Jack Cleveland Montgomery

The Cherokee Warrior Who Faced Three Enemy Positions Alone

What drives a soldier to crawl toward enemy machine guns when survival seems almost impossible? For First Lieutenant Jack Cleveland Montgomery, the answer was simple: his men were in danger, and someone had to act. On 22 February 1944, during the brutal Battle of Anzio in Italy, this Cherokee officer launched a remarkable solo attack against three German positions. His extraordinary courage would earn him the Medal of Honor and secure his place among America's most celebrated World War II heroes.

Born on 23 July 1917 in Long, Oklahoma, Jack Cleveland Montgomery was a member of the Cherokee Nation. He attended Chilocco Indian Agricultural School, studied at Bacone College, and later graduated from the University of Redlands. A talented athlete, Montgomery joined the Oklahoma National Guard before World War II. Following the attack on Pearl Harbor, he returned to military service with the 180th Infantry Regiment, 45th Infantry Division, known as the Thunderbirds.

Montgomery first experienced combat during the Allied invasion of Sicily in July 1943. His leadership soon distinguished him during the difficult fighting in Italy. He earned two Silver Stars for gallantry in action. One documented engagement occurred near Benevento on 9 October 1943, when he led his platoon against a much larger German force supported by machine guns, mortars, and armour. His men surprised the enemy, inflicted heavy casualties, and withdrew under his protection. His wartime service also brought him the Bronze Star Medal, while two Purple Hearts reflected the wounds he suffered in combat.

But the action that would define Montgomery's legacy was still ahead.

Before dawn on 22 February 1944, near Padiglione on the Anzio beachhead, German troops established three threatening positions just 50, 100, and 300 yards from Montgomery's platoon. Armed with an M1 rifle and hand grenades, he crawled through a ditch toward the nearest enemy position. He attacked alone, killing eight German soldiers and capturing four.

Rather than retreat to safety, Montgomery pressed forward. After directing artillery fire against a defended house, he attacked a second enemy position with his carbine, silenced two machine guns, and forced seven more Germans to surrender. He then advanced toward the final strongpoint despite exposure to enemy snipers. By the end of the morning, his actions had resulted in 11 enemy soldiers killed and 32 captured.

That night, while helping another American unit repel a counterattack, Montgomery was seriously wounded by mortar fragments. His Medal of Honor citation, published in War Department General Orders No. 5 on 15 January 1945, praised the courage and selflessness with which he attacked three enemy positions and inspired his men.

Following extensive medical treatment, Montgomery returned to duty in the United States. President Franklin D. Roosevelt personally presented him with the Medal of Honor at the White House in 1945. His Army Good Conduct Medal, American Defense Service Medal, American Campaign Medal, European-African-Middle Eastern Campaign Medal, and World War II Victory Medal further reflected his years of military service.

After leaving the Army in September 1945, Montgomery returned to Oklahoma and continued serving veterans through the Veterans Administration. He died on 11 June 2002 and was laid to rest at Fort Gibson National Cemetery. The Jack C. Montgomery VA Medical Center in Muskogee was later named in his honour.

Jack Cleveland Montgomery's legacy is not simply the story of one soldier defeating overwhelming odds. It is the story of a leader who placed the lives of his men above his own, demonstrating that extraordinary courage can begin with a single decision to protect others.