Will Montgomery: A
Mississippi Scout and Skirmisher
Montgomery, Confederate scout and
skirmisher from Edwards, wrote his memoirs of the war
in 1916 at the age of seventy-two.
Photograph courtesy of Sidney
He was eighteen, a veteran of
fighting in Virginia and not fully recovered from a crippling knee
disease. The news that Grant's army was marching toward his Hinds
County, Mississippi, home reached Will Montgomery early one May morning
in 1863 as he was about to go hunting. With his gun already loaded and
his crutches tied to a red blanket behind his saddle, Will bade his
mother, father and brothers farewell and rode off to meet the enemy. For
the next two years, he was seldom more than a short ride away from his
home, yet as a cavalry scout and skirmisher, he never again slept
beneath his parents' roof.
His account of those years, written in 1916 when he was
72, offers a fascinating glimpse into the life of an extraordinary
Mississippian who lived in extraordinary times. Old men who write their
memoirs many years after the fact may have a tendency to confuse the
chaff of heroism with the wheat of the reality of their actual exploits.
However, possible hyperbole aside, Montgomery's memory seems to have
been as clear as his mind, so that many of the stories of his exploits
fit with and add dimension to historians' accounts.
William Alexander Montgomery grew up on a large farm on
Fourteen Mile Creek, between Edwards Station and Raymond, Mississippi. A
handwritten biographical memoranda in the Mississippi State Archives in
Jackson, signed by W. A. Montgomery, Jr. and dated October 4, 1915,
provides interesting information about his family background. His
father, W. A. Montgomery, and an uncle, A. K. Montgomery, each married
sisters who were among the eleven daughters of General William Moore of
Mulberry, Tennessee. Will Montgomery grew up hearing stories about the
deeds of his ancestors. Will's paternal grandfather Charles Montgomery
rode with Francis Marion in South Carolina during the Revolution.
Marion, the "The Swamp Fox," was young Will's hero. His maternal
great-grandfather William Moore, Sr., was a Kentucky pioneer and
Indian-fighter whose son, General William Moore, fought with Davy
Crockett under Andrew Jackson and was a close personal and political
friend of James K. Polk.
Will's life was typical for his times and his family's
station in life. He describes himself in his memoirs as "fond of
horses, guns, and dogs as a boy," and "a reckless rider of
indomitable energy." Along with his brothers and several cousins, he
received his early education at home under tutors employed by the
Montgomery family. He mentions J. M. Leet of St, Louis and John Brady,
who prepared him for entrance into college as a sophomore before he was
sixteen years old. Following family tradition, Will attended Union
University in Murphreesboro, Tennessee, near his paternal grandfather's
home, just as General Moore's son, William Lawson Moore, had been
educated at Center College in Kentucky, near his mother's relatives. His
grandfather often visited Will and his cousins there.
When the Civil War began, sixteen-year-old Will was
summoned home from school. He volunteered for a three-year term in the
Hinds County Light Guards, but his father persuaded him to join the
Raymond Fencibles, a twelve month company of the 12th Regiment,
Mississippi Volunteers, instead. He was with them in Virginia when he
fell ill and had to return home. No one expected that he would see
further military service, but the Confederate commanders were happy to
have a scout, even a crippled one, who knew every creek, woods, and
bayou in the vicinity.
On the evening of May 12, Colonel Gates, the commander
at Edwards, sent Will with a squad of men to burn the bridge on Fourteen
Mile Creek above the junction of Baker's Creek. At ten that night, after
burning that bridge and several others, they hid and waited for the
approach of Grant's army. During the night, seven or eight Negroes who
thought the party were Federals offered to take him to the place where
their master was hiding in the woods. Without telling them who they
were, Will Montgomery sent a courier to a nearby plantation for six axes
and set the men to work felling trees to make a breastwork for the few
Confederates there and to serve as an obstruction to the enemy.
At dawn the head of the advancing column appeared,
unaware of the Confederates' presence. When the advance of the column
was within fifty feet of the burned bridge, Will drew down on the front
horseman. The Federals charged toward them three times before they
discovered the bridge no longer stood. Although under constant fire from
Federal rifles and artillery, the Confederates made their way into the
woods where their horses were hidden and made their escape.
In the meantime, Major Bova of the 20th Mississippi, hearing the
gunfire, took two companies to attempt to rescue the bridge burners. He
lost twenty men in taking the position Will had just left, only to give
it up a moment later, seeing it was certain death to stay.
