Custer and the Battle of Waynesboro
by William R. Betson
No American military figure is more controversial than George Armstrong Custer.
A general and national hero in his twenties, his fabled death at the Battle of
the Little Big Horn only increased his legendary status among his countrymen.
But history can be fickle, and history lately has not treated the "boy general"
well. His reputation has changed from grand, courageous hero to despised war
criminal. Indeed, for many his persona now embodies the sins of United States
policy toward Native Americans. Hollywood's portrayal of Custer is quite
revealing. In the 1930's he was the gallant hero portrayed by Errol Flynn in
"They Died with Their Boots On." But by the 1960's he was the despicable,
racist, idiot of "Little Big Man."
But what kind of soldier was this American icon? To many he was a reckless fool
who was only lucky that he did not meet his end during the Civil War. To others
he was a brilliant cavalry leader who was central to Union victory at
Appomattox. Interestingly, his reputation among his peers was also divided.
George Crook thought him a humbug; while Philip Sheridan loved him.
Any considered judgment of Custer's military abilities, however, should include
an analysis of his performance in a relatively small action on March 2, 1865 at
Waynesboro, Virginia. In this battle the 25 year old Brevet Major General
Custer demonstrated the bravery and initiative that had made him famous. In a
brilliant action he attacked and completely destroyed the last remaining
organized Confederate force in the Shenandoah Valley. This article will
chronicle that fight - what might have been Custer's greatest day as a soldier.
Custer's rise in the Union Army during the Civil War can only be described as
meteoric. After graduating last in the West Point Class of 1861 he quickly
gained the attention of senior Union officers for his bravery and energy in
combat. McClellan plucked him from the 5th U.S. Cavalry Regiment to serve on
his staff. With this high-level visibility Custer soon became a favorite of
Alfred Pleasonton, the Commander of the Cavalry of the Army of the Potomac. In
July of 1863, trying to inject more energy into the cavalry, Pleasonton
promoted three of the brightest staff officers, Captains Wesley Merritt (age
29), Elon Farnsworth (age 27), and George Custer (age 24), to Brevet Brigadier
General. Along with this promotion came command of cavalry brigades. Thus, at
an age when today's Army officers are being promoted to 1st Lieutenant, George
Armstrong Custer became a general.
The young officer immediately made his mark. He fought and won a small action
on his first day in command. A few days later he and his "Wolverines" (the
brigade's regiments were all from Michigan) fought a successful action against
Jeb Stewart near Gettysburg, protecting the Union flank during that decisive
battle. In these initial actions Custer had demonstrated guts and
determination, but it initially was his personality that initially made him
He exhibited a flair for the dramatic in addition to real leadership ability.
He ostentatiously wore an outlandish uniform and long blonde hair down to his
shoulders - an affectation that endeared him to his men, but caused some
grumbling among his peers and superiors. But he was more than mere show. He was
almost recklessly brave and always led from the front. This earned him
everyone's respect. One would think that his subordinate officers would resent
the fact that a boy was promoted over their heads, but they quickly became
loyal as well. Soon the Michigan Brigade became the most celebrated of the
Union Cavalry formations.
And they earned their celebrity. In 1864 at Newby's Station, Todd's Tavern, and
during Sheridan's Richmond Raid, the Michigan Brigade and Custer distinguished
themselves. At the Battle of Trevilian Station Custer routed the Confederates
with a bold charge. Another of his bold, mounted charges at the important
Battle of Yellow Tavern was crucial to the major victory won that day by the
Union Cavalry over the Confederate Cavalry. In fact, it was just after this
charge that one of Custer's men shot and mortally wounded the fabled
Confederate Cavalry leader Jeb Stuart. And after most of the Army of the
Potomac's Cavalry was transferred with their new commander, General Philip
Sheridan, to the Shenandoah Valley, Custer played a pivotal role in the Federal
victory at the Battle of The Opequon (3d Winchester), as his brigade was one
that helped envelop the Confederate left.
Thus, there was little surprise when in late September, 1864, Custer was
promoted to command the 3d Cavalry Division of Sheridan's Army of the
Shenandoah. His first test as a division commander came quickly. In a
brilliantly conducted maneuver on 19 October 1864 the Confederate Jubal Early
attacked and surprised the Union Army of the Shenandoah near Cedar Creek,
Virginia. The Rebels quickly routed two of the three Union infantry corps, but
the third Union corps (the VI) and the Cavalry Corps refused to be stampeded.
