Blackburn graduated from the United States Naval Academy in 1933 and after becoming a Naval Aviator found himself as a flight instructor in 1941 when the United States entered World War II.
Lt. Blackburn was anxious to get into a combat unit, but was relegated to flying the F2A Buffalo at Opa-locka, Florida near Miami. After several requests for combat assignment, he received orders in July 1942 to organize VGF-29 as commanding officer and report aboard the new escort carrier . VGF-29 was equipped with the F4F-4 Wildcat. Blackburn assembled a ready room of mainly brand new ensigns fresh from winning their wings at advanced flying school at Corpus Christi. Luckily he had the assistance of a combat veteran from the recent Battle of the Coral Sea, Lt.(jg) Harry "Brink" Bass who received the Navy Cross for his attack on the . Blackburn set up operations at a remote field at Pungo well away from the brass and traffic at NAS Norfolk and was soon promoted to Lieutenant Commander. Pungo suited Blackburn fine as he wanted an undisturbed environment to get the squadron acquainted with the Wildcat and ready for deployment and the combat likely to follow.
The squadron embarked aboard USS Santee in October 1942 to participate in Operation Torch, the Allied invasion of North Africa. Arriving in the waters off Morocco on November 6, VGF-29 flew first combat mission on 8 November but could not find their target, and poor weather and damaged homing equipment aboard Santee forced them to ditch or force-land their Wildcats. Blackburn floated adrift in a liferaft for 3 days before he was spotted by a destroyer and rescued. Thus ended the inauspicious debut of VGF-29 and Blackburn's first combat deployment. Shortly thereafter, Blackburn was ordered to stand up a new squadron.
Blackburn stood up VF-17 on January 1, 1943 at NAS Norfolk. It initially had a few SNJ trainers and F4F Wildcats awaiting delivery of the first F4U Corsairs in February. It was the second Navy fighter squadron to receive the F4U-1 Corsair and became most successful of them all after a combat tour in the Solomon Islands. Blackburn wanted to motivate his pilots with a squadron insignia which would live up to the Corsair name and chose the skull and crossbones and the name "Jolly Rogers". Harry Hollmeyer, as squadron pilot conceived the original design, which was painted on the cowling of the Corsairs that were also known as "hogs" due to their long noses. Blackburn named his Corsair "Big Hog" and together with his executive officer, Roger Hedrick embarked on an intensive training program to get his squadron ready for the combat that lay ahead for the planned deployent to the Pacific in August 1943. Again, he chose a remote field well away from Norfolk to operate as he saw fit and away from prying eyes of the senior leadership.
The squadron was assigned to deploy aboard and worked hard to adapt the F4U Corsair to the carrier environment, which necessitated some design changes, resulting in the F4U-1A model.
The Jolly Rogers deployed to the Pacific, but upon arrival there the Navy decided to initially land base its Corsairs and the squadron flew to Guadalcanal on October 26 where it received orders to begin operating out of Ondongo (which means "Place of Death") on the island of New Georgia in the Solomon Islands. Their arrival on the 27th was just in time to participate in providing air cover for the landings at Torokina, near Empress Augusta Bay on the island Bougainville on 1 November, which drew attention from the considerable Japanese presence at their bastion of Rabaul. Blackburn and his jolly Rogers were assigned the high cover mission for the landings and ran into a wave of Japanese Val dive bombers escorted by A6M Zero fighters. Blackburn downed 2 and the squadron 3 more in their combat debut.
On November 8, 1943, the Jolly Rogers faced their biggest test to date when 6 Jolly Rogers faced an attack of 15 Japanese Val dive bombers escorted by 24 Zeros. Hedrick launched with a flight of 8 Corsairs, but lost 2 when they aborted. In the engagement, VF-17 downed 3 fighters and damaged 4 others with no losses. In its two tours of duty in the Solomon Islands, VF-17 had 152 aerial victories and produced 11 aces. Blackburn ranked third with 11 victories behind Hedrick with 12 and Ira Kepford who led the squadron with 17. VF-17 finished its last combat tour in the Solomons on May 10, 1944 and many pilots were reassigned.