Major Karl “K.C.” W. Cutler

Major Karl “K.C.” W. Cutler, 36, raised in Mattituck, passed away on Oct. 26, 2025, at Straub Benioff Medical Center in Honolulu, Hawaii, after open-heart surgery necessitated by endocarditis.

K.C. loved being a Tucker, graduating with the Class of 2007. He played trumpet in the school band and was Mattituck’s varsity goalkeeper during his sophomore, junior, and senior years. He also played on travel teams, participated in the Long Island Junior Olympic Soccer League, and was selected at 15 to be the goalkeeper for the Long Island team at the Empire State Games. He participated in the NJROTC program, competing with the Trick Rifle Club and athletic teams. He was proud to be part of the school’s first revived lacrosse team and served as its captain in 2007.

He enjoyed riding dirt bikes, taking his Chris-Craft boat out with friends, and working summers at Splish Splash, where he advanced from lifeguard to supervisor.

K.C. attended the Virginia Military Institute, where he thrived in the disciplined environment and served as First Platoon Lieutenant for Hotel Company. He graduated in 2011 and, after completing Officer Candidate School in 2013, was commissioned as a Field Artillery Officer. He completed the Basic Officer Leader Course at Fort Sill, Oklahoma.

He began his military career with the 1st Infantry Division, 1st Battalion, 7th Field Artillery Regiment at Fort Riley, Kansas, serving as Headquarters Battalion Fire Support Officer, Platoon Leader, and Executive Officer. He deployed to Kuwait in 2014 and to Poland and Germany in 2017 in support of Operation Atlantic Resolve.

After graduating from the Field Artillery Captains Career Course, he was assigned to the 25th Infantry Division Artillery Brigade in Oahu. During his six years there, he served as the 3rd Battalion, 7th Field Artillery Regiment’s Fire Support Officer, Battalion Fire Direction Officer, Charlie Battery Commander, and Brigade Headquarters and Headquarters Battery Commander. Following command, he served as a Ground Liaison Officer in the 5th Battlefield Coordination Detachment. During these assignments, he earned an MBA from Syracuse University’s Whitman School of Business in May 2024. In 2025, after his promotion and graduation from the Command and General Staff College—where he completed his second master’s degree—he was reassigned to the 25th Infantry Division as Joint Air Ground Coordination Center Chief and Division Fire Support Coordinator.

In 2020, K.C.’s life changed forever when he met his future wife, Jackie Milazzo. Though they had grown up only a half-hour apart, they often joked that it took traveling 5,000 miles to find each other. They fell in love and with Oahu. They enjoyed exploring the island, driving in K.C.’s Ram truck, discovering new places to eat, and grilling meals on his Traeger. They married on May 17, 2024, in a beautiful Hawaiian setting. After a year in Kansas for K.C.’s schooling, they were delighted to return to Oahu, where they purchased a townhouse in Ewa Beach and settled into a happy life with their much-loved cat, Buddy.

A full Military Memorial Ceremony was held on Oct. 31, 2025, at the Main Post Chapel on Schofield
Barracks. The chapel was filled with officers and enlisted soldiers whom he had led. The ceremony included the Roll Call, Firing of Volleys, and Taps. Lieutenant Colonel Charles A. Staub said, “His legacy of leadership and integrity is woven into the fabric of this unit… his no-nonsense approach, paired with sharp wit and steady demeanor, made him not only effective but deeply respected and
beloved.”

For those of us who loved K.C., we will remember his loyalty, his kindness, and the joy he brought into
our lives. He was his father’s shadow and his parents’ greatest delight. K.C. was never happier than when Jackie became part of his life, and he was grateful for every moment with her. Only death could part him from her.

In the spring of 2026, a Memorial Mass and reception will be held at St. Mark’s Episcopal Church in
Westhampton Beach, where K.C. served as an acolyte. Notification will appear in the local paper and
around Mattituck.

He is survived by his devoted wife, Jackie Cutler; and his mother, Mary Fitzpatrick-Cutler; and is preceded in death by his late father, Karl Thomas Cutler. He is also missed by his in-laws, Mr. and Mrs. James Milazzo; his godmother, Patricia Pfeifer; and his aunt, Pamela Cutler.

For those who would like to donate in Major Karl W. Cutler’s memory, VMI Class of 2011: Online — gifts may be designated in his honor.