Dixie Boy - Union Spy (Article 82)

“Some in the South called me a turncoat and some called me a traitor. These are untruthful. I stayed loyal to the United States and it was my region that turned on my country.” – Philip Henson

He was born in Alabama in 1827, worked along-side slaves and, for a while, even became a slave overseer; but he failed miserably at that job. He was accepted among various Indian Tribes because he had earned their friendship with his respectful attitude toward their culture. He became a successful merchant who, as the Civil War broke out, arranged to be hired by a friend in a special position which exempted him from being drafted into the Confederate Army. It was not the fear of battle which drove him to gain the exemption, but it was his anti-slavery and anti-secession views. He said that, “I was home with my people in Mississippi but I could not serve the secessionists. I swore an oath to the Union because I believed in it.” 

 So, Philip Henson became a spy, and risked his life to serve the Union cause, while he continued to live among his neighbors.

 As a child, Henson traveled throughout Texas, Kansas, and the Indian Territories with his father, a career Federal Indian Agent, who served as a liaison to various Tribes. However, unlike many Indian Agents, his father was known as dedicated, fair, and honest in his dealings with the Natives. His father’s earned respect by the Tribes carried over to Philip and he was largely educated along with Native children in schools overseen by his father. In turn, Philip respected the native cultures and was able to move freely, and comfortably, within Indian territories for the rest of his life.

 His father died when he was only twelve and, since there was no federal pension system at the time, he had to find work to support his mother and younger siblings. He found a part time job as a postal carrier and, as did many poor White children in the South, he also worked on several large plantations, often alongside slaves. At one point when he was about twenty-one, a plantation owner offered him a new job as overseer of slaves, usually a step-up for a White field hand. But Philip did not have the aptitude, or attitude, to use the harsh measures which were common to drive the slaves to work harder and faster. He quickly realized that he was just not cut out for the job and notified the owner that he must quit. Instead, the plantation owner, who knew that Philip was smart and honest, offered him a different job. It turned out that Philip was good at managing the transportation of crops to market and selling them at auction; so, he continued to be employed, but in that more genteel capacity. However, he was still involved in a business that derived profits from the toil of slaves, and that fact continued to bother him. He later said, “I only regret that I was near thirty when I saw that slavery had no place. Before then I was the same as any slaver.”

 Until he decided to strike out on his own.

 He left Alabama when he was about thirty years of age, to become a travelling trader in Kansas, the Indian Territory (now Oklahoma), and the New Mexico Territory. After three reasonably successful years living out of a covered wagon, he had accumulated enough money to return home to start a general merchandise business. He opened a store in Corinth, Mississippi, close to his old home in Alabama, married a young woman he had known before his travels, and settled down to a stable family life.

 But the secession of the first seven Southern states, including Alabama and Mississippi, in early 1861, interrupted his plans.

 Henson’s experiences working with and then overseeing slaves had convinced him that slavery was wrong and he believed secession was a mistake. However, since neither position was popular in Alabama or Mississippi in 1861, Philip only shared his opinions with a few close friends. Although he did not volunteer to join the new Confederate Army, as did many of the other young men in the area, his loyalty to the Southern cause was not yet questioned and he continued to operate his successful mercantile business.  His life began to change, however, when the new Confederate government imposed a draft to conscript men into the Army, and Philip Henson, at thirty-four years old, received his draft notice.

 There were numerous exemptions to the Confederate draft including the first-born sons of plantation owners, anyone who owned more than twenty slaves, and certain government positions; but Philip did not qualify. Fortunately for him, there was also an exemption for an overseer of plantation slaves, and an old friend who owned slaves, but who was not in favor of secession or the draft, officially hired him as an overseer. It was a curious arrangement because his new employer knew that Philip had failed at that type of job before, but he never expected him to fulfill the duties. And, the ruse worked. With his draft exemption in place, Philip again focused on his business and family. Obviously, the Confederate officials still did not suspect that he opposed both slavery and secession because, based on his former work as a postal carrier, Philip was offered and accepted the position as a supervisor for the Confederate Postal System. Which was also exempt from the draft!

 His new duties allowed him to travel throughout the South and, on a trip to Texas, he met and became friends with that state’s former Governor, Sam Houston, who had opposed secession by Texas. Houston had warned Texans to not join the Confederate States, which he correctly expected would eventually be defeated by Union forces. However, Texans chose to secede and Houston’s refusal to sign an oath to the Confederacy had resulted in his ouster as Governor. Philip confided in Houston that he could not support the Confederates and would be willing to actually aid the Union if he knew how. Sam Houston suggested that Henson travel to Illinois to meet officials who Houston knew might have use for a dis-satisfied southerner, but one who still enjoyed the favor of the Confederate government. Through those initial contacts, Henson was introduced to a young Army Colonel, Ulysses S. Grant, who would soon be dispatched to Tennessee to engage Southern forces. Henson swore an oath to the Union and was soon providing information to Colonel Grant which would prove valuable to his mission.

