​​Holloway became an officer in 1943 and went on to lead the weapons platoon of Company K, 393rd Infantry Regiment, US 99th Infantry Division.

​On the morning of 16 December 1944, he was positioned in the Krinkelt Forest on the Belgian German Border. The sound of the opening German barrage could be heard on the frontline. This continued to grow, and the artillery fell around Holloway’s command post and where his troops were positioned with their mortar weapons. After this had passed, Holloway ordered his men to prepare to confront the German soldiers. With the intense and sustained bombardment, they knew this was the beginning of something big.

​The German forces shone searchlights into the sky, bouncing off the clouds and illuminating the forest in front of Holloway’s troops’ positions. They quickly clashed with soldiers of the German 277th Volksgrenadier Division. Holloway’s troops fired towards the frontline, eventually ending up firing nearly vertically, with rounds of ammunition landing close to their own positions. They couldn’t stop the wave of German infantry as it advanced beyond their own positions.

During this action, Holloway was last seen stood in the entrance to his command post, which he then fell into. It was believed he had been shot. Eventually, his men withdrew from their positions and fell back. Holloway was reported Missing in Action (MIA).

​In November 1990, following years of research and interviews with veterans of the same Company as Holloway, a search of Krinkelt Forest was conducted. Three positions were located. These were believed to be where Holloway’s soldiers had been positioned with their mortar weapons. The search was authorised and conducted by the Missing in Action project. A further position was located, believed to be Holloway’s command post. Finally, a fourth hole, thought to be a rubbish pit, was located and searched. Eventually, through careful searching, human remains were found and identified to be those of Holloway. His remains were repatriated to the USA, where he now lays at rest.

​A letter he wrote home hours before he was killed in action made it back to his family. The picture painted was a stark contrast compared to what took place hours later during the German offensive in the Ardennes.​