US Navy 1st Class Electricians Mate Robert Gerald "Bobby" Oliver was born in Pensacola, Florida on October 5, 1918, the son of Gerald Augustus "Pop" Oliver (1895-1971) and Annie Mae Bayless (1898-1973). His father was born in Key West, Florida although his family made their way back to their hometown of Pensacola sometime before 1910. That year, Robert's grandfather John G. Oliver was running a "gent's furnishings store." In 1920, Gerald and Annie were living with her father Frank E. Bayless who was working as a ship's rigger and living at 1414 East Strong Street. Gerald had gone to work close by as a ship's riveter. Perhaps because his Gerald's father John was a former chief of the Pensacola Fire Department, he was able to secure employment with them as well.
By 1935, Robert was attending Pensacola High School where he was a member of the Tiger football team. He would graduate in the Class of 1937, with his brother Walker Bayless following suit in 1941. After high school he attended San Diego State College for a year and a half to play football. But whether it was the Great Depression or just looking for adventure, Robert enlisted in the US Navy on September 9, 1937, in San Diego. He was assigned to the battleship BB-43 USS Tennessee before being sent to the receiving station in San Diego on October 31, 1941. From there he was transferred to several ships in quick succession. He was on the troop transport APA-2 USS Harris on December 16, 1941, the destroyer AS-14 USS Pelias on December 26, 1941, and the submarine SS-201 USS Triton on January 15, 1942. He finally arrived on the submarine SS-269 USS Grayling on March 21, 1942.
In July 1943, he and his boat left Fremantle, Australia to begin their eighth and last war patrol. They made two visits to the Philippines, delivering supplies and equipment to the guerrillas at Pandan Bay, Panay. There, they also recorded their last kill, the enemy cargo ship Meizan Maru on August 27 in the Tablas Strait. The Navy's last contact with the submarine was on September 9 with nothing ever heard from her again. After the war, enemy records revealed that on August 27 Japanese ships witnessed a torpedo attack in the Tablas Straits, with a surfaced submarine seen in the same area the next day. Both of these correspond with the activities of the Grayling. Then on September 9, records show that a surfaced American submarine was seen inside Lingayen Gulf. At that time the Japanese cargo vessel Hokuan Maru reported a submarine in shallow water west of Luzon. The ship made a run over the area and “recorded an impact with a submerged object.” Assuming she survived the incident, no other recorded Japanese attacks could have sunk the Grayling.
Sadly, USAAC Sergeant Roy Walter Wilfon had escaped capture when the Japanese captured the Philippines in 1942. He evaded the enemy until August 24, 1943, when he was rescued by the USS Grayland off Panay Island. On September 9, he would perish along with the crew of the Grayling. Robert's first submarine, the SS-201 USS Tritron met her own fate six weeks earlier than the Grayling when she was sunk with all hands by three Japanese destroyers.
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