Alwyn was born in Sanford, Florida, on the 13th of July 1970, and he grew up in nearby Oviedo. He graduated from Oviedo High School in 1988 and he enlisted in the US Army shortly after. Alwyn had been stationed in Korea and at Fort Lewis, Washington, in addition to deploying to Yugoslavia and the Middle East in support of the Gulf War. He was stationed at Fort Hood, Texas, and in Germany before attending and graduating from Drill Sergeant School in 1998. He served at Fort Benning, Georgia as a Drill Sergeant, before returning to Europe in 2001 with the 19th Battlefield Coordination Detachment and then being stationed with the 1st Battalion of the 18th Infantry Regiment in Germany.

Alwyn’s first post 9/11 deployment was during the 2003 invasion of Iraq but it was during his second Global War on Terrorism deployment to Iraq that would earn him the Silver Star, and later be upgraded to the Medal of Honor. The citation reads:

Sergeant First Class Alwyn C. Cashe distinguished himself by acts of gallantry above and beyond the call of duty while serving as Platoon Sergeant with Company A, 1st Battalion, 15th Infantry Regiment, 3rd Brigade, 3rd Infantry Division in Salah Ad Din Province, Iraq, on October 17th, 2005. While on a nighttime mounted patrol near an enemy-laden village, the Bradley Fighting Vehicle which Sergeant First Class Cashe was commanding was attacked by enemy small-arms fire and an improvised explosive device, which disabled the vehicle and engulfed it in flames. After extracting himself from the vehicle, Sergeant First Class Cashe set about extracting the driver, who was trapped in the vehicle. After opening the driver’s hatch, Sergeant First Class Cashe and a fellow soldier extracted the driver, who was engulfed in the flames. During the course of extinguishing the flames on the driver and extracting him from the vehicle, Sergeant First Class Cashe’s fuel soaked uniform, ignited and caused severe burns to his body. Ignoring his painful wounds, Sergeant First Class Cashe then moved to the rear of the vehicle to continue in aiding his fellow soldiers who were trapped in the troop compartment. At this time, the enemy noted his movements and began to direct their fire on his position. When another element of the company engaged the enemy, Sergeant First Class Cashe seized the opportunity and moved into the open troop door and aided four of his soldiers in escaping the burning vehicle. Having extracted the four soldiers, Sergeant First Class Cashe noticed two other soldiers had not been accounted for and again he entered the building to retrieve them. At this time, reinforcements arrived to further suppress the enemy and establish a Casualty Collection Point. Despite the severe second-and third-degree burns covering the majority of his body, Sergeant First Class Cashe persevered through the pain to encourage his fellow soldiers and ensure they received needed medical care. When medical evacuation helicopters began to arrive, Sergeant First Class Cashe selflessly refused evacuation until all of the other wounded soldiers were evacuated first. Sergeant First Class Cashe’s extraordinary heroism and selflessness above and beyond the call of duty were keeping with the highest traditions of the military service and reflect great credit upon himself, his unit, and the United States Army.

The citation for Alwyn’s Silver Star goes into a little more detail about the event, stating that he was in the gunner’s position of the Bradley and when the vehicle was hit by the IED explosion, he crawled from the gunner’s position directly to the driver to extinguish him. The vehicle’s fuel cell had been ruptured during the explosion, which explains why his clothing had been soaked in fuel. Because of his actions, the national translator and ten soldiers were recovered from the burning vehicle: of these eleven, the translator and four soldiers died, but all were injured. Alwyn suffered second and third degree burns on over 72% of his body due to his dedication to the men in the Bradley. Even during the medical evacuation to a hospital in Balad, Alwyn continued to ask about the condition of his men. The group were flown to Brooke Army Medical Center in San Antonio, Texas, and twenty-two days after the attack, Alwyn asked his sister, “how are my boys?”, in the final moments before his death at the age of 35 years old. Soon after, there was a push to advocate for Alwyn’s Silver Star to be upgraded to the Medal of Honor: what would end up being an almost thirteen-year mission.

At the time of the Silver Star award, witness statements were unable to be obtained due to evacuation for medical treatment and his battalion commander, Gary Brito, was unaware of the level of injuries Alwyn had sustained. He would later submit statements to justify the upgrade and in 2019, on the 14th anniversary of his actions, three members of Congress wrote to the Defense and Army Secretaries with a formal request of upgrade. These members were Dan Crenshaw (former Navy SEAL), Michael Waltz (former Army Special Forces), and Stephanie Murphy (former national security specialist). Secretary of Defense Mark Esper agreed that Alwyn’s actions deserved the Medal of Honor and in September of 2020, Stephanie Murphy introduced a bill, which passed unanimously, that waived the five-year statute of limitations for the consideration for the Medal of Honor for acts during Operation Iraqi Freedom. Two months later, the Senate passed legislation that set in motion Alwyn’s upgrade and in December of 2020, President Trump signed HR 8276, authorizing the upgrade of his Silver Star to the Medal of Honor.

It was assumed that the official presentation ceremony would take place prior to President Trump leaving office but it was decided that it wouldn’t happen until after President Biden took office. The long-awaited ceremony finally took place on the 16th of December 2021, when Tamara, Alwyn’s wife, accepted the Medal of Honor from President Biden in a ceremony at the White House, making him the only black recipient of the Global War on Terrorism. He is survived by his wife, two daughters (Lajada and Alexis), and his son (Andrew), who joined the Army and graduated One Station Unit Training at Fort Benning in July of 2020. Alwyn Crendall Cashe is buried with his parents and brother in the Restlawn Cemetery in Sanford, Florida.