A native of East Hartford, Connecticut, Captain Winward received a Bachelor of Arts in Biblical Studies from Gordon College in 1983. After studying theology at Gordon-Conwell Theological Seminary, he entered Naval Officer Candidate School and was commissioned in 1986. Upon completion of Surface Warfare Officer School in 1987, he served as commissioning Navigation Officer aboard USS SAN JACINTO CG-56 and then as Main Propulsion Assistant on USS SAVANNAH AOR-4 in 1989.
After completing his obligated service in 1991, Captain Winward pursued ordination in the Episcopal Church, during which time he served as Regional Manager for In-Place Machining Company, Chesapeake, VA. In 1994, he attended Virginia Theological Seminary where he was selected as their exchange student to Ridley Hall, Cambridge University, England. Upon graduation in 1997 with a Master in Divinity, he was called as Assistant Rector to St. Andrew’s Episcopal Church in Newport News, Virginia. While there, Father Winward co-founded and was appointed co-chairman for the Episcopal Church’s Committee on Science, Technology and Faith. From 1999 to 2002, he served as Rector of Trinity Episcopal Church, a historic parish in Saco, Maine.
In 1998, Captain Winward transferred from the Individual Ready Reserves to the Naval Chaplain Corps Reserves where he was assigned to Naval Hospital Bethesda Detachment 1006 in Portland, Maine and later 1/25 Marine Battalion in Devens, Massachusetts. In response to the 911 attacks – and after serving at the National Naval Medical Center to support Pentagon recovery efforts – Chaplain Winward returned to active duty. From 2002 to 2004, he served as Squadron Chaplain for Destroyer Squadron NINE in Everett, Washington and deployed with the USS CARL VINSON CVN-70 Strike Group in support of Operation Enduring Freedom. From 2004 to 2006, Chaplain Winward was assigned to 3rd Marine Air Wing at Camp Pendleton, California, during which time he deployed to Al Anbar Province, Iraq with Marine Wing Support Squadron 372. In 2007, Chaplain Winward earned a Master of Theology in Ethics from Princeton Theological Seminary followed by completion of Air Command and Staff College (JPME I) and Joint and Combined Warfighting School (JPME II). From 2007 to 2010, he was assigned to Joint Forces Staff College, Norfolk, Virginia where he served as Command Chaplain, Ethics Chairman and JPME II Assistant Professor. From 2010 to 2013, he served as Regimental Chaplain for 5th Marines Regiment, Camp Pendleton, California with which he deployed to Helmand Province, Afghanistan. From 2013 to 2016, Chaplain Winward served as Deputy Command Chaplain for U.S. Special Operations Command and Adjunct Faculty at Joint Special Operations University, co-located in Tampa, Florida – during which time he was named the 2015 Adjunct Faculty Member of the Year. From 2016 to 2018, he was assigned to U.S. Marine Forces Special Operations Command, Camp Lejeune, North Carolina, as Force Chaplain. From 2018 to 2020, Chaplain Winward served his 0-6 milestone assignment as Force Chaplain for Commander, Naval Forces Japan and Commander, Navy Region Japan where he coordinated Navy Chapels in the Western Pacific and Indian Ocean. Having served as the Command Chaplain for U.S. Cyber Command at Fort Meade, Maryland from 2020 to 2022, he will complete his final assignment in 2024 as the Senior Chaplain for the National Security Agency and Central Security Service, also at Fort Meade.
Since 1987, Chaplain Winward has been married to the former Kathleen “KC” Collopy – with whom he has two adult sons, Christian and Matthew. Chaplain Winward’s awards include: Fleet Marine Force Officer Qualification (Chaplain), Defense Superior Service Medal, Legion of Merit, Defense Meritorious Service Medal (2), Meritorious Service Medal, Joint Commendation Medal, Navy Commendation Medal (3), and Navy Achievement Medal, as well as numerous combat and unit awards. His personal interests include long-distance bicycle touring, flying, boating, and scuba diving.