Lieutenant Colonel David Cummings has over 23 years of service with the JDF. He is a graduate of several prestigious military institutions around the world, including the Royal Military Academy Sandhurst (UK) where he was a multiple award winner including best overseas student, the UK Royal Military College of Science (Dean's Prize), the UK Defence Academy, the School of Infantry Warminster (UK), and the United States Command and General Staff College.

Lt Col Cummings is an Aeronautical Engineer (Cranfield, UK), and was instrumental in the acceptance and introduction into service of a complete new JDF helicopter fleet in 1998. Lt Col Cummings is a also winner of a prestigious British Government Scholarship (Chevening) in 2003, and holds two Masters Degrees in Defence Administration (UK), and in Military Arts and Science (US). His two Masters theses are entitled "Strategic Capital Sourcing Options for the Jamaica Defence Force", and "Demilitarization: Is It Worth It"

He was a member of the JDF Strategic Defence Review team (2006), and is currently the Commanding Officer for 1 Engineer Regiment (JDF). Prior to this, Lt Col Cummings served as a Staff Officer (J5) with responsibility for JDF Strategy, Plans, Policy and Transformation. He has also served at the JDF Air Wing (Second-in-Command, and the Aircraft Maintenance Officer), as well as in the Support and Services Battalion and the Second Battalion The Jamaica Regiment (2JR). Whilst in 2JR, he served in several appointments, including the Regimental Signals Officer, Intelligence Officer and Adjutant. He has also served as the Detachment Commander (Station Manager) for the JPS Rockfort Diesel Station, and has been an Instructor at the Caribbean Junior Command and Staff College.

He has held numerous other appointments throughout his career, and has attended/conducted many aviation related and strategic level conferences, courses and negotiations on behalf of the JDF, in the US, UK, Canada, France, Mexico, Germany, Brazil, Spain, and China. He was one of the principal forces behind the establishment of the Jamaica Military Aviation School, and is the recipient of the Medal of Honour for Meritorious Service to the JDF. He is currently the Chairman of the JDF Website Committee, and the JDF ICT Steering Committee.

Lt Col Cummings is a Justice of the Peace for the Parish of Kingston, and is also a Member of the Royal Aeronautical Society, Jamaica Rifle Association, and the Liguanea Club. He is a registered Professional Engineer, and enjoys playing squash, running, travelling and watching Formula 1.

He is currently separated, and has a daughter Alianne.