Atkins and attempted to lynch the latter. Crowley's plan backfired, however, when Duncan, saved Powell and Atkins, and his wrath fell upon Crowley.
Their fight took place in front of Desiree's cabin and Duncan was able to defeat him. Bfore beheading him, Crowley commented that "In the future, I'll remember to leave your friends in peace." Duncan replied: "What Future?" and beheaded Crowley, and avenging Desiree.
Howard Crowley's unique choice of weapon is the Scottish claymore.