Jonathan’s family has been in the United States since before America's founding. Jonathan’s grandpa on his mother’s side was a farmer in Clay County, Kentucky before he died at the age of 101. Jonathan’s grandpa on his dad’s side was a coal miner in West Virginia and died from cancer related to black lung disease. Jonathan is the son of John M. Holliday (deceased) and Oda M. Holliday. John Holliday was a former Air Force Officer and Air Force Civil Servant. John Holliday is buried at Camp Nelson National Cemetery in Jessamine County, Kentucky. Oda was a Hospice Nurse before retiring. John and Oda met at Berea College. Jonathan has an identical twin brother and two sisters. Jonathan’s brother is a retired Lexington Police Officer.

Jonathan is Married and has three children, Justin (14), Joshua (12), and Katherine (9).  His family includes two dogs, an Australian Shephard named Ori and a Malinois X named Hannibal.  His family also includes two cats, Gizmo and Mittens. 

Jonathan’s wife, Jessica has an undergraduate degree in Community Health Education and a graduate degree in Public Health from Eastern Kentucky University.  She served in public health positions at Eastern State Hospital, the Lexington Public Health Department, and the Kentucky Department for Public Health - Cabinet for Health and Family Services.  She is currently not employed in the public or private sector, focusing instead on home schooling their three children.  

Jonathan and Jessica were both raised in the United Methodist Church but are currently Baptists. They are lifelong registered Republicans.  They have been residents of Mercer County since buying a farm there in 2011. 

Jonathan M. Holliday began his 24-year military career, starting on active duty as a Private First Class in the Infantry.  During his four years of active enlisted service, he attended US Army Infantry Basic One Station Unit Training (OSUT), US Army Airborne School, and US Army Sniper School.  His first assigned unit was the First Cavalry Division at Fort Hood, Texas.  He served in various positions in the First Battalion, Ninth Cavalry Regiment of the First Cavalry Division, including as a Bradley Infantry Fighting Vehicle Driver, Dismounted Rifleman, Machine Gunner, Javelin Missile System Gunner, Infantry Fire Team Leader and Sniper Team Leader.  He earned the Expert Infantrymen’s Badge, the Combat Infantryman’s Badge, and the Order of the Gold Spur.  He deployed to Iraq as a Sniper Team Leader and his decorations during his enlisted service include the Purple Heart, two Army Commendation Medals, The Iraq Campaign Medal, Global War on Terror Expeditionary Medal, Global War on Terror Service Medal, the Good Conduct Medal, and various other awards. 

Lieutenant Colonel Holliday left active duty and attended Officer Candidate School with the Kentucky Army National Guard, commissioning in 2006 as a second lieutenant.  He branched Military Police, and during his service as a Lieutenant he served as a Platoon Leader and deployed in 2008 to Baghdad, Iraq and served as a security Platoon Leader and Police Transition Team Chief on a Military Police Brigade staff.

Following his time as a platoon leader Lieutenant Colonel Holliday was the Executive Officer of the 223rd MP Company, and eventually took command of the 1103rd Military Police Detachment (Law and Order), originally stationed in Harrodsburg, KY.  Lieutenant Colonel Holliday commanded this 45 Soldier Military Police Law and Order Detachment for four years and conducted numerous Kentucky National Guard state active-duty missions including the Kentucky Derby.  His unit was certified to conduct law enforcement operations on Fort Knox, KY.  His unit deployed to Afghanistan and conducted operations across three bases and two regional commands.  His unit conducted law enforcement patrols, traffic collision investigations, criminal investigations, customs and border enforcement, force protection, undercover operations, drug suppression, and was the armored Quick Reaction Force for a NATO Base.  His unit also provided the personal security detail to the deputy commander of Regional Command- North.

Following his time in command of a Law Enforcement Detachment he served in various active and reserve positions including Area Security/Force Protection Officer and Section Chief of a Maneuver Enhancement Brigade, Executive Officer of a Military Police Battalion, as a project and disaster planner, Deputy Chief of Security Cooperation and Bilateral Affairs Officer at a US Embassy in Africa, a Training Officer at a Corps level at the United States First Army, and most recently as the Chief of the Antiterrorism Branch at US Army Central. 

Lieutenant Colonel Holliday completed Military Police Officer Basic Branch Course, Military Police Captain’s Career Course, US Army Command and General Staff College, the US Army Conventional Physical Security Course, Security Cooperation Management – Overseas Course, US State Department Foreign Affairs Counterterrorism Training Course, the Department of Homeland Security Customs Border Clearing Agent Course, Defense Threat Reduction Agency (DTRA) Mission Assurance Assessors Course, First Army Observer Coach/Trainer (OC/T) course, and he is US Army Combatives Level I and II qualified. 

Lieutenant Colonel Holliday’s decorations during his service as an officer include two Bronze Star Medals, three Meritorious Service Medals, two additional Army Commendations, Iraq Campaign Medal, Afghanistan Campaign Medal, NATO medal, the Order of the Marechausee, the Master Combat Infantrymen’s Badge, and numerous other decorations.  Lieutenant Colonel Holliday is currently a Lieutenant Colonel in the Kentucky National Guard.  He holds a top-secret security clearance with eligibility for secret compartmented information (TS/SCI).   

Jonathan began his civilian law enforcement career with the Lexington Police Department in 2009 following his deployment to Iraq.  Constable Holliday graduated from the 8-month long Lexington Police Academy as the Academic Award Winner for his class.  Jonathan worked throughout various sectors and shifts in Lexington/Fayette County during his tenure, policing urban, suburban, and rural areas of the Lexington-Fayette Urban County.  Jonathan is bike patrol certified, patrol rifle certified, taser certified, and attended the Lexington Police Field Training Officer Academy.  Prior to leaving the Lexington Police Department, he successfully passed promotion testing, and he was placed on the promotion list for Sergeant.

Constable Holliday was elected as the Mercer County Constable of the Third District in 2022, taking office in January 2023.  Constable Holliday is one of a small fraction of Constables to maintain an active Kentucky Law Enforcement Council Peace Officer Professional Standards Certification as required in legislation passed in 2022 for newly elected Constables to be considered law enforcement officers.  Since being elected, Constable Holliday has completed the Department of Criminal Justice Training (DOCJT) Basic Officer Skills course, DOCJT Constitutional Law and Penal Code Update, the National Tactical Officer Association Basic Special Weapons and Tactics Course (SWAT), The DOCJT Basic Investigator Course, Armament Systems and Procedures (ASP) instructor course, and American K9 Interdiction (AK9I) certified patrol/detector dog trainer course with his Police K9, Hannibal.

Constable Holliday holds an associate degree in Law Enforcement from Midway College, an undergraduate degree in Assets Protection and Security from Eastern Kentucky University, a Graduate Degree from Webster University in Business and Organizational Security Management, and a Master’s in Military Arts and Sciences – Strategic Studies from the US Army Command and General Staff College (CGSC).  Constable Holliday holds the US Army Additional Skill Identifier in Strategic Studies, a graduate certificate in Interagency Studies from CGSC, and was published in a peer reviewed military journal as a West Africa Scholar at CGSC.