‘Loyal’ Steindler leaves Sheriff’s Office, but don’t call him ‘retired’
After nearly two decades, well-known Pitkin County deputy ready to be “doing some good for somebody” in another role
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).”
But since he turned in his uniform, badge and gun last week — Steindler doesn’t like the word “retirement” — things have changed.
“That’s one emotion I have not been feeling,” he said with a grin. “It’s amazing. I’m much less stressed.”
Still, that doesn’t mean the 64-year-old won’t miss his former job.
“I loved it,” Steindler said. “I was being paid to be part of a special group of people … to mitigate problems throughout the county. That gave me great pleasure.”
Steindler’s path to a career in law enforcement, however, wasn’t exactly preordained.
He was born in New York City but moved to his mother’s native Italy when he was just two or three months old. He spent his formative years with his parents in Europe and went to his first boarding school on the continent when he was 9-years-old.
After a few years of boarding schools in England and Switzerland, he returned to the United States, where his father enrolled him in his alma mater, Choate Rosemary Hall, a boarding school in Connecticut. But after years of enduring European-style corporal punishment for rule-breakers like himself, Steindler said he found the American system, where beatings weren’t allowed, “like summer camp.”
“When I realized I wouldn’t get beaten if I broke the rules, that was a game-changer for me,” Steindler said. “I said, ‘If you don’t hit me, I won’t do it.’ I completely went off the deep end.”
So, by the end of his freshman year — his first in the U.S. — he was promptly expelled from Choate. Though he was eventually allowed back because his father was an alum and because his years in Europe had molded him into a good soccer player, it didn’t last.
The next year — when he was 15 — he ran away from the school with a friend who was a year older and hitchhiked across the country to Aspen.
“My friend had been to Aspen to ski and he said it was the best skiing in the world,” Steindler said. “That’s why we came here. I had heard about Colorado, and I wanted to ski and be a cowboy.
“I was 15 and that’s what I did.”
Life on the lam didn’t last long though. Steindler was in a car accident and the police identified him as a runaway and notified his parents. His father wanted him to come back to school in Connecticut, but instead he applied for and received a scholarship to the Rocky Mountain School in Carbondale, and his father grudgingly allowed him to stay.
Steindler camped out and lived in a lean-to up Avalanche Creek during those years as an RMS student and, at one point, forged his birth certificate and tried to enlist in the Army at 16, which was thwarted by an uncle who lived in Denver.
“The MPs got involved because it was lying to the federal government,” Steindler said. “I was such a scrapper. I was always getting into fights.”
He graduated from RMS, however, then later got married, bought a ranch in British Columbia, Canada, for a few years, then drifted back to the Roaring Fork Valley, now with two daughters and twin sons in tow.
At that point, in 1990, George Stranahan hired him to run his cattle operation at the Flying Dog Ranch in Woody Creek. Steindler’s mother was from a farm in Northern Italy, his father had a penchant for farming and Steindler found he, too, enjoyed horses and cattle and the country life.
He worked for the venerable Stranahan — who died in May at the age of 89 — until 1999, when Stranahan decided to shut down his cattle operation.
“(Former Pitkin County Sheriff) Bob Braudis had courted me for a number of years (to be a deputy),” Steindler said. “So I called up Bob and said, ‘What do I do?’ and he said, ‘Go to the academy.’”
And so began his career in law enforcement.
Pitkin County Sheriff Joe DiSalvo said Braudis and the Woody Creek community were familiar with Steindler from his work at Stranahan’s ranch and knew he was a hard-working, loyal person.
“Bob pursued him very hard to work for us for many years,” said DiSalvo, who’s been with the Sheriff’s Office for more than 30 years. “Finally, after years of pursuing him, he gave in. I think it’s one of the best moves we ever made.”
Eighteen years later, Steindler decided he’d retire in July when he turned 65. But he had significant vacation days coming to him, so he asked to take off large chunks of time during his last year, he said. While the Sheriff’s Office doesn’t like to let employees off for long periods, DiSalvo agreed to the request and Steindler took a month off to help his aging mother.
That gave him time to think, and he came to conclusion that taking long vacations while still employed with Pitkin County wasn’t fair to his colleagues, who would have to make up for his absences.
“I didn’t want to be seen as a guy who was milking it,” Steindler said. “I’ve never done that. It’s always better to leave before you overstay your welcome.”
Pitkin County Undersheriff Alex Burchetta said he’s going to miss Steindler “tremendously.”
“I think he’s a fantastic individual,” he said. “He embodies everything the former sheriff and the current sheriff want in a peace officer.”
Burchetta has worked with Steindler the entire 14 years Burchetta has been with the Sheriff’s Office, and said he has found Steindler’s wise counsel invaluable over the years.
“He approaches things like a father,” he said. “He was always a voice of reason, a mentor, someone I could always to with questions or if I needed advice. I look forward to calling him every week for his counsel.”
DiSalvo echoed those sentiments.
“He was incredibly loyal to the Sheriff’s Office and to the people of Pitkin County,” he said. “If somebody needed help, Jesse stood up and said, ‘Put me in,’ and he did that up until his last day.
“I really, really love and admire him.”
Steindler said he’s not exactly sure what comes next and plans to enjoy time with his wife, Jill, his four children and his stepson, though he’s not yet finished working for a living.
“I’m not a rich man,” Steindler said. “I see myself as a 64-year-old unemployed man. When I know I’m doing some good for somebody, and if I can combine that with making a little money, I’m gonna be happy.”
So, in case the message is unclear, Jesse Steindler is not “retired.”
“I’ve banned the word ‘retirement’ around here,” he said. “I’ve resigned from the Sheriff’s Office.”
Across the Roaring Fork School District, three schools achieved higher ratings from 2019 to 2022, two schools had lower ratings during that time period and most remained the same.