During World War II, O'Hooligan was in commend as part of the 90th Infantry Division (The Alamo Infantry) assigned to destroy Nazi tanks in France.. Later in January of 1944, he was part of the 5th Armored Infantry that In were central in liberating Anzio, Italy from Nazi oppression. In August of 1944, Combat, Cookie and O'Hooligan were captured by Nazi troops who sought to tie them to one of heir tanks in order to discourage American soldiers to shoot their own men. O'Hooligan was tied to the barrel of the tank, but Combat and Cookie managed to break free and steal the tank. O'Hooligan was left tied to the barrel through the entire conflict and ride home after Combat and his allies defeated the Nazis in the area.
Still a Sargent during the Korean War, O'Hooligan once more had to work with Cookie Novak. Critical of Novak, O'Hooligan thought that despite Cookie's excellent service during the previous war, he had to prove himself in battle. After a particularly sloppy battle, O'Hooligan had Cookie demoted to cook for the other troops. Cookie continued to work as a cook for D Company until the arrival of Combat Kelly, who saw Cookie return to regular combat duty.
One night O'Hooligan caught Combat fighting in a rive with Chinese gorilla soldier Yalu River Rosie. Taking both into custody, he convinced his commanding officer Major Thorn that Combat was fooling around with Rosie, landing Combat in the stockade for 30 days. Later, after much pleading from Cookie Novak, O'Hooligan agreed to give his subordinate 24 hours leave. However, when Cookie was returned to base late, he refused to believe Cookie's accounts that he was attacked and robbed by a Chinese spy, and instead believed that he was drunk and disorderly and placed Cookie in the stockade for this "infraction" as well. When Cookie was later injured in battle, the Sargent sent Cookie to the infirmary for treatment. When O'Hooligan went to check on Cookie, he was furious to find Novak being waited on hand and foot by the beautiful female nurse. When Cookie was discharged from the infirmary and was looking forward to a girlie picture being screened for the troops, O'Hooligan derailed these plans by sending him on a mission to pick up passengers. However, this punishment backfired when the passengers that Cookie was sent to pick up turned out to be the actresses from the film being screened who had traveled to Korea to visit the troops.
While assigned on a mission to fight the enemy alongside Cookie Novak, O'Hooligan reluctantly allowed Cookie to keep a dog that he befriended them on the battle field, although he believed the mutt would get them killed. However, O'Hooligan changed his tone when the dog in turn pulled them both to safety from enemy grenades, saving their lives. At base, O'Hooligan played himself up as ladies man, using photos of attractive women he bought at carnivals back home to show off to the other troops. He also teased Cookie Novak for not having a girl back home. When Cookie claimed he did, O'Hooligan challenged him to produce a picture. When Cookie succeeded (ordering one from a girlie magazine) O'Hooligan decided to put to a vote who had a picture of the most attractive woman. When Novak won, O'Hooligan noticed that the photo was ordered from a magazine from the stamp on the back. However, before he could expose Cookie as a fraud, Cookie's luck took a huge turn: A wartime photographer showed up on the base who turned out to be the very model in the picture. She verified Cookie's "claims" that she was his girl back home, cementing O'Hooligan's humiliation. O'Hooligan got back to Novak by ordering him on latrine duty, ruining a date with a photographer named Flash. However, Novak uncovered a tunnel into their base being dug by enemy soldiers and stopped this plot. When O'Hooligan tried once again to put Novak on latrine duty, Major Thorn overrode his order and sent the Sargent digging the latrines instead.
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