Major (Maj.) Kenneth Bailey joined the US Marine Corps on July 1, 1935 in Danville, Illinois, with a commission as a Second Lieutenant. Before joining the Marines, Bailey was a part of the Illinois National Guard in the 130th Infantry Regiment for three years. While serving in the Marine Corps until 1942, Maj. Bailey held many posts and positions. His first post was in Philadelphia, Pennsylvania, for basic training. Next, Bailey joined the 5th Marine Regiment in Quantico, Virginia, where he participated in ship maneuvers that took him to San Diego, California, and the Caribbean Sea. In June 1938, Bailey joined the Marine Detachment on the USS Pennsylvania. It was on this ship that Bailey was advanced to the position of First Lieutenant in 1939. After this, Bailey had several short duties. One was as a Range Officer in Quantico and another was as an assistant to the Training Officer of a Marine recruiting depot on Parris Island, South Carolina. Joining the First Marine Brigade in December 1940, Bailey was sent to Guantanamo Bay, Cuba. While in Cuba, Bailey was reassigned to the 7th Marine Regiment first, then the 1st Marine Regiment which returned to Parris Island soon after he reported to them. Bailey was promoted to the rank of Captain in March 1941. Back in Quantico in June 1941, Bailey joined the 5th Marine Regiment as the company commander, which was renamed the 1st Marine Raider Battalion in February 1942. This battalion was first sent to the Marine Corps Recruit Depot in San Diego, California, from Quantico as a stopping point on their way to Tutuila, American Samoa. Promoted to Major in May 1942, Bailey led an assault on a Japanese machine gun nest in August 1942 during the invasion of Tulagi, Solomon Islands, which marked the beginning of the Guadalcanal Campaign. Due to his bravery in pushing forward despite being injured and his calm directions to his company until they were forced to evacuate, Bailey was given the Silver Star. As the Commanding Officer of Company C of the 1st Marine Raider Battalion, Bailey moved with his unit from Tulagi to Guadalcanal, also of the Solomon Islands. It was here during the days of September 12-13 that Bailey also proved to be worthy an honor higher than that of the Silver Star.
The Medal of Honor was received by Bailey for his actions during the Battle of Edson's Ridge, and in defending Henderson Field in Guadalcanal. Maj. Bailey's company was assigned to a reserve battalion position in a field between the main line of fighting and the coveted airport. In this position, they were attacked by a strong and numerous Japanese force which attempted to unseat them from the field. After successfully repelling an attack that attempted to break through his company's right flank only an hour after they had assumed the position, Bailey continued to hold his post, improved its defense for future attacks, and expertly used all of the weapons available to him in defending his company's location. All of this was accomplished despite a fierce battle the night before that had caused a complete reorganization of his battalion. Bailey maintained his position in spite of the forced retreat of the US troops at the front line by Japanese soldiers, which he and his company were able to give sufficient cover to prevent the Japanese from shooting anyone in the back. Bailey also did much in reversing the retreat and reorganizing the troops so as to provide a strong front to the enemy once again. Regardless of the head wound he received and the enemy fire, for ten hours, Bailey and his men fought in hand-to-hand combat with the Japanese, successfully keeping hold of Henderson Field and the airport. Bailey displayed great personal valor which inspired his men to fight heroically and resulted in the repulsion of the enemy.
Though he survived the head wound inflicted while defending Henderson Field, Bailey ultimately never left the Solomon Islands. In late September, a mere two weeks after the Battle of Ebson's Ridge, Bailey was leading an attack against the Japanese along the Matanikau River on Guadalcanal when he was killed. Bailey was awarded the Medal of Honor posthumously.
Maj. Bailey was also awarded the Purple Heart, the Navy Presidential Unit Citation, American Defense Service Medal, Asiatic-Pacific Campaign Medal and the WWII Victory Medal along with the Medal of Honor and the Silver Star for his service to the US military during WWII.
A destroyer was named in honor Maj. Bailey, and was in commission from 1945-1970.
