"Prior to the attack on Pearl Harbor on December 7, 1941, Taylor spent the night before playing poker and dancing at the officers' club at Wheeler with fellow pilot George Welch, and did not go to sleep until 6:30 a.m. local time on the day of the attack. Taylor and Welch awoke less than an hour and a half later at 7:55 a.m. to the sound of low-flying planes, machine-gun fire, and explosions.
Lt. Taylor quickly put on his tuxedo pants from the night before and called Haleiwa Auxiliary air field where eighteen P-40B fighters were located. Without orders, he told the ground crews to get two P-40 fighters armed and ready for takeoff.
The new Buick was strafed by Japanese aircraft as the two pilots sped the 10 miles to Haleiwa; Taylor at times reached speeds of 100 mph (160 km/h). At the airstrip, they climbed into their Curtiss P-40B Warhawk fighters, which were fueled but armed with only .30 cal Browning ammo.
After they took off, they headed towards Barber's Point at the southwest tip of Oahu, and initially saw an unarmed group of American B-17 Flying Fortress bombers who were arriving from the mainland United States.
They soon arrived at Ewa Mooring Mast Field which was being strafed by twelve Nakajima B5N "Kate" torpedo dive bombers of the second Japanese attack wave.
Although the two pilots were outnumbered six-to-one, they immediately began firing on the bombers. Taylor shot down two dive bombers and was able to damage another before running out of ammunition (the third damaged aircraft was considered Taylor's first probable kill.
When both pilots had run out of ammo, they headed for Wheeler Field to get additional .50 cal ammo, since Haleiwa did not carry any. As he landed around 8:40 a.m., he had to avoid friendly anti-aircraft and ground fire. Once he was on the ground, several officers told Taylor and Welch to leave the planes and not return to attacking the Japanese aircraft, but the two pilots were able to convince the officers to allow them to keep fighting.
While his plane was being reloaded with the .50 cal, a flight of dive bombers began strafing Wheeler, and Welch took off again (since he had landed a few minutes before Taylor and was already reloaded).
The men who were loading the ammunition on Taylor's plane left the ammo boxes on his wing as they scattered to get away from the bombers. Taylor quickly took off, jumping over an armament dolly and the ammo boxes fell off of his plane's wing.
Both pilots realized that if they took off away from the incoming aircraft they would become targets once they were airborne, so both headed directly towards the bombers at take-off. Additionally, if the low-flying bombers attempted to fire at the grounded P-40s at their current elevation, they would risk crashing. Taylor used this hindrance to his advantage and began immediately firing on the enemy aircraft as he took off, and performed a chandelle.
Taylor headed for a group of enemy aircraft, and due to a combination of clouds and smoke, he unintentionally entered the middle of the formation of seven or eight A6M Zeros.
A Japanese rear-gunner fired at Taylor's aircraft and one of the bullets came within an inch of Taylor's head and exploded in the cockpit. One piece went through his left arm and shrapnel entered his leg.
Taylor reflected on the injuries in a 2001 interview, saying "It was of no consequence; it just scared the hell out of me for a minute." A few years after the interview, Taylor received two other slugs from his crew chief that had been found behind his seat. Welch shot down the aircraft that had injured Taylor, and Taylor damaged another aircraft (his second probable kill) before pulling away to assist Welch with an attacking A6M Zero. The attacking Zero and the rest of its formation left to return to their carriers as Taylor neared Welch.
Taylor continued to fire on several enemy aircraft until he ran out of ammunition, and both pilots headed back to Haleiwa. After landing and driving back to Wheeler, Taylor and Welch passed by their squadron commander, Major Gordon H. Austin, who noticed that they were wearing their tuxedo attire. Unaware of their earlier dogfights, he shouted at the two men, saying "Get back to Haleiwa! You know there's a war on?" The two pilots explained what they had done, and the commander thanked them.
In a 2003 interview, Taylor reflected on his actions: "I wasn't in the least bit terrified, and let me tell you why: I was too young and too stupid to realize that I was in a lot of danger."