By: Eric J. Wittenberg

As we will recall, Gregg's Third Division was to cross the Rappahannock River at Kelly's Ford, in conjunction with Buford's attack at dawn, and to drive on the town of Culpeper from the south. As we have seen, the Union plan was badly flawed in that it assumed that there would be little or no Confederate resistance at the respective fords. Instead, both Beverly's Ford and Kelly's Ford were picketed by the Confederates, and Gregg's division got a much later start than expected.

Brig. Gen. David McMurtrie Gregg was 30 years old in June 1863. Originally from western Pennsylvania, he was a first cousin of the governor of Pennsylvania, Andrew Gregg Curtin, a political connection that served Gregg well throughout his career. Gregg graduated from West Point in 1855, and joined the First Dragoons as a brevet second lieutenant. After service in the west, Gregg came east at the outbreak of the Civil War, and was appointed colonel of the 8th Pennsylvania Cavalry in 1862. Serving with distinction in the 1862, campaigns, Gregg was promoted to brigadier general of volunteers in November 1862, and commanded a division under George Stoneman. Gregg was a solid, competent cavalryman, respected by the likes of John Buford, Alfred Pleasonton, and George Stoneman. (1)

For the coming reconnaissance in force, Gregg was given command of the left wing of the Cavalry Corps. His command, consisting of his own Third Division and Col. Alfred N. Duffie's Second Division, was to cross at Kelly's Ford. The two forces were then to split-Gregg's division, supported by Russell's infantry, was to advance on Fleetwood Hill via the Kelly's Mill Road, while Duffie's column was to advance through Stevensburg, and to come in on Culpeper from the south.

Kelly's Ford was picketed by the green brigade of Brig. Gen. Beverly H. Robertson. This brigade, made up of two large but completely inexperienced North Carolina regiments, was picketed in the area immediately surrounding Kelly's Ford. Robertson was also a West Pointer-he graduated in 1849. His entire service in the Regular Army was in the 2nd Dragoons on the western frontier. He had served under Turner Ashby in the Shenandoah Valley, and had assumed command of Ashby's Brigade after the legendary cavalier was killed during Jackson's Valley Campaign. He had done well in that position, besting John Buford in the final engagement at Second Manassas, but had been relieved of command shortly thereafter. Jeb Stuart despised him, and once described Robertson as the "most troublesome man in the Army". (2) Stuart thought that he had rid himself of the troublesome Robertson by banishing him to North Carolina, but his green brigade was called to Culpeper for the forthcoming invasion of the north. Thus, Stuart was again burdened by an officer he despised. This fact would have major consequences for Southern fortunes at Brandy Station.

Gregg's crossing was supposed to coincide with Buford's. However, Duffie's division was late to the rendezvous, and the entire crossing was delayed for several hours. Gregg later wrote that Duffie's delay was "unnecessary", and that it "seriously interfered with the movement." (3) When Gregg's skirmishers finally got across the river, they found Robertson's Brigade there, doing picket duty. Like Buford, Gregg was surprised to find Confederate resistance at the ford; intelligence had failed to disclose the presence of Rebel pickets at the ford. Gregg's men captured Robertson's pickets before they could spread word of the Yankee approach, and Gregg's column splashed across the Rappahannock. When Robertson heard of the advance by the Yankee troopers, he sent word to Stuart of the Yankee advance. Robertson later claimed that Stuart ordered him to fall back from Kelly's Ford to Fleetwood Hill, leaving the road to Brandy Station open for the Yankee advance. (4) Stuart then countermanded the order, and Robertson was directed to take his command back to the Kelly's Mill Road position and to block the Union route of advance.

Robertson obeyed this order, and immediately ran into Union skirmishers. Robertson shortly discovered that Gregg had flanked his position, and that his force was rapidly moving toward Stuart's main position. He did little else to check the Yankee advance which proceeded largely unhindered. Stuart later wrote:

Brigadier-General Robertson kept the enemy in check on the Kelly's ford road but did not conform the movement of the enemy to the right, of which he was cognizant, so as to hold him in check or thwart him by a corresponding move of a portion of his command in the same direction. He was too far off for me to give him orders to do so in time... (5)

Robertson wrote that his reason for failing to act to hinder the Yankee advance was in an effort to check the advance of Russell's infantry, a somewhat lame excuse at best. He further claimed that his small brigade was an insufficient force to hinder the Yankee advance. His small brigade spent the balance of the day jousting with Russell's infantry near Kelly's Ford. It was no factor at all in the great cavalry battle raging just a few miles away. His casualties that day totaled four horses killed. (6)

