Born in 1833 in Pike County, Alabama, to farmers, Oates grew up in a rough and tumble time. At age seventeen he fled home, fearing he'd killed his opponent in a fight. He roamed from Florida to Texas, playing cards and getting into fist fights before returning to Alabama with his brother, John, who'd gone in search of him. In Alabama he avoided his home county, believing the authorities would arrest him for his earlier brutal brawl. It was in Chatahoochee Valley, that Oates changed his lifestyle and decided to become a lawyer. He passed the bar exam and opened a law firm with John in the town of Abbeville. Oates also ran a weekly newspaper. A new man, Oates became well-respected in his community.
With his law practice growing and successful, Oates found himself handling casework on his own as his brother joined the Confederate Army. Waiting until the spring of 1861, Oates then collected a group of volunteers, calling themselves the Henry Pioneers. They made him captain as the company joined the 15th Alabama regiment, serving with General Robert E. Lee. At first they saw little fighting action, but by 1862 the regiment fought bravely in many battles. Though admittedly fearful and nervous, Oates led his men into battle with courage. He'd advanced in rank to colonel and had his men's respect.
By 1863 Oates took over the regiment and had command at Gettysburg, fighting for control of the hill Little Round Top. Advancing as best they could against Union troops, the 15th Alabama ran out of ammunition and needed reinforcements. During the 3-day battle both sides had received heavy casualties and fatalities. Frustrated, but unable to hold his position, Oates ordered a retreat. At that same moment, the Union troops charged forward, catching the 15th Alabama off-guard. While retreating, Oates separated from his brother. Later he learned that John had received mortal wounds and had died at a Union field hospital. The death of his brother and the defeat in this battle stayed with Oates for the rest of his life.
Oates continued commanding troops until he lost his right arm during a battle. Slower to heal than his previous four wounds, Oates had to quit the military. He returned to Alabama and to his law practice. Involving himself in politics, he served as an Alabama House Representative and later as an U.S. House Representative, where he served consecutively for seven terms. But before he won his U.S. House seat and while he was still a delegate to the state constitutional convention in 1878, Oates wrote of his experiences on the battlefield at Gettysburg. Many years later an editor took Oates's account and that of Union Lieutenant Frank A. Haskell and put them into a book entitled Gettysburg.
After leaving the Congress, Oates ran for and won the Alabama governorship. Though he wanted a seat in the U.S. Senate, it wasn't to be. The Spanish-American War ensued, and President William McKinley gave him a brigadier general's commission. Never seeing action, Oates nonetheless had served in the divided U.S. Army as a Confederate and then in the united army as a Yankee. After more time in politics, Oates returned to his law practice and ventured into real estate.
At the end of his life, Oates wanted a monument on Little Round Top constructed, commemorating the soldiers, including his brother, and their sacrifices. However, the Gettysburg National Military Park commissioners wouldn't agree to it. Oates took the memory of the Gettysburg battle and his brother's death with him to his own grave on December 1, 1910.
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