Lester W. Stiles, Deschutes County Sheriff (ret.) December 7, 1945 – January 6, 2023


Last updated 2/21/2023 at Noon

Sheriff (ret.) Lester W. Stiles passed away January 6, at his home in Caldwell, Idaho, from a series of non-COVID related lung issues. He was born December 7, 1945 in Pensacola, Florida, where his father, Marine Captain William Robert Stiles, was teaching hand-to-hand combat. June Stiles was Les’ mother.

As a child and with his sisters, Laura and Donna, the family lived in Hartford, Connecticut, Little Rock, Arkansas, Charlotte, North Carolina, Houston, Texas, Joliet, Illinois, and Naperville, Illinois.

Les attended Naperville High School, after which joined the United States Army and was stationed on the DMZ in Korea.

Commissioned an engineer Second Lieutenant at the age of 21 years, he was assigned as company commander in Fort Belvoir, Virginia.

After serving six years on active duty, he left to attend college and joined the Army Reserves with Special Forces.

Always seeking new experiences and skills, Les completed many Army schools including Airborne, Special Forces Underwater Course, and Pathfinder.

Les and his wife, Carol, were married in 1974. Upon completion of a Bachelor of Arts degree at Illinois State University, Les and Carol toured the country and ultimately settled in Colorado. Les’ original intention was to be an English teacher, but he was hired as a rookie patrolman by Northglenn, Colorado Police Department and found his true calling. While with Northglenn Police, Les taught undergraduate law enforcement college classes and attained a master’s degree in public administration at University of Northern Colorado-Greeley.

After six years with Northglenn, the family moved to Moab, Utah where Les was sworn in as police chief. Two years later they moved to Bend, and found “their” community, where they remained for 36 years.

Hiring on as a patrol officer with Bend Police Department, Les moved through the ranks attaining the position of Lieutenant. He always said the best job was being a watch commander. During the 17 years he served with Bend Police, Les taught law enforcement classes at Central Oregon Community College. He also owned a fly-fishing guide business working with Stringham Outfitters.

In 2000, Les was elected Deschutes County Sheriff and took office in January, 2001. He was a servant-leader who led with vision, compassion, and humor; always with an eye on the future and the best outcomes for the public.

Les and his team accomplished many things, including Sheriff’s Office and jail certification, Shop With a Cop, the COPY program, the largest successful big-animal criminal case in the state, installation of a cyber-crimes unit, improvement in fund accountability, and permanent funding. Deschutes County Sheriff’s office is still the only one in the state not funded through the general fund.

Always a teacher, one of his greatest joys as sheriff was attending the Adult Basic Education graduations in the jail. Elected to two terms, he retired in 2007 having achieved all the goals he set for the Sheriff’s Office.

Following his retirement, Les founded a consulting business, Legacy Leadership, working with City-County Insurance and Curry County among others. Following Legacy Leadership, Les taught master’s level leadership and ethics classes for Concordia University. In 2015, Les assumed the interim police chief position at Prineville Police Department, where he served for 18 months. He and his team attained law enforcement accreditation for that department.

Les had many interests and achievements and continually sought new challenges, both physical and mental. An avid reader, he was articulate on many topics. He attained many advanced certificates in law enforcement. He was a pilot. But at his core he was a teacher and a mentor and never missed an opportunity to support and guide someone, whether it be casting a line, teaching a niece to shoot, or guiding a young officer on officer safety.

Les’ peace came from fly-fishing and he was always ready for the next adventure.

Memberships included Oregon Association of Chiefs of Police, National Association of Chiefs of Police, Oregon Sheriff’s Association, Special Forces Association, and Co-Serve International.

Les is survived by his wife of 48 years, Carol; grandson Zach Stiles, Bend; daughters Leslie Stiles, Richmond, Virginia (grandson Mark Stiles and great-granddaughters Salem and Jordyn Stiles); Kasandra Stiles Henry, Boise, Idaho, (David Henry and granddaughters Jamie and Olivia Henry); sisters Donna Stiles, Chicago, Illinois, and Laura Stiles Bagshaw, Greenbrae, California; brothers-in-law Mike Pugsley (Rose) Tacoma, Washington, Kent Pugsley (Debbie), Colorado Springs, Colorado, Chris Ellsworth (Kelly), Bend; sister-in-law Beth Cummings, Woodbine, Iowa; and many nieces and nephews.

He is predeceased by his precious daughter Kristin Stiles, parents Bob and June Stiles, sister-in-law Kelly Pugsley Ellsworth, and beloved mother-in-law Lavonne Stenzel.

A celebration of life is scheduled for March 4, 1 p.m. in the Middle Sister Building at the Deschutes County Fair & Expo Center.

The family has established the Les Stiles Legacy Leadership Scholarship through Oregon Community Foundation, which will support college students pursuing a career in public safety. In lieu of flowers or other memorials, please feel free to make a contribution to this fund at http://oregoncf.org/stiles-scholarship-fund.


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