The fact that Robertson failed to delay the Yankee approach meant that Gregg's approach, slightly longer as a result of the need to flank Robertson's position, was made completely unhindered. It left the Confederate flank open to attack, and left Fleetwood Hill completely uncovered. The march to Fleetwood Hill was a pleasant one for the Federals. Gregg noted, "The country about Brandy Station is open, and on the south side extensive level fields [are] particularly suitable for a cavalry engagement." (7) William Blackford, of Stuart's staff, recorded in his memoirs, "the waste of war had removed the obstacles to cavalry maneuvers...fences and forests; and the ground was open, level and firm." (8) However, Gregg made a crucial error. He could plainly hear Buford's guns roaring at St. James Church, and, instead of marching immediately to the guns over the shortest overland route, he took a longer, more roundabout route, meaning that Stuart could concentrate the fury of his entire command on Buford.

Gregg had two brigades, under command of Col. Sir Percy Wyndham and Col. Judson Kilpatrick. Wyndham's column led Gregg's advance on the left, with Kilpatrick's column just behind and to the right. Some time around 11 a.m. , nearly 7 hours after Buford's initial attack, Wyndham's command crossed over the tracks of the Orange and Alexandria Railroad and headed for Fleetwood Hill. As the dominant feature of the surrounding terrain, if Gregg could capture Fleetwood Hill, his position would dominate the line at St. James Church, and Stuart's force would have to abandon its strong line there, and Stuart's primary route of retreat to Culpeper would be cut off.

Grumble Jones somehow learned of the Yankee advance; perhaps one of Robertson's couriers informed him. Jones sent a courier to Stuart with this information. Stuart snorted when he heard the courier's report, and responded, "Tell Gen. Jones to attend to the Yankees in his front, and I'll watch the flanks." The courier returned to Jones, reported what Stuart had said, and it was Jones' turn to snort. He retorted, "So he thinks they ain't coming, does he? Well, let him alone; he'll damned well soon see for himself." (9) This prediction was proved correct soon enough.

As Gregg's column approached, he could see the fight raging in the distance, the roar of the artillery booming in his ears as he rode to the front. Longing to join the fray, Gregg gave the order for his troopers to draw sabres, and

The word was given-their willing blades leaped from their scabbards, and with one wild, exultant shout they dashed across the field, on, over the railroad, and, with Wyndham at their head, rode over and through the headquarters of Stuart, the rebel chief. (10)

As indicated above, Fleetwood had served as Stuart's headquarters. His tent-fly was still there that morning. It had been picketed by two of Hampton's regiments, the 2nd North Carolina and 4th Virginia, but these two regiments had been sent to Stevensburg to block Duffie's line of march. (See lesson 5 for the specifics of this fight) This meant that, other than a few miscellaneous staff officers and orderlies, the dominant topographical feature of the area lay unprotected. Fortunately, one artillery piece, a six-pounder Napoleon, of Capt. Roger P. Chew's Battery of Horse artillery, and commanded by Lt. John W. Carter, happened to be there. Carter had exhausted his ammunition in the whirling melee at St. James Church, and had pulled back to Fleetwood to refill his limber. Major Henry B. McClellan, Stuart's fine adjutant, was the highest ranking officer in the area.

Maj. McClellan was a transplanted Philadelphian, and a first cousin of George B. McClellan. He was a fine staff officer who found himself in the right place at the right time this day. Just a few minutes after receiving word from one of Robertson's couriers that the Yankees were advancing on his exposed position, the head of Wyndham's column came into view. Seeing the urgency of the situation, McClellan sent a series of orderlies off to warn Stuart of the urgency of the situation, and sprang into action.

McClellan described the scene:

They were pressing steadily toward the railroad station, which must in a few moments be in their possession. How could they be prevented from also occupying the Fleetwood Hill, the key to the whole position? Matters looked serious! But good results can sometimes be accomplished with the smallest means. Lieutenant Carter's howitzer was brought up, and boldly pushed beyond the crest of the hill; a few imperfect shells and some round shot were found in the limber chest; a slow fire was at once opened upon the marching column, and courier after courier was dispatched to General Stuart to inform him of the peril...(11)

The few shots lobbed by Carter's gun caused confusion in the Federal ranks, and they paused a moment to evaluate the threat.

