Michael K. Masterson

Mr. Michael K. Masterson, of Alexandria, Virginia, died on Tuesday, March 26, 2024, peacefully at his home following a courageous and brave five-year battle with cancer. He was 71. 

He leaves his beloved daughter and son, Emma B. Masterson Shaw (Christopher), of Boston and Thomas J. Masterson of Lowell, MA; his life partner, Karen Bruce of Alexandria, Virginia; his former wife, Kathleen (Barry) Masterson of Plymouth; his brother, William F. Masterson, Jr. (Stacia) of San Jose, California; and several nieces, nephews, and their families.

Michael was born in Worcester, Massachusetts on August 18, 1952, a son of the late William F. (World War II U.S. Army Captain) and Jean R. (Crawford) Masterson.  He moved as a child with his family to Indianapolis, Indiana and then Chicago, Illinois where he graduated from Loyola Academy, a Jesuit preparatory school in Wilmette, Illinois. Upon graduation, he was drafted into the United States Army, one of the last draftees of the Vietnam War, and served in the (then) Federal Republic of Germany as the war in Vietnam was ending. After his discharge he went ‘home’ to New England and earned his Bachelor of Arts degree from Boston College.  

From there he launched an impressive 40-plus year career as an acquisition consultant, senior subject matter expert and attorney. He worked in research think tanks in Washington, DC; supported the Department of Defense/U.S. Air Force major weapon system acquisition programs and later, helped manage a boutique veteran-owned small business providing acquisition support to Federal agencies. He practiced as an Attorney-at-Law in Massachusetts. 

He was accepted into the prestigious School of Advanced International Studies (SAIS), Johns Hopkins University, graduating with a Master of Arts degree. He later returned to his native Massachusetts and supported the U.S. Air Force Airborne Warning and Control System (AWACS) Program Management Office, Hanscom AFB, MA from 1985 to 2003.

Continuing his academic journey, in 1993 he received his Juris Doctor degree from Suffolk University in Boston and became a practicing attorney in Waltham and Lexington, Massachusetts while continuing his senior consulting roles at Hanscom AFB in Bedford, MA. As a patriot, Michael deployed from his then home in Lexington, Massachusetts in 2003 as a civilian serving in-country in Iraq during the war supporting U.S. objectives and the Coalition Provisional Authority (CPA) and, later, the Multi-National Force – Iraq (MNF-I). While there he managed humanitarian and reconstruction efforts in Mosul, Iraq on behalf of the Department of State, U.S. Regional Embassy Office-Mosul and the U.S. military. Later, he was handpicked to serve as the Chief of Party supporting the U.S. State Department Rule of Law project in Iraq, integrating the police-courts-prison system. He also went on to play key roles in rule of law and justice projects in Egypt and South Sudan. He was a genuine patriot serving our country’s mission objectives wherever he could contribute.

He was a Commonwealth of Massachusetts, Supreme Judicial Court, licensed attorney, and a member of the Massachusetts Bar Association. 

He was a voracious reader who was very steeped in military history with a lifelong love of all things about Julius Caesar and Roman History. 

More importantly about Michael, he deeply loved his family and was a true and generous friend to many across the years. His greatest blessings in life were Emma and Thomas. People who met him even briefly were impressed with his wit, charm, knowledge, and uncanny ability to listen and learn about each person. He proudly served his country and was a patriot through and through. 

While we are heartbroken at losing Michael too early, his family and friends will joyfully and proudly honor and remember Michael’s life by gathering for calling hours in The Joyce Funeral Home, 245 Main Street (Rte. 20), Waltham, Massachusetts on Tuesday, April 2nd from 4 to 7 p.m. and again at 9:00 a.m. on Wednesday morning before leaving in procession to Saint Mary’s Church, 133 School Street, Waltham where his Funeral Mass will be celebrated at 10:00 a.m. Burial will be in Massachusetts National Cemetery, Bourne, Massachusetts on Thursday, April 4th at 10:45 a.m. 

In lieu of flowers please consider a donation in his memory to some of Michael’s favorite charities; the Gary Sinise Foundation, Tunnel to Towers, or St. Jude Children’s Research Hospital.