Chief Warrant Officer Dempsey was born on the 4th of April, 1961 in Larne, County Antrim in Northern Ireland, and his family later immigrated to Canada in 1973 to reside in White Rock, British Columbia. He enrolled in the Primary Reserve, 15 Field Regiment RCA, in April 1983 at Bessbourough Armouries in Vancouver, British Columbia. As a young private he was able to train not only with the Reserves but along side Regular Force members. From 1983 until 1985 he was employed as a gunner in 31 Battery until he sought a full time career with the Regular Force. In June, 1985 he was sworn in as a Regular Force Artilleryman and sent to Canadian Force Recruit School Cornwallis. After completing his basic training he was then posted to the RCA Battle School in Shilo, Manitoba where he graduated as a 021 Gunner.
On completion of his trades training, he was posted to Canadian Forces Base Gagetown, New Brunswick where he was employed as a gunner in Whiskey Battery. During his time spent with the school of excellence, he held such positions as Detachment 2IC, Detachment Commander, and Instructor. In 1990, it was time for him to spread out and experience more training opportunities, so he was posted to 1 Royal Canadian Horse Artillery located at Canadian Forces Base Europe. As a sergeant in Zulu Battery, he was employed as the Detachment Commander of an M109 Howitzer. He was able to participate in several fall exercises conducted in Graf, Munster and several small towns within the country side of Germany. Due to the base closure in Lahr Germany his stay was cut short and was then posted to a new assignment in Canada.
In November 1991 he was posted to 15 Field Regiment as part of the 10/90 pilot program, where he employed his experience to the Reserves in such areas as: Gunnery, Recce, and Command Post duties. He remained in 15 Field until 1995 when he was posted to Canadian Forces Base Petawawa, Ontario as a Detachment Commander in Fox Battery, 2 RCHA. During the time that he served in Petawawa, he was employed as a Gunnery Instructor for the Reserves, a Detachment Commander, and Instructor at the RCR Battle School teaching basic officer and leadership courses. He had an opportunity to deploy overseas during his time in 2 RCHA completing two six month tours of duty in Bosnia. He was an avid member of the 2 CMBG Pipes and Drums, in which he was able to participate as a drummer in many change of command parades, mess dinners, town parades and even compete in several pipe and drum competitions at the highland games in Ontario.
Upon completion of his second tour in 2000, he was posted to Canadian Forces Base Shilo, Manitoba, back to the first and the finest, 1 RCHA, as a Warrant Officer in “C” Battery, holding positions such as: Battery Quarter Master, and later Troop Sergeant Major. He was able to assist in training “C” Battery personnel who where to deploy on OP APOLLO Afghanistan. He was also appointed the Administrative Officer for the 1 RCHA Pipes and Drums, where he was again employed as a drummer. During his short stay in Shilo, he was given the opportunity to be posted to his native province British Columbia in 2001, where he accepted the challenge as the new Regular Support Staff for 15 Field Regiment. He remained in the position until 2005, when he retired from the Regular Force and transferred directly to the Reserve Force. He was promoted to MWO in 2005 and assumed the position as Battery Sergeant Major for 31 Battery, 15 Field Regiment until Feb 2013. Chief Warrant Officer Dempsey completed his qualification for Chief Warrant Officer in 2012 and was promoted Chief Warrant Officer on 20 Feb 2013 and was appointed the Regimental Sergeant Major of 15 Field Regiment.
Upon retirement from the Regular Force he has taken on new challenges in the civilian world where he started a career in the gaming industry as a security supervisor and later became involved in the Armoured Car world where he still continues his civilian employment as of today. His hobbies include kayaking and shooting.