They eventually succeeded in bringing the Confederate advance to a halt, and
Custer's Division was prominent in stabilizing the Union defense. It checked a
Confederate cavalry thrust to the Union rear and fought defensively first on
one flank and then the other. Philip Sheridan, who had been away from the Army
at the time of the attack, famously galloped his charger back to the
battlefield, rallied his troops, and organized a counterattack. Custer's
Division formed the right flank of the Union formation and broke the line of
the elite Rebel division of John B. Gordon. Custer's troopers then spearheaded
an exploitation that completely routed Early's force.
The Battle at Cedar Creek was decisive, for it not only ended any Confederate
hopes of launching any future offensives out of the Shenandoah Valley, it
eliminated any Rebel hopes that they could even seriously defend it.
Recognizing this fact, Robert E. Lee recalled four of Early's five infantry
divisions and all but a small remnant of his cavalry back to the defenses of
Richmond and Petersburg. This left Early with only the infantry division of
Gabriel C. Wharton, with which he could do little more than observe the valley
from one of its southern exits.
The division left with Early was a veteran one. Not a traditional part of the
Army of Northern Virginia, it had spent most of the war campaigning in West
Virginia. Early in the war some of its veterans had even fought at and escaped
the Confederate debacle at Fort Donelson. It had on occasion come east to fight
in the Valley, and once even in the Richmond vicinity at the time of Cold
Harbor. Perhaps its proudest moment was at the Battle of New Market, when,
having taken under its command the Virginia Military Institute Cadet Battalion,
it launched the attack that won the battle. Interestingly, one of it's brigade
commanders - until mortally wounded at Winchester - was Colonel George S.
Patton, grandfather of the World War II general. By February of 1865, however,
this division was a shadow of its former self. One of its brigades had been
detached back to West Virginia, and the division's two remaining brigades could
field less than 1500 infantrymen. Nevertheless, small veteran Confederate
divisions such as this one had shown to be tough in many battles during the
last year of the war. This was not a force to be taken too lightly.
As for Sheridan's Army, their strategic objective in the Shenandoah having been
achieved after Cedar Creek, the issue was now what its role was to be as the
spring campaigning season began. But Ulysses Grant and Sheridan did not agree
as to what that role should be. Grant, ever the operational/strategic thinker,
wanted Sheridan to drive south and cut the Confederate rail line at Danville,
VA, near the North Carolina border, and join Sherman's forces moving north. The
Danville Railroad (made famous by the song "The Night They Drove Old Dixie
Down") was literally the lifeline of the Rebel army defending Richmond and
Petersburg, and cutting it might force Lee to give up his positions near
Richmond and end the deadlocked trench warfare around that city. Sheridan,
however, wanted no part of a move to Danville, and had been dragging his feet
and resisting such orders all winter. Perhaps he believed that his force would
be too isolated from the rest of the Union forces and vulnerable to a sudden
move south by Lee. Or perhaps he did not want to miss being in for the kill
when Lee and the his Army were finally overrun in Virginia. At any rate, when
on 27 February 1865 Sheridan's Army of the Shenandoah left its winter
encampment and marched south, its orders were to proceed to Lynchburg, destroy
the railroads and canals in the vicinity, and be in position to continue the
move further south. He would not carry out those orders.
For the Spring campaign Custer's command had been reinforced from two to three
brigades. The 1st Brigade, Commanded by COL Alexander Pennington, consisted of
the 1st Connecticut, 3d New Jersey, 2d New York, and the 2d Ohio Cavalry
Regiments, and a battalion of the 18th Pennsylvania. The 2d, commanded by COL
William Wells (acting for John Coppington) had the 8th, 15th, and 22d New York
regiments, along with a squadron of the 3d Indiana, and a detachment of the 1st
New Hampshire. The new 3d Brigade, commanded by COL Henry Capehart, had the 1st
New York (known as the "Lincoln" Cavalry), the 3d West Virginia, and elements
of the 1st and 2d West Virginia. Custer's Division counted some 4,500 troopers
at full strength. All sporting distinctive red ties to mark them as a member of
Custer's Division, they were a proud bunch.