On the morning of May 12, prior to Will’s burning of
the bridge at Fourteen Mile Creek above the junction of Baker’s Creek,
General Gregg's guns were heard at Raymond, where he made a desperate
stand against the corps that advanced by the Utica Road. Perhaps, as
Will Montgomery wrote in his memoirs, if General Grant had not been
detained there as he was, for the whole of the day, he would have come
on to General Gregg from the rear, and captured his whole army.
After the Battle of Raymond, Will Montgomery placed himself under the
command of Colonel Wirt Adams, for whom he soon became chief scout. For
a second night, he had neither sleep nor food for himself and his horse,
but he and Captain Canty of the 20th Mississippi struck up a friendship
as they went to Bolton to try to protect Confederate stores there.
Two nights before the Battle of Champion Hill as they slept in an open
field, the Captain told the young scout, "We are going to have a
great battle near here and among the slain I am to be numbered.” He
added that on his death Will was to take the fine gray horse he was
riding to use as his own during his further service for the Confederacy.
The next morning, Canty sent Will to Edwards with
dispatches. The next time they met it was on the battlefield of Champion
Hill, when Canty fell at the head of a dismounted company he was leading
into battle. A few moments later and not 75 yards from where Canty fell,
Montgomery was thrown from his horse. With crutches still tied on to the
red blanket behind the saddle, his horse dashed wildly toward the
advancing and victorious line of the Federal Army.
Seeing his riderless horse, everyone assumed that Will
Montgomery had been wounded, killed, or captured. His brother Lawson
Rochester ("Ches"), fifteen, risked his life to ride across the scene of
battle in search of Will. In the meantime, unable to walk or run without
his crutches, Will faced toward the enemy and commenced firing. Wirt
Adams found him there and urged Will to take his own horse, which Will
refused to do. About that time, Will's horse came running back and was
caught by Colonel Adams' adjutant. Amidst a hail of gunfire, all three
managed to escape from the field of battle, and the brothers were
That night, with the Federals on the same side of the
Big Black River as the retreating Confederate cavalry, the men slept
under arms with bridle reins in hand. Instead of following Pemberton
into Vicksburg, where he knew there would be no corn for his horses and
the cavalry could be of no use to a besieged city, Colonel Adams made
his report to General Johnston.
During the siege of Vicksburg, Will scouted for Adams,
who let him come and go as he pleased. His leg improved rapidly, and
soon he was able to walk without crutches. A few days before the fall of
Vicksburg, Will Montgomery was among the many who undertook the
hazardous task of carrying communications from General Johnston to
General Pemberton. He was hiding in a sink hole within the enemy lines
when the suddenly silent guns made him know that Vicksburg's war was
over. By night he made his way back across the Big Black and joined
Johnston again at Edwards on July 5th, where he was sent to find out the
strength of the force that was encircling Jackson.
Soon after General Johnston evacuated Jackson, Will went to visit an
uncle and was told that his ill mother was staying at an elderly aunt's
house in Madison County. In the family's absence, some Federal soldiers
had rifled the Montgomery home, taking what they would. Ironically, the
commander of those forces was Milton Moore of Mitchell, Indiana, a
cousin of Will's mother, who was unaware that the property belonged to
As a scout, Will Montgomery "became a terror" to the stragglers and
foragers from the Federal lines, capturing many, and frequently
deliberately engaging them in skirmishes. He and his men usually slept
in the woods with blankets wrapped around them and saddles for pillows,
lest they be surprised by the Federals. They used any kind of mounts
they could get.
Once, on an urgent errand, Will rode his sorrel horse,
"Old Cleveland," hard for 21 miles. Then, "although he was
pretty much jaded from the dash," the horse took Will eight miles
further by eight o'clock that night. One of his scouts rode "a very fat
chunk of a pony" that Will considered very slow. But with Yankees in hot
pursuit, "Old Pete laid his ears back on his mane and proved to us
that no one knows how fast a mule can run when frightened."
Montgomery in later years.
Photograph courtesy of Sonny Montgomery
They also had a variety of weapons. Will's cousin Ed
Montgomery carried a shotgun loaded with "blue whistlers," while
Will's old Belgian rifle used shot and ball. In one encounter, Will and
his men captured seven horses, seven carbines, and fourteen pistols. He
also took arms from "carpetbaggers" who had come South to work
seized plantations in the hope of making cotton to obtain the high price
of one dollar a pound. Included were some Winchester rifles, the first
sixteenshooting rifles Will had ever seen.
