Oakley, Oscar

139th New York Infantry

Oscar Oakley
Sergeant, 139th New York Infantry

Oscar Oakley was born to James and Francis Oakley on January 19, 1844, in New York City. His father died not long after. While Oscar was still young, Francis moved the family to Coram and married Sheriff Richard W. Smith. Oscar, along with his brothers, Franklin and James, grew up in the Smith home and hotel, located just south of Middle Country Road and east of Route 112. According to local tradition, George Washington stopped at the hotel for a meal when he was crossing Long Island in 1790 and was served by Smith's mother, Lucille.

Oscar grew up and worked as a farmer. Eighteen years old when the war broke out, Oscar decided to fight for the cause. He enlisted with the 139th New York Infantry on August 8, 1862. Two of his good friends, Albert and Edward Bayles, also joined the regiment. They had also lost their father at a young age, something that bound these three friends together.

The regiment was organized in Brooklyn. In September, they were sent to Washington. Oakley must have impressed his superiors, for on September 9, 1862, he was promoted to the rank of Sergeant.

The regiment moved from Washington to Fortress Monroe in Virginia, located on the tip of the peninsula where the York and James Rivers meet. While there, the regiment drilled, trained and served often on picket duty. The 139th also participated in a number of raids and skirmishes with the enemy.

The regiment was assigned to the command of General Grant. During the Battle of Cold Harbor, in a futile charge against the entrenched forces of General Robert E. Lee, Oakley received a gunshot wound to his right side. It was a bloody battle, and Oscar witnessed the deaths of his two close friends, Edward and Albert Bayles. He later wrote a letter to the Bayles family detailing the sad events of that day.

Oakley, Oscar
Final Union charge at Cold Harbor. It was here that Oakley received a gunshot wound to his side.

Oakley was treated for his wounds at the field hospital at Cold Harbor, and was later transferred to the McClellan hospital at Annapolis in Maryland. When he returned to his unit in August, he was reduced to the rank of private, but no explanation was found for this demotion.

Oakley was present when the regiment participated in the action at Chaffin's farm on September 29, 1864. He was promoted back to the rank of Sergeant on October 26, 1864, a day before the regiment fought in the battle of Fair Oaks, Virginia. Oakley was also present for the assault on Petersburg until its fall on April 2, 1865.

After the war ended, Oscar returned to Coram. He was no longer content farming, and he eventually went to work for his brother, James, who was President of the Woodhaven-Rockaway Railroad.

He married Josephine DeSilva on April 21, 1888. They lived in Woodhaven, where he continued working for the railroad. The Oakley's had two children, Walter, who died shortly after birth, and Sarah Oakley (Goodrich).

Oscar Oakley died July 26, 1920, in Woodhaven, New York.

Union troops marching into captured Petersburg.

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