CONFEDERATE BATTLE FLAG OF THE 37TH MISSISSIPPI INFANTRY, ENGAGED AT PORT HUDSON AND VICKSBURG

“On the 28th day of July 1864, we turned back to meet General Sherman at Peach Tree Creek…We lost many brave, good, and noble men in this conflict, amongst whom was Wyatt Jones, our color bearer, from Co. K, 37th Miss. Regiment. He was in advance of our Company and was shot as he mounted the enemy's works. There was not a better soldier, nor a braver man in the Company than Wyatt Jones…”

- Recollections of the Civil War by J. B. Lightsey (Jasper County Review, January 2, 1908)

43¼” on the hoist and 53¾" on the fly. Mobile Depot pattern. c. 1863. Completely hand-sewn and constructed on a field of red wool English bunting, intersected by a 6½" to 7" blue wool bunting cross. The cross has twelve white cotton stars inserted into the fabric three on each arm. The cross is trimmed with two layers of 1¼" off white cotton fabric. The leading edge of the flag is turned to the reverse to form a 2" pole sleeve. Appliquéd on the obverse only, in two rows with 2" white cotton letters, "37th Reg: Miss./Infantry.”

An important flag used by a hard-fought regiment that likely bore witness to the death of at least one color bearer, as well as many pivotal engagements in the Civil War’s Western Theatre. This remarkable artifact is offered here publicly for the first time since it was initially sold by the family of Colonel Orlando S. Holland, commander of the 37th Mississippi Infantry. Recently conserved and framed in a museum-quality frame, this flag deserves a prominent home. 

The 37th Mississippi Infantry Regiment was formally organized on April 28, 1862, in Columbus, Mississippi. Composed primarily of men from the counties of Lowndes, Monroe, Noxubee, and Chickasaw, the regiment was placed under the early command of Colonel Robert McLain and would quickly develop a reputation for tenacity. Pvt. James W. Smith, reflecting the intense sentiments among its ranks, is recorded as writing shortly after his enlistment in the 37th MS: “Let me liberate my home from the varlet’s tread, and then my country shall be freed from the fiendish vandals” 

After a period of initial training and drill, the 37th Mississippi was assigned to General Dabney Maury's Division and later became part of Brigadier General John D. Martin’s Brigade in Major General Mansfield Lovell’s Division. Early in its service, the regiment participated in defensive operations in North Mississippi, engaging in numerous skirmishes and strategic movements aimed at repelling Union forces.

In late 1862 and early 1863, the 37th Mississippi became actively involved in the Vicksburg Campaign. It was during this time that Orlando S. Holland was elevated to the rank of Colonel. The regiment fought at the Battle of Chickasaw Bayou in December 1862, successfully helping to repel Union assaults. It subsequently participated in the Battle of Port Gibson on May 1, 1863, where it played a vital role in delaying the Union advance, despite being heavily outnumbered and sustaining significant casualties.

On May 16, 1863, the regiment endured its fiercest engagement at the Battle of Champion Hill (also known as Baker’s Creek). Here, fighting alongside other Mississippi units, the 37th Mississippi sustained severe losses while valiantly defending their position against overwhelming Union forces, providing critical cover for the Confederate retreat to Vicksburg. Shortly thereafter, the regiment was besieged within the defensive works at Vicksburg, experiencing 47 days of intense bombardment and deprivation until the city's surrender on July 4, 1863. Following the surrender, the regiment was paroled and later exchanged, returning to Confederate service by late 1863.

In 1864, the regiment was transferred to General Joseph E. Johnston’s Army of Tennessee and participated actively in the Atlanta Campaign. At the Battle of Peach Tree Creek on July 20, 1864, the regiment executed an assault across difficult terrain under heavy enemy fire, temporarily disrupting Union lines.

Notably, it was at the Battle of Peach Tree Creek where color bearer Wyatt Jones was killed after advancing the 37th Mississippi’s flag, very likely the flag offered here, in advance of the main Confederate line.

Colonel Holland would write in his battle report describing Jones’ actions: “Ensign [Wyatt] Jones distinguished himself conspicuously [and] gallantly planted his colors upon the enemy’s works considerably in advance of the regiment, but I am pained to report that after storming the enemy’s works and engaging his second line of battle this gallant Christian soldier was killed by a minie ball. I respectfully request that his name be forwarded to the War Department to be inscribed upon the Roll of Honor.” (Hood, S. 2014. Pg. 74. Lost Papers of Confederate General John Bell Hood. Savas Beatie)

The 37th Mississippi continued fighting through the grueling battles in Tennessee, including the Battle of Franklin on November 30, 1864, and the Battle of Nashville in December 1864, enduring severe hardships and significant casualties. Following the Confederate defeat at Nashville, the regiment retreated southward, joining General John Bell Hood's army in a difficult march through winter conditions.

The final months of the war saw the 37th Mississippi Infantry Regiment taking part in the Carolinas Campaign against Union forces under General William T. Sherman. Engaging in multiple smaller battles and skirmishes, the regiment continued to demonstrate steadfast resolve until it finally surrendered along with the remnants of the Confederate forces at Durham Station, North Carolina, on April 26, 1865.

The flag itself has been expertly conserved by its most recent caretaker and is in stable, display-ready condition. Within the quadrants of the main field, careful examination reveals the faint outlines of once-applied battle honors, including "Port Gibson" (in an arc), "Baker's Creek," and "Vicksburg," with subtle indications of an additional honor in the header quadrant. In a report that accompanies this piece, noted flag authority Fonda Thomsen speculates these honors were initially lightly sewn at select points rather than fully stitched.

Orlando Stinson Holland (1826-1875) began his career as a newspaper editor in Enterprise, Clarke County, Mississippi, where he established himself as a prominent figure in the community prior to the Civil War. During this time, he is referred to in the papers of Jefferson Davis as being known to him as a political acquaintance. At the outset of the war, Holland enlisted as a 1st Lieutenant in Captain Patton's 5th Mississippi Volunteer Regiment, known as the Mississippi Boys. This unit later became Captain Patton's 1st Mississippi Infantry Regiment, Company K, commonly referred to as the “60-day Army of 10,000.” When this short-term regiment was disbanded upon the expiration of its enlistment period, Holland promptly re-enlisted as a Private in the 37th Mississippi Infantry, Company D, famously known as the "Enterprise Tigers."

Holland was quickly elected Lieutenant Colonel on April 18, 1862, at Columbus, Mississippi, and subsequently promoted to Colonel on October 4, 1862, at Snyder's Mill near Enterprise, Mississippi. He served notably in several key engagements throughout the war until his parole on May 2, 1865, in Greensboro, North Carolina.

After the war, Colonel Holland resumed his editorial career, relocating to Columbus, Georgia, where his outspoken editorials and political commentary drew both support and intense criticism. On March 30, 1875, he was murdered on the streets of Columbus by a part-time policeman who fled to Alabama, evading justice. Although a warrant was issued for the killer, it was quietly dropped. Holland's brother, Jim Tom Holland, publicly labeled the murder politically motivated, a sentiment echoed by the coroner’s inquest, which described his death as a deliberate assassination. Holland’s obituary remembered him as a "high toned and honorable gentleman."

Note: This lot cannot be packaged and shipped in-house. Successful bidders winning items marked as being packaged and shipped by a third-party service are responsible for paying the third party directly. We are happy to offer complimentary drop-off service to local third-party packing/shipping companies in Columbus, Ohio.

[Civil War, Union, Confederate] [Flags, Patriotic Textiles]

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