Executive Board

Sheriff Gary Simpson

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Gary Simpson was hired as a Deputy Sheriff in 1984. As he promoted through the ranks, Sheriff Simpson worked in several areas of the Sheriff's Office to include  Patrol,  Marine Unit, and K9 unit.  He was promoted to the Rank of Corporal in ’93, Sergeant in ’96, and appointed to Chief Civil Deputy in ’98.


Gary was elected as Sheriff effective January 2015, re-elected in 2018.  He is ta graduate of the 108th Session of the National Sheriff’s Institute and the 206th Session of the FBI National Academy.


Sheriff Simpson is actively involved in the community, where he serves on several boards to include:

  • Compassionate Friends of Kitsap County Advisory Board
  • Peninsula Work Release Advisory Board 
  • Kitsap 911 Policy Board 
  • State Insurance Commissioner’s Insurance Fraud Advisory Board
  • Mentor with Bremerton School District's AVID Program

Jeff Rogers

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Jeff Rogers started his law enforcement career in 2001, with the Edmonds Police Department.  In 2004, Jeff and his family moved to Goodyear, AZ where he continued to serve as a police officer with the Goodyear Police Department.  


During his career with Goodyear PD, Jeff rose through the ranks from Officer to Deputy Chief of the Enforcement Bureau (Patrol and Criminal Investigations Division).  Jeff served in various divisions and assignments including Patrol, Traffic, Professional Standards, Criminal Investigations, and Support Services.  


Jeff served as the President for the Goodyear Police Officers Association and also helped found the Goodyear Police Officers Charitable Foundation to help bridge the gap between community and police.  Jeff holds a bachelor's degree in Criminal Justice from the Arizona State University and is also a graduate of the 130th Administrative Officers Course at the Southern Police Institute ("SPI").  He is also a graduate of the IACP's Leadership in Police Organizations.

Penny Sapp

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Penny Sapp was hired as a Corrections Officer with the Kitsap County Jail in 2002.  Penny rose through the ranks and she currently assigned as a Support Lieutenant.  Over the course of her career in corrections, she has served in all areas of the jail including jail alternatives and training. 


Penny is currently completing her dissertation to receive a PhD in Philosophy of Public Policy Administration.  Penny is actively involved in the community and serves on several local boards, which include: 

  • Kitsap Shop with a Cop 
  • Kitsap County Fair and Stampede Advisory Board 
  • Kitsap Sexual Assault Center 

Maaren Stroble

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Maaren Stroble was born and raised in Kitsap County and is the passionate about serving her community in many capacities.  Maaren holds an AA degree in Retail Management from Bassist College in Portland, OR.

Maaren is a majority member of the Washington & Idaho International Order of Rainbow for Girls where she has helped raise thousands of dollars for service projects.  In 2011, Maaren was appointed by the Kitsap County Commissioners to the Kitsap County Fair & Stampede board as the Commercial Exhibits Director.  Maaren began working for the Kitsap County Sheriff's Office in 1995 as the Administrative Assistant to the Patrol Division.

Jeff Taylor

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  Jeff Taylor has served the Kitsap County Sheriff's Office since February of 1988.  During his career, Jeff has served in all aspects of the corrections division. He is also serving as an executive board member with the Washington State Jail Association representing jails throughout the state of Washington as well as the Kitsap Corrections Officers Guild.

Kenneth Watkins

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Ken Watkins has been with the Kitsap County Sheriff’s Office since 1997, he is currently a Sergeant in the Correction’s Division. When Ken was an officer he fulfilled the role of the corrections officers guild president and now manages the Sergeants guild as president. Ken’s passion lies in giving back to his community in a variety of ways. Ken has coached youth sports, served as a member of the juvenile community diversion panel and was also elected and served as a school board director with Bremerton School district. Ken is certain that community outreach is a critical part of strengthening the partnership between the Kitsap County Sheriff’s Office and our diverse community. 

Citizen Representative 1

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TBD...Representative from District 1

Citizen Representative 2

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TBD... Representative from District 2

Citizen Representative 3

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 TBD...Representative from District 3