Their march south was miserable - only a soldier can know how miserable. It was
raining mixed with sleet most of the time, the roads were in horrible
condition, and the streams and rivers were swollen. On the second day, while
swimming the North Fork of the Shenandoah in freezing weather, one soldier from
the 1st Brigade drowned. But despite the hardships, by all accounts the morale
of Custer's men was sky high. They were well mounted, magnificently equipped,
and confident they could whip anybody in their way. They would quickly
demonstrate that their confidence was well placed.
Having crossed the North Fork of the Shenandoah River on the 28th, the next day
Custer's men approached the Middle Fork near Mount Crawford and ran into the
Rebels. There waited Confederate General Thomas Rosser, one of the pantheon of
southern cavalry heroes. But Tom Rosser was also George Custer's best friend.
Very close while at the academy, the two had already met many times on the
battlefield, lately with the results going all George Custer's way. But on this
day Rosser had perhaps 300 men, and could not stop the Union mounted force. He
could, however, delay the Yankees by burning the long wooden bridge over the
river. This he tried to do.
Map of Battle of Waynesboro
But Custer's men had other ideas. In an aggressive move that characterized
Custer's command, Henry Capehart had two of his regiments swim the river to
strike at the Rebel flank. Once they got across Capehart led the rest of his
brigade in a mounted charge across the bridge. They scattered Rosser's men to
the winds, put out the fire, and chased the fleeing Confederates to Staunton,
which Sheridan's entire force occupied later in the day. This action would be a
harbinger of things to come. Meanwhile Early had withdrawn the remaining
Confederate force east from Staunton along the railroad to Richmond, and taken
up a defensive position along a ridge near Waynesboro. He had told the citizens
of Staunton before he left that Waynesboro was where he intended to fight.
Sheridan had now reached a decision point. He could follow his orders and
continue south to Lynchburg to meet Sherman, or turn east and face Early.
Claiming (rather unconvincingly) that he could not leave Early behind him to
continue to threaten the valley, Sheridan turned east and headed toward
Waynesboro - and eventually Richmond. He directed Custer to take the lead and
move out on March 2d to "ascertain something definite in regard to the
position, movements, and strength of the enemy, and, if possible, to destroy
the railroad bridge over the South River." Custer would do more than that.
Although the Virginia Central Railroad headed east from Staunton through
Waynesboro, no good roads did. As they moved east, Custer's men once again
struggled through horribly muddy roads in a frigid downpour. Custer reported
that by the time his men had traveled a few miles, they were unrecognizably
covered with mud. Despite the weather Custer's men quickly drove in the Rebel
pickets when they reached them some six miles from Staunton. Having driven the
pickets 4-5 miles, Custer then came upon the prepared Confederate position at
At first glance the Confederate position appeared strong. Placed on a hill in
front of the Southern Branch of the Shenandoah River (see map), the fourteen
(some sources say 11) cannon that Early had seemed to dominate all approaches.
Thus, although the position was rather long for the amount of infantry in
Wharton's Division, the guns should have made up for that weakness. Indeed, in
the front near Richmond, this number of troops and guns would have seemed quite
normal. After probing the position with elements of Wells' Brigade, Custer
concluded that a direct frontal attack would result in prohibitive casualties.
Instead he began a careful reconnaissance of the position.
Thus, on this day at least, Custer was not the reckless, impulsive thruster
that some claim. Further, his practiced eye for terrain soon discovered the
weakness in the Confederate position. For although Early had placed his troops
on the enemy side of a concave bend in the river, he had anchored his left not
on the river itself, but on a set of woods south of the hill that dominated the
town of Waynesboro. Custer quickly formulated a plan to exploit this weakness.
The plan would demonstrate that Custer could be a prudent commander and a first
rate, imaginative tactician.
Instructing Wells Brigade to maintain a strong mounted skirmish line to the
enemy's front to keep the Rebel attention, he directed his Chief of Staff,
Lieutenant Colonel Edward Whitaker, to take three regiments of Pennington's
Brigade (2d Ohio, 3d New Jersey, and 1st Connecticut) and infiltrate the woods
in order to take a flanking position on the enemy's right. Importantly, these
regiments were all armed with Spencer repeating rifles. Custer then had his
artillery, 2 guns of the 2d US Artillery under LT Carle Woodruff, conduct a
visible withdrawal to deceive the enemy, but then return through the woods to
take up firing positions, hopefully without being seen . Finally, he massed
Capehart's Brigade behind Wells' and prepared it to make a mounted charge. At a
signal Woodruff's guns would open fire to keep the enemy heads down, Whitaker's
three regiments would charge the Confederate flank on the run firing their
repeaters, and Capehart's mounted force would charge down the road mounted and
The plan worked like a charm. Surprised by the attack on their flank and stung
by the firepower of the repeating rifles and the masked artillery battery, the
proud Confederate victors of New Market and many other battles broke almost
immediately and ran toward the bridge to their rear. The Rebel artillery stuck
to their guns and tried to resist. But they were quickly overrun by the mounted
attack of Capehart's lead unit, the 8th New York Cavalry. One gun was captured
with the ramming sponge still in the tube. Within minutes all organized
Confederate resistance ceased and Wharton's Division dissolved in rout. The
unorganized survivors tried to get to the bridge over the river and apparent
safety, but were ridden down by the aggressive Union cavalry.