Philip Henson had agreed to become a spy!

 One of his early efforts on behalf of the Union was to contact a small group of Alabamians, self-named the Mossbacks of Nickajack, who opposed the Confederacy. The Mossbacks had systematically hindered shipments of Confederate supplies northward into Tennessee for several months, aiding the Union without actually being affiliated. Henson introduced their leaders to Colonel Grant and the Mossbacks became an integral part of his forces, and later formed into the First Alabama Cavalry, serving under Union General William Sherman.

 Incredibly, Henson continued to avoid detection by his Confederate postal system superiors and was still able to travel throughout Tennessee, Mississippi, and Alabama in his official capacity. We do not know if he was asked, or chose on his own, to visit Vicksburg, Mississippi. The fortress city overlooked the Mississippi River from a bluff and guarded that waterway route which was so vital to the flow of goods to the Southern Army. While in Vicksburg, Henson scouted out the city’s fortifications, which he reported to (now) General Grant. We can assume that the information about Vicksburg’s defenses was helpful to Grant as he decided to conquer the city by a siege rather than by more direct attacks which he had tried earlier. The strategy was successful and the large Confederate force, and the town’s citizens, surrendered in July, 1863.

 By early 1864, several Confederate officers had become suspicious of Henson’s frequent visits near their lines and he was finally arrested. Without any evidence, but with the suspicions of several officers he trusted, Confederate General Nathan Bedford Forrest had him sent to Mobile, Alabama, imprisoned, placed in chains, and held in solitary confinement. Henson continued to deny that he was aiding the Union, despite mental and physical torture at the hands of his guards. Occasionally, an officer would enter his cell and tell him he would be shot that day unless he revealed his sources and supporters. Although he was reported to have said Henson was, “The most dangerous spy operating within the Confederacy,” General Forrest could never prove that Henson was disloyal and never brought any specific charges against him. After about six months of horrific confinement, his guards moved him into a general stockade and began to pay less attention him; and he quickly escaped.  He mingled with different Confederate units for several weeks as he made his way north toward General Grant’s lines. He finally slipped into Union held territory, just outside Appomattox Courthouse in Virginia, and reached General Grant’s headquarters. One of Henson’s contacts in the Union Army, upon seeing him safe in the Northern camp said, “Well, Phil, the damn rope has not been made yet to hang you!”

General Grant appreciated Henson’s contributions and, although his usefulness as a Union spy was over, Grant gave him a brevet (temporary) commission as Major and assigned him to duties similar to an Inspector General, where his keen observations again proved helpful.

 Then, everyone’s world changed; President Abraham Lincoln was assassinated!

 Although the official inquiries were headed by Secretary of War Edwin Stanton, General Grant asked Henson to conduct an “unofficial” investigation and to report any finding directly to him. We do not know if Henson uncovered any information helpful to the official assassination investigation; and (technically) his service to the Union ended when Grant resigned as Commanding General to accept the nomination of the Republican Party for President in 1868.

 After the Civil War, Henson was denied a pension by the War Department because he would not provide details of his service, and he never asked former General Grant to verify his assignments for the Union. But, when Grant became President in 1868, he again asked Henson to lead various investigations and conferred the rank of Lt. Colonel to assure Henson had wide access to military and civilian files. As part of his duties, Henson also investigated any threats to President Grant; a precursor to the Secret service.

 After Grant’s second term ended, the public began to become aware of Henson’s service on behalf of General (and President) Grant. Soon, he was in demand as a public speaker and was considered very entertaining as he often used his talent for mimicking dialects as he told stories of famous (and infamous) people he had encountered. Also, sometime in the 1870s, Henson decided to let his beard grow, “until it stopped.” And he did! In 1898, one newspaper article reported, “As many came to see his six foot long beard as came to hear him speak. It was a wonder he could move his jaw.” There are no known photographs of Henson with a beard that long, but there is a sketch used for advertisements and the cover of programs for his speaking engagements. The drawing may have exaggerated the beard and he could have even added extension hair; but the long beard added to his mystique and celebrity status.

 Henson, beard and all, was able to make a good living by giving speeches about his exploits; however, he provided only sketchy anecdotes, leaving his audiences then, and historians today, wishing he would have divulged more. He never gave any details about his investigation into Lincoln’s assassination because, “The General never gave me permission to talk to any other man.” He told one of his sons, “The damn thing of it was to track the trail of blood, bodies, and bucks until it got me there”

 Philip Henson died at age 84, taking most of his private conversations with Grant to his grave.

 Henson once said that he marveled at his survival during the war, including his capture and harsh incarceration by Confederate General Bedford Forrest. He told an interviewer, “I do not know how, but I believe God was with me and preserved me for what I had to do. I never felt a fear of death. When I was ordered to be shot once (by an underling of Forrest), I told my wife that I did not believe I would be shot, but if I should be, I was ready to die for the cause, as my work would be finished.”

 For his speaking engagements, Henson used the tag-line “Dixie Boy, Union Spy.”

And, he was truly both!