Jesse Steindler at home in Woody Creek on Friday, July 16, 2021, first came to Aspen after running away from home at 15 and hitchhiking across the country because wanted to ‘ski and be a cowboy.’ (Kelsey Brunner/The Aspen Times) During nearly two decades as a deputy, then a sergeant and finally a captain with the Pitkin County Sheriff’s Office, Jesse Steindler was consistently hounded by one particular emotion. “For the past 18 years, I’ve woke up or gone to bed worried,” Steindler said last week during an interview at his home in Woody Creek. “I worried about deputies getting hurt or how things went the night before or how things will go (that day).”