A Tribute to Tom Grasso (1973-2026) Heroic Soldier, Teacher and Coach

By Phil Devlin

(May 12, 2026) — On June 10, 2016, Higganum’s Tom Grasso, a 1991 HKHS grad, former Haddam-Killingworth Middle School teacher, and former assistant varsity football coach at Haddam-Killingworth High School, was awarded our nation’s third highest military medal for valor in combat—the Silver Star. We celebrated Tom’s heroic and selfless actions then; now we must mourn his tragic death in North Carolina this month at age 52.

Ten years ago I wrote about Tom’s heroism for this publication. Here is an excerpt: “Sergeant First Class Grasso has served overseas on multiple combat deployments in both Iraq and Afghanistan over the past several years. Most recently, he served in Afghanistan from August 2015 to February 2016. During this last deployment, Tom was cited for his selfless and courageous actions in combat for action between September 29, 2015 and October 4, 2015… SFC Grasso volunteered to travel in an unarmored, two-person 4×4 ATV… During the assault to liberate the Taliban-seized Afghan city of Kunduz, his element endured multiple near-ambushes and IED strikes by enemy forces. SFC Grasso manned an M240 machine gun mounted on his ATV; he was cited for saving many lives with his ‘withering fire’ under heavy and sustained enemy fire. On one occasion, he ‘deliberately’ exposed himself to heavy enemy fire by placing his unarmored ATV between the enemy and his fellow soldiers who were trapped in an intersection. SFC Grasso placed accurate and effective fire on the enemy position, thus saving multiple American lives. Upon finally reaching their objective, SFC Grasso left his vehicle to occupy a tower from which he used both precision sniper fire and hand grenades to protect the lives of his men and Afghan partners for the next four days during wave after wave of relentless and sustained enemy assaults.”

(Photo above: Tom Grasso, right, with his brother Rob, a 1987 HKHS graduate and former HKHS Special Education Aide)

Put another way, along with 23 other Green Berets, Tom was in constant combat for 130 straight hours, fending off repeated attacks by an estimated 2,000 members of the Taliban. One of the other Green Berets there was Captain Pat Harrigan. Now a Congressman from North Carolina’s 10th District, on April 29, 2026, Congressman Harrigan made a compelling case that Tom Grasso’s Silver Star award should be upgraded to the Congressional Medal of Honor. Harrigan concluded his five-minute remarks with these words: “I know every word of that citation to be true, because I was one of the teammates he rescued.” (Harrigan’s full and moving testimony on Tom can be found on YouTube. His upgrade proposal will be reviewed shortly.)

Tom’s former teacher, colleague and friend Charlie Macunas had this to say about Tom: “I had the honor and privilege of interacting with Tom on numerous levels; first, as a student in my eighth grade American History class. I often incorporated music into many of my lessons. For a chapter on Vietnam, I played a recording and distributed the lyrics to ‘Ballad of the Green Berets’ by Staff Sergeant Barry Sadler. Little did I know that fourteen-year-old Tom would go on to become a heroic and highly-decorated member of the Green Berets. I last saw Tom when he returned to HKHS along with his son, Bode, where I proudly inducted Tom into the HK Wall of Fame.”

(Photo above from Wall of Fame induction: Left to Right, Charlie Macunas, Tom Grasso, and Phil Devlin)

Long time HKHS teacher and football coach Dennis O’Rourke had this to say about Tom: “Tom Grasso was an exemplary athlete and football player. He was a team leader whose skills and unswerving commitment to goals made him a standout athlete. As a coach, Tom clearly helped instill in our young players the values that he lived by: commitment, dedication, and a desire to win. Tom provided a positive, energetic role model for our football team. He demonstrated an outstanding work ethic, a burning desire to excel and a love of team. His membership in our program both as a player and coach will provide a legacy of excellence and dedication to a common goal.”

Tom’s former HK Middle School principal and colleague Mim Wagner had this remembrance about Tom: “As middle school principal, I had the distinct privilege of working with Tom Grasso from my first year in 1998 until he requested a leave of absence for military service in 2001. Tommy Grasso was an extraordinary asset to our middle school community. A hometown student and highly regarded athlete, he was, more importantly, an exceptional educator. He believed deeply in the value of hard work, exemplified that commitment in his daily practice, and upheld high standards for student conduct. Tom expected each of his students to perform to the best of their abilities, and he devoted himself to helping every one of them succeed   His students worked hard because they wanted to earn his respect. He loved history class most of all. Tom could be serious and he could be fun and was masterful about the timing of each. It is difficult to fully convey the depth of admiration our students, their families, and our staff held for Tom until one recalls the grief on their faces when he informed them that he would be leaving for boot camp. I always remained hopeful that he might one day return to our classrooms, but our nation had a greater need for the talents and character of this remarkable young teacher.”

(Photo above: Tom Grasso—top right—with his Middle School teaching team.)

Tom leaves behind his wife, Denna, and his three children: daughters Aynslee and Cayden and his son, Bode, (photo above) as well as his parents, John and Denise Grasso, and his brother, Rob, and Rob’s wife, Michele; also, his nephew, Jonathan, and Jonathan’s wife, Amber, and his niece, Ashley.  A service for Tom will be held at Wake Forest on May 30, 2026. Burial with full military honors will be held later at Arlington National Cemetery. Further details for funeral arrangements and burial will be updated soon on this site. On a personal level, I have lost a former excellent teaching colleague and a good personal friend. May our memories of his dedication to all that he did and his outstanding bravery sustain us in this difficult time.

Photos provided by Phil Devlin