Will found himself crossing the Big Black River so
often that he hid a small boat on the east bank for that purpose. Many
times he had to swim his men's horses over because they declared they
would drown if they tried it. Once, when he needed to cross from the
west side, he stripped and swam over, leading his horse by the reins.
When he reached the other side, Yankees started after him, and Will lost
his bundle of clothes. Eluding his pursuers, he hid in the woods and
made a hole in his blanket, which he then pulled over his head. It
served as cover until he obtained more suitable attire, and was the
subject of much laughter among his fellows.
On one visit to his grandmother's, where his family was
then living, Will found that the Federals had captured his brother Ches,
along with J. M. Selser, one of Will's scouts, and all of Will's horses.
He decided to make a raid on the Federal lines to capture other horses,
and while he was at it, to attempt to burn the gunboat Indianola, which
lay aground not far away.
With the six men now left him, Will crossed the Big
Black, only to find a large Federal body guarding the gunboat. On their
way back, a force of eighty Federals caught up with them at two o'clock
in the morning. "Halt!" cried the foremost Federal horseman. He drew
down to fire, but his gun failed to discharge, and Will and his men
managed to escape under the cover of darkness. They finally lay down at
the head of a cane ravine in an old field so that their tired and hungry
horses might feed on the cane as they slept.
The next morning, wanting a fresh mount, Will
Montgomery persuaded an old man who thought that he was a Federal raider
to part with a fine black horse in exchange for his own. He left on the
horse, singing "Come along boy, I tell you don't stay for the Yankees
are coming along this way." Then, in a bend of the road, Will and his
small group were suddenly confronted by the Federals they had eluded the
night before. called out, With guns leveled, the commanding officer
"Hello, Montgomery, we have got you at last!"
A report had been circulating that the Rebel scout
Montgomery had been outlawed and orders issued for him to be shot
whenever captured. Will drew down a Colt's revolving rifle that stood in
front of him on the saddle, and as he attempted to fire, Turner Echols,
the scout closest to Will, knocked the muzzle up, exclaiming "My God,
what do you mean!"
At that, both instantly wheeled their horses and ran;
none of the shots fired at them took effect. To the gate a hundred yards
in front they galloped and against it under full speed they went. The
gate fell to pieces, but their horses stood stunned for a moment, which
brought the Yankees close enough for Will to hear the whiz of the
officer's saber as it flashed over his head. The horses recovered and
galloped on until they reached a fence they could not jump, and both
riders fell. Under fire, they reached a thicket, but Will's bad leg gave
way, and both men were captured.
Jailed in a dark cell in Vicksburg that night,
uncertain of his fate, Will began to sing "Tis Midnight on the Stormy
Deep." He was interrupted by a voice in the hall he recognized. It
was J. D. Selser, the scout captured in the raid Montgomery had sought
to avenge. From him he learned that his brother Ches had escaped from
the Yankees by swimming the Big Black and walking barefoot through
dewberry vines and bamboo.
After being tried as a spy, Will and some two dozen
other Confederate prisoners were put on a ship and sent, under sealed
orders, up the Mississippi bound for a prison in Alton, Illinois. Before
he left, Will gave the heavy double-breasted coat his mother had made
him to a man remaining in prison in Vicksburg who would need a warm
coat. In return, he took the man's light jacket, which would be better
to swim in.
The second night of the voyage, Will and Echols and
another man faked sleep, then when the guards' backs were turned, they
jumped overboard. In the fog and darkness, Will could not see or hear
what happened to the other two, but he made the shore safely in Bolivar
County near the mouth of the White River, on Island 66 near Memphis. He
rested a few days, laid up with the leg that had caused him so much
trouble the day of his capture. After buying a small white mule by note,
he made his way to Adams' Cavalry camp near Clinton, Mississippi. From
there, he arrived at his grandmother's house about seven the next
His little brother Charlie was on the gallery steps
holding his pony, ready to start to the Federal camp at Black Bridge in
search of information of his brother Will. His mother stood beside him,
weeping as she gave him instructions on what to do. They had been told
that Will had jumped off the boat and was shot, and General Osterhaus
had promised Mrs. Montgomery to send her the particulars of his death
In the unfamiliar short jacket and riding the little
white mule, his family did not recognize Will until he said "Good
morning," to them. A joyful reunion followed with all except his
father, who had gone to look for Will along the river bank.
