Richard Jesse Bailey, a native Virginian, traveled to his state’s capital of Richmond in early April 1862 to enlist his services in the Confederate army. As many from his state and community would have enlisted in a Virginian company being mustered in near his place of residence, for some reason, Richard did not do this. Instead, he enlisted as a private on April 8th, 1862 at Richmond with Company H, 3rd Arkansas Infantry, the only regiment the distant state of Arkansas sent to Virginia to serve in the Army of Northern Virginia.

As Richard’s new comrades in the 3rd Arkansas began to familiarize themselves with this Virginian, they were not only bonded through the shared experience of the bloody battles they experienced together, but the Arkansans also quickly discovered Richard’s musical talents. Due to this discovery, Richard was quickly transferred to the field and staff of the regiment as a musician and band member. He would continue to serve in this capacity until the 3rd Arkansas surrendered its colors at Appomattox Court House.

The 3rd Arkansas was apart of the Texas Brigade in General James Longstreet’s 1st Corps for most of the war, seeing their fair share of trials and tribulations in almost every conflict the Army of Northern Virginia found itself engaged. The Arkansans were even referred to as the “3rd Texas” and honorary Texans by their fellow comrades in their brigade, attributing to the 3rd Arkansas’ tenacity, efficiency, and reliability in combat.

In addition to his musical talents, Richard was an expert wood whittler. During the war and in its immediate aftermath, he carved mementos reminding him of moments he experienced with the 3rd Arkansas during the war. One of these was the “Dixie-Drinking Cup”, which Richard carved from a coconut shell memorializing the Battle of Gaines Mill On June 27th, 1862 during the Peninsula Campaign. Etched into the coconut shell is “R.J.B. 3rd Ark Regt Inf A.N.V. Gaines Mill VA. June 1862”, "Dixie-Drinking Cup”, and "Ask For The Living Water”. Another memento was a spoon, in which he carved “July 1862 Jesse”, “3rd Ark Regt Inf Hoods Texas Brig. Longstreets Corps A.N.V.”, and “Drewrys Bluff James River Virginia”. However, the most fascinating one was a wood block that Richard took from the famous apple tree at Appomattox where it was previously believed by some soldiers that Lee and Grant had met to discuss surrender. Carved into it, Richard etched "From Apple Tree Appomattox C.H. VA 1865”, "Where Generals R. E. Lee And U. S. Grant Met April 9,” and "3rd Ark Regt Inf. Texas Brigade”. Lee and Grant actually met at Wilmer McLean’s Parlor, but Richard still took a piece of the apple tree to do some whittling to memorialize his experience at the end of the war in Virginia.

During the Appomattox Campaign, Richard and the 3rd Arkansas marched along with Field’s Division of Longstreet’s 1st Corps. They engaged Federal forces around High Bridge and Farmville on April 6th-7th, and at the time of the meeting between Lee and Grant at Wilmer McLean’s parlor on April 9th, 1865, Richard and the Arkansans were trying to keep the Yankees at bay near New Hope Church. Upon receiving word of the surrender of the Army of Northern Virginia, the Arkansans surrendered their rifled muskets and battle flag. Richard was one of seven who were left in Company H, and one of only 145 officers and men of the 3rd Arkansas who remained.

After Richard received his parole pass, he remained in Virginia until he joined the U.S. Army as an engineer on July 11th, 1868. After his discharge from the U.S. Army on June 7th, 1871, he moved to Garland County, Arkansas, probably to be around some of his living comrades in the 3rd Arkansas who survived the war with him. Richard last resided in a Confederate Soldier’s Home in Little Rock in 1923. However, he only lived there for a year, as in 1924, Richard left. It is believed he was heading to Texas, but Richard was never heard of again.