The following Prisoner of War letter was written by Capt. William J. Bailey, Jr. of Leon county, Florida. Early in the war he commanded the Aucilla Guards at St. Marks but when the 5th Florida was organized early in 1862, he joined that regiment as Captain of Co. G. Bailey led his company through some of the most brutal battles of the war—2nd Manassas, Sharpsburg, Fredericksburg, Chancellorsville, and was with his regiment in Lang’s Brigade at Gettysburg where he was wounded and taken prisoner in Longstreet’s sunset attack on the Union Left July 2, 1863. He spent the latter half of 1863 and most of 1864 imprisoned at Fort Delaware. History records his having been selected on 20 August 1864 as one of the “Immortal 600” Confederate officers that were used as human shields on Morris Island during the siege of Charleston. Bailey was reported to have been bounced between several prisons including Fort McHenry (Baltimore), Johnson’s Island, Point Lookout, and Fort Delaware.
In November, 1864, some 200 of the 600 were removed to a prison on Hilton Head Island where they experienced conditions similar to those they did on Morris Island. Prisoners were driven to “catching and eating dogs, cats and rats,” according to Lt. Peter B. Akers. Here, Bailey’s health became so broken by wounds and confinement that he wrote a poignant letter to the Union authorities dated December 25, 1864. Realizing that he would die in prison if not exchanged soon, he sought a parole of 60 days to return home and effect an exchange. For this special consideration, William gave his word of honor to distribute whatever the Union authorities wished (within reason) to the Federal prisoners in the South. The request was denied and Capt. Bailey died of inflammation of the lungs on March 5, 1865. He left a wife—Maria Bolling (Baker) Bailey (1836-1885), and four children born between 1855 and 1861. [Source: The Immortal 600 at Gettysburg.]
Bailey wrote the letter to Jane Eliza (Brown) Bestor (1820-1885), the wife of John Rollin Bestor, Sr. (1813-1867). This Baltimore couple had twin sons who served in the Maryland Guard that became Co. B, 21st Virginia Infantry. She seems to have corresponded with numerous Confederate officers seeking information about her sons. The Bestor brothers letters have been transcribed and may be found at 1861-65: The Bestor Brothers of Baltimore.
T R A N S C R I P T I O N
Pt. Lookout, Maryland
March 18th, 1964
Mrs. Bestor,
Madame. Yours of the 16th inst. to Lt. Adams 1 has been received & finding it from you, I took the liberty of reading it & determined to write you. Lt. A. left here on the 3rd inst. for City Pt. & I have rec’d a note from him at that place in which he said that he expected to leave for Richmond every moment. I presume in this he is enjoying all the sweets of a dear home surrounded by all the loved ones most dear to him. He was particularly fortunate in being one of the chosen few. I have heard him speak so often & so kindly of you that I feel that I am acquainted with you & therefore taken the liberty of answering your letter. I am much obliged to you for the kind sympathy expressed for me. Should I reach Richmond soon, will do myself the pleasure of writing to your sons. The exchange is still going on in an informal way. 50 officers & 600 men left yesterday. The members of Lt. A.’s old mess join me in kind regards.
Respectfully, — Wm. Bailey, Capt. 5th Fla. Regmt.
1 Possibly 1st Lt. Samuel F. Adams, Jr of Co. E, 45th North Carolina Infantry. He was taken prisoner during the retreat from Gettysburg, held at multiple camps, and transferred to Point Lookout, Maryland. He was officially exchanged on 6 March 1864.