Staying only long enough to take breakfast with his family, Will went
back to work again, determined to raise a force to raid the Federal post
at Red Bone. At that time, wearing Yankee blue himself, he met a squad
of Yankee soldiers dressed as Confederates. He drew his pistol and waved
back as if his men were with him and called an order to charge, and as
the Yankees scattered, he made his escape.
In another skirmish, as he rode, Will was drawing his
rammer from his old Belgian rifle, which he had sawed off to be about 28
inches long, when he heard a call to halt. He looked around to see a
Yankee pointing a pistol at his head. They were both riding fast, and as
Will raised his gun to strike down the weapon, the Yankee pulled the
trigger of his pistol. It failed to fire, and before the man could cock
it again, Will knocked the pistol from his hand.
The Yankee then drew his saber and for a considerable
distance the two fought as they rode, Will attempting to shield himself
from the cuts and thrusts of the Yankee saber. Dodging one of the
Yankee's thrusts, Will raised himself up to tiptoe in the stirrups and
spurred his horse, and with both hands drove the hammer of his gun into
the head of his enemy's fine roan horse, which immediately went down.
Once more, Will Montgomery barely escaped with his life.
Since they seldom wore regular Confederate uniforms,
Will and his fellow scouts were sometimes mistaken for Federals and came
under fire from friend and foe alike. Will had more than one horse shot
out from under him, and often raided for Federal horses. Once, when
trying to capture an ammunition wagon drawn by "six beautiful sorrel
mules," he was shot in the left arm. He mounted the wagon's saddle
mule and, for the first time in his life, drove a six mule team. He
could have brought the wagon safely to Confederate use, but his own men
galloped up and proceeded to kill every mule in the train before he
could stop them. Will grabbed the reins of a passing riderless horse and
In March 1864, Will Montgomery was commissioned a
captain in the Confederate Army and directed to raise his own company of
scouts. Most of the sixty Montgomery Scouts, a mix of the young and old,
had never fought before. Veterans included Will's cousin Ed, first
lieutenant, and his brother Ches and J. M. Selser, who were among the
company's private soldiers.
A typical order dated January 24, 1865, directs
Captain Montgomery to "... move with your company to the vicinity
Natchez and operate vigorously against the enemy in that section until
further orders. You will arrest all deserters
and conscripts... You will
shoot all 'Jayhawkers' and men engaged in outlawing and depredating on
property of the citizenry... “
Will Montgomery's operations in the Natchez area may
have drawn the attention of the writer George Washington Cable; the
young hero of Cable's novel, The Cavalier, bears more than a passing
resemblance to Captain Montgomery.
Eventually, the company joined with General Wirt Adams' Brigade and
fought in Alabama. It surrendered in Gainesville on May 12, 1865, near
the anniversary of the day Will Montgomery first offered his services to
Will's father died shortly after the war, and he undertook the care of
his family and land. Admitted to the bar in 1868, he became a Major in
the state militia in 1875, and served in the Mississippi State Senate in
1878 and the House of Representatives in 1898. That same year, he was
commissioned a Colonel in the United States Army for the
Spanish-American War. He remained vigorous and active, writing his
memoirs and engaging in public life until his death in October, 1925.
Kay Cornelius, published author and historian,
grew up in Tennessee, and has lived in
Huntsville, Alabama, since 1958.
She is the author of eight
historical fiction romances,
historical novella, two contemporary
books for children and young adults and
articles about historical people including
a noted Confederate scout
from Edwards, Mississippi.
Her books can be found on Amazon.com.
Bibliography of Sources Consulted:
Montgomery, William Alexander. Sr.
Fragment of a war
memoir as found in the Manuscripts Division of the Mississippi
Department of Archives and History;
Montgomery, William Alexander, Sr.
Diary, Books One and Two;
(Photocopy of a typed copy furnished to the author by W. H. Montgomery
of Edwards, Ms.,
William Alexander Montgomery’s great-grandson.);
W. A. Montgomery’s Record of the Raymond Fencibles as found in
the Journal of Mississippi History, volume VI;
The Premonition of Death from Champion Hill;
William A. Montgomery, hand-written biographical information
furnished by daughter Olivia Montgomery Champion
Birdsong, and dated
December 20, 1919.