On a warm, humid morning at Fort Magsaysay, the dim glimmer of headlamps and the rhythmic pounding of boots on pavement signaled the start of the Gimlet Challenge. Over 200 service members—comprised of both United States and Philippine Army Soldiers—gathered for this time-honored event, which rigorously tests physical and mental readiness. This iteration held particular significance, marking the first time the challenge was conducted in the Philippines and involving partners from the 102nd Infantry Battalion, 501st Brigade. Set in terrain where U.S. and Philippine forces prepare for future crisis or contingency side by side, the event underscored the importance of the unit’s war-fighting readiness, partnership, and strengthening the profession.
The Gimlet Challenge draws its name and inspiration from the "Gimlet Stick," an item officially recognized by the United States Army Institute of Heraldry and one that the Gimlets have proudly worn since 1921. Originally, a gimlet is a tool used to bore holes into rock for explosives, vital to creating roads and railways through difficult terrain. It symbolizes the resilience, determination, and adaptability of the 21st Infantry Regiment, whose motto, “Bore Brother Bore!” encapsulates the spirit of boring through the competition. Soldiers who complete the challenge earn the right to wear the Gimlet Stick on their left hip, a visible emblem of their achievement and commitment. Each challenge also includes specially dedicated identification tags named in honor of a fallen hero so that Gimlet Soldiers literally carry their memories with them.
Held on May 10, 2025, the Diamond Gimlet Challenge featured six demanding stations designed to evaluate team cohesion and endurance. Most participants—over half—were first-timers, each motivated to earn the coveted "Gimlet Stick." Teams were composed of roughly 20 U.S. Soldiers and 10 Philippine Army Soldiers, distributed among six teams. The average completion time was one hour and 45 minutes.
The challenge was conceptualized by Lieutenant Chris Cocoris and Captain Brad Torpey of 1st Infantry Battalion, 21st Infantry Regiment, Delta “Dragon” Company
supported by a capable and dedicated operations team. Each station honored a fallen hero, connecting today’s Soldiers with the values of courage, sacrifice, and discipline that define the legacy of the 21st Infantry Regiment.
Station 1 honored Staff Sergeant Brian D. Bucher, who, during a 2006 ambush in Iraq, heroically safeguarded his unit's water supply under fire. Participants re-enacted his efforts by transporting heavy water cans across a physical course.
Station 2 was dedicated to Staff Sergeant Robert Miltenberger, who saved a wounded comrade during combat in Mosul in 2004. Soldiers were pushed through a physically taxing workout to emulate his strength and tenacity.
Station 3 paid tribute to Sergeant William H. Caver, who manned a machine gun during a 1944 ambush in Ilocos. Teams completed laps and assembled an M240B machine gun, simulating the coordination and precision needed under fire.
Station 4 remembered First Lieutenant Charles R. Gates, whose leadership in stealth operations in northern Luzon required mastery of Individual Movement Techniques. Participants crawled 100 meters in buddy teams, mirroring his tactical movements.
Station 5 honored the memory of 630 Gimlet soldiers lost at Breakneck Ridge, Leyte, in 1944. Teams were challenged with casualty evacuation and medical evacuation procedures, replicating the arduous realities of jungle warfare.
Station 6 concluded the course with a knowledge-based challenge focused on the history of the Gimlet Regiment, reinforcing the legacy and traditions of the unit.
The challenge began precisely at 0200 hours. As each team crossed the finish line, fatigued and bearing the marks of their effort, participants gained not only a deeper sense of mission but also a stronger connection to the sacrifices of those who came before them. The final team completed the course by 0630, at which point the winning team—1st Platoon, Charlie Company, was announced. Their reward includes the honor of planning the next Gimlet Challenge, which will be held at Schofield Barracks in Hawaii.
This event was dedicated to Private First-Class James H. Diamond, a Medal of Honor recipient who served with Company D, 21st Infantry Regiment, 24th Infantry Division. On May 14, 1945, in Mintal, Mindanao, Philippines, he was killed while evacuating wounded comrades under heavy fire. For his valor, he was posthumously awarded the Medal of Honor on March 6, 1946. Honoring his legacy during a deployment in the very region where he served, helps join past and present, grounding today’s Soldiers in the enduring history of the unit.
Though this Gimlet Challenge was a single event during the current training exercise in the Philippines, it forged bonds of trust, mutual respect, and shared sacrifice among U.S. and Philippine Army. Taking place on the historic grounds of Fort Magsaysay, it reaffirmed the commitment to an important U.S. ally in the most consequential theater and reinforced the importance of warfighting readiness. This event also served as a reminder that today’s Soldiers stand on the shoulders of those who gave everything in service to their country. Duty!
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