Rarely in military history has a victory been so complete. Wharton's Division
was killed or captured (mostly the latter) almost to a man. The 8th New York -
strength about 400 - captured 800 prisoners. Total Rebel prisoners numbered
perhaps 1500 (the exact number is unknown). All of the Rebel guns were taken,
along with nearly 200 wagons - the entire train of the Confederate Valley
District. General Early and his immediate staff somehow escaped, although he
lost his headquarters wagons and all his papers and records. Jubilant Union
troopers also seized 17 Confederate battle flags - and recaptured the flag of
Union General George Crook's Corps, captured at Cedar Creek. For their efforts
that day a grateful Union government awarded Custer's Division a total of 15
Congressional Medals of Honor. The cost to Custer's 3d Cavalry Division for
this stunning triumph in total killed and wounded was a mere 9 soldiers.
Later that day a proud Custer reported to Sheridan's Headquarters followed by
seventeen 3d Division troopers, each carrying a captured battle flag. It was
certainly a heady moment for the 26 year old, and Sheridan described the action
in his official report as a "brilliant fight." But of course the fighting was
not over for Sheridan, Custer or their men. After Waynesboro Sheridan moved
slowly eastward toward the main armies fighting near Richmond, destroying the
railroads and anything of military value along the way. Sheridan and Custer
then played key roles in the decisive Union victory at Five Forks and the
ensuing pursuit of the Lee's Army of Northern Virginia. And, not surprisingly,
it would be Custer's Division that blocked the last Confederate escape route,
precipitating Lee's surrender.
So what are we to conclude from this action about Custer the soldier. . Clearly
he had the ability to see and understand the battlefield at a glance -
something Clausewitz described as a major element of military genius. He also
knew how to achieve synergetic effects through the use of combined arms. On
this day his employment of a combination of mounted and dismounted soldiers,
his exploitation of the firepower of his cannons and his soldiers' repeating
rifles, and his ability to synchronize it all with thunderclap surprise was
Many histories of the Civil War dismiss this action, suggesting that Early was
defeated by Sheridan's overwhelming force. But this is not true. 1500 infantry
and 11 guns in prepared positions should have been able to hold against 4500
cavalry and 2 guns (and only two thirds of Custer's men actually participated
significantly in the fight). Others argue that the Rebels simply had no more
fight in them. Certainly Confederate morale was not at the highest level. But
this Confederate Division was a veteran formation that had fought hard a few
months prior at Cedar Creek. The difference this day was Custer and his ability
to see the battlefield and employ his forces with a tactical virtuosity that
still seems astonishing. This performance certainly puts Custer in a class with
the greatest cavalry tacticians that the United States has produced
Of course, Custer will always be most remembered for the day on the Little Big
Horn when his eye for the battlefield and his tactical instincts failed him.
But that was a different day and a different enemy. Any balanced appraisal of
Custer as a soldier must remember what he did in March, 1865.
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. Washington, DC, Government Printing Office, 1895
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Scott, LTC Robert N., ed. The War of the Rebellion: A Compilation of the
Official Records of the Union and Confederate Armies, Volume 46/1 .
Washington, DC. Government Printing Office, 1880.
Starr, Stephen Z. The Union Cavalry in the Civil War, Volume 2 .
Baton Rouge, LA, Louisiana State University Press, 1981.
Urwin, Gregory, J.W. Custer Victorious: The Civil War Battles of General
George Armstrong Custer . Teaneck, NJ, Fairleigh Dickenson University
Wert, Jeffry D. Custer: The Controversial Life of George Armstrong Custer
. New York, Simon and Schuster, 1996.
Written by William R. Betson
Copyright © 2004 William R. Betson