This delay was critical. McClellan pointed out, "in point of fact there was not one man upon the hill beside those belonging to Carter's howitzer and myself, for I had sent away even my last courier, with an urgent appeal for speedy help. Could General Gregg have known the true state of affairs he would, of course, have sent forward a squadron to take possession; but appearances demanded a more serious attack, and while this was being organized three rifled guns were unlimbered, and a fierce cannonade was opened on the hill." (12)

McClellan's couriers found Stuart, directing the fighting at St. James Church. The gray cavalier was skeptical at first, but the repeated urgency of McClellan's messages combined with the sound of cannonading caused Stuart to pull the 12th Virginia Cavalry and the 35th Battalion of Virginia Cavalry, of Jones' Brigade, from the St. James Church line, and to send them to Fleetwood. It took a few, precious minutes for the Confederate reinforcements to reach Fleetwood Hill. As the head of the small Confederate column reached Fleetwood, it met Carter's withdrawing gun, now entirely out of ammunition, and the head of Wyndham's attacking column just fifty yards from the crest of the hill. (13) As Capt. William W. Blackford, of Stuart's staff, recorded, "There now followed a passage of arms filled with romantic interest and splendor to a degree unequaled by anything our war produced." (14)

Stuart ordered the rest of Jones' Brigade, and all of Hampton's Brigade to go to McClellan's aid at Fleetwood, and the Confederate chieftain rode to the sound of the fighting himself, arriving just behind the 12th Virginia. Wyndham's lead regiment, the 1st New Jersey, briefly took possession of the hill, but the Confederate onslaught crashed into him, and the Confederate attack drove the Jerseymen back.

In response, Kilpatrick ordered his brigade to charge, and its charge caused the Confederate force to "break...all to pieces...lost all organization and sought safety in flight." (15) At that moment, all looked bleak for the Rebel cavalry, as Kilpatrick's men struggled up to the crest of the hill. Complete victory was in Gregg's grasp.

At that moment, Hampton's brigade arrived, along with the balance of Jones' force. Personally led by Wade Hampton, the gray cavalry charged head on into the Yankee cavalry at the top of Fleetwood Hill, and the melee was on. Stuart, following along behind Hampton's column, could be heard to yell, "Give them the sabre, boys!" (16) Sabre charge after sabre charge occurred, with the cold steel of the sabres glinting in the afternoon sun. The whirling melee deteriorated into small, isolated fights among pockets of men; all organization was lost on both sides as they clashed on the front of Fleetwood Hill. A member of the 1st Pennsylvania Cavalry remembered, "At one time the dust was so thick we could not tell friend from foe." (17) The regimental historian of the 10th New York Cavalry observed, "The rebel line that swept down on us came in splendid order, and when the two lines were about to close in, they opened a rapid fire upon us. Then followed an indescribable clashing and slashing, banging and yelling...We were now so mixed up with the rebels that every man was fighting desperately to maintain the position the position until assistance could be brought forward." (18)

Maj. C. E. Fluornoy, commander of the 6th Virginia of Jones' Brigade, noted in his official report of the battle that his lone regiment charged into five regiments of Yankee cavalry as it joined the fray. (19) Rallying his troopers, Kilpatrick shouted to the 1st Maine Cavalry, "Men of Maine! You must save the day! Follow me!", and personally led a charge by the Maine troopers. "In one solid mass this splendid regiment circled first to the right, and then moving in a straight line at a run struck the rebel columns in flank. The shock was terrific! Down went the rebels before this wild rush of maddened horses, men, biting sabres, and whistling balls." (20) The charge of the 1st Maine saved the Federal guns which had been put atop Fleetwood Hill from capture.

The Jeff Davis Legion of Hampton's command was placed on the east side of the railroad, while the balance of Jones' Brigade charged on the west side. Their charge drove the Federals back, "and then, for an hour or more, there was a fierce struggle for the hill, which seemed to have been regarded as the key to the entire situation. This point was taken, and retaken once, and perhaps several times; each side would be in possession for a time, and plant its batteries there, when by a successful charge it would pass into the possession of the other side, and so it continued..." (21)

Kilpatrick brought up a battery, J.W. Martin's 6th New York Independent Battery, which deployed in the fields just in front of Fleetwood Hill. From there, Martin's guns annoyed the Confederates greatly, taking a toll on the unsupported Confederate troopers using the crest of Fleetwood Hill as their base of operations. The historian of the 35th Battalion (White's Comanches) noted, "The gallant fellows at the battery hurled a perfect storm of grape upon the Comanches..." (22) Finally growing weary of the annoying Yankee artillery, Lt. Col. Elijah V. White, commanding the 35th Battalion, ordered his men to charge the battery. The unit's historian recorded, "with never a halt or a falter the battalion dashed on, scattering the supports and capturing the battery after a desperate fight, in which the artillerymen fought like heroes, with small arms, long after their guns were silenced. There was no demand for a surrender, nor any offer to do so, until nearly all the men at the battery, with many of their horses, were killed and wounded." (23) White and a few of his men attempted to turn Martin's guns on the Yankees, but White received no support, and a Federal counterattack loomed. Prudently, White pulled back, leaving the guns for the Yankees. Lt. J. Wade Wilson, commanding the Federal battery, noted in his after-action report:

I limbered to the front and sought a position on the crest of the hill behind which the enemy was rapidly massing to force back the advance of Col. Kilpatrick...Before reaching the crest, however, a halt was ordered by Col. Kilpatrick, and, soon after, a retreat from that position, which was executed without panic and in admirable order. The enemy, perceiving the retreat, charged furiously up the hill and through the section fifty yards in rear of the pieces, charging desperately on the cavalry, some hundreds of yards in advance of the pieces in the retreat. The capture of the section seems to have thought accomplished by the enemy, and the rebel line wheeled into column and pushed rapidly by the flanks, with the intent to turn the right of the 1st brigade, leaving, as they supposed, a sufficient force to secure the guns. At this time was displayed the heroism of the section, and valor of which any command and country may be justly proud. In reversing, one of the gun limbers was nearly capsized, one wheel being in the air and the axle nearly vertical. Perceiving this, I ordered the cannoneers to dismount and restore to its position the limber. We were surrounded by a squad of rebel cavalry, firing with carbine and pistol. The order was scarcely needed, for the cannoneers had seen the peril of their gun, and, anticipating the order, had dismounted to restore it; and with revolvers in hand, they defended the gun as if determined to share its destiny and make its fate their own. The bearer of a rebel battle-flag was shot by Private Currant, who would have recovered it but for the great difficulty of approaching the color with a lame and skittish horse upon which he was at the time mounted. The flag was taken by the 1st Maine Cavalry. (24)

The gun was ultimately saved by the courage of the Yankee gunners.

A number of pieces of Beckham's horse artillery were assembled atop Fleetwood Hill as the fight raged unabated. Capt. James F. Hart's South Carolina battery came to Fleetwood with Hampton's brigade. As Hart's guns came up, a bold charge by the Cobb Georgia Legion, supported by Col. John Black's 1st South Carolina Cavalry, cleared the area for the deployment of the Confederate guns. Colonel P.M.B. Young, commander of the Georgians, noted in his report, "I immediately ordered the charge in close column of squadrons, and I swept the hill clear of the enemy, he being scattered and entirely routed. I do claim that this was the turning point of the day in this portion of the field, for in less than a minute's time, [a Federal] battery would have been on the hill." (25) McClellan called this movement "one of the finest which was executed on this day so full of brave deeds." (26)

This charge cleared the way for Hart's guns. Parts of McGregor's and Chew's Batteries joined Hart, and they deployed. Part of the 1st New Jersey Cavalry still occupied a spur of Fleetwood Hill, and, pressed by Jones' cavalry, had no route of retreat available to them, other than to cut their way through the Confederate guns in a scene reminiscent of the fight of the 6th Pennsylvania and 6th U.S. at St. James Church. Capt. Hart described the fight:

Scarcely had out artillery opened on the retreating enemy from this new position than a part of the 1st New Jersey Cavalry, which formed the extreme Federal left, came thundering down the narrow ridge, striking McGregor's and Hart's unsupported batteries in the flank, and riding through between guns and caissons from right to left, but met by a determined hand to hand contest from the cannoneers with pistols, sponge staffs, and whatever else came handy to fight with. Lieutenant-Colonel Broderick, commanding the regiment, was killed in this charge, as also the second in command, Major J.H. Shelmire, who fell from a pistol ball, while gallantly attempting to cut his way through these batteries. The charge was repulsed by the artillerists alone, not a solitary friendly trooper being within reach of us. (27)

With that, the final Federal troopers were driven from Fleetwood Hill by the determined Confederates.

The regimental historian of the 1st New Jersey Cavalry pointed out that "men and horses had been fighting for over three hours and were now utterly exhausted....there were not a dozen horses that could charge-not a man who could shout above a whisper." The Jerseymen had gone into battle with 280 officers and enlisted men, and, in a span of three hours, had lost 56, including its regimental commander and his second in command. (28) The butcher's bill for Gregg's delays was coming due in the afternoon sunlight.

McClellan noted, "Thus ended the attack of Gregg's division upon the Fleetwood Hill. Modern warfare cannot furnish an instance of a field more closely, more valiantly contested. General Gregg retired from the field defeated, but defiant and unwilling to acknowledge a defeat." (29) Instead, Gregg pulled back and reformed his command in the fields to the south of Brand Station, where his initial attacks had staged. He later noted in his after-action report of the battle, "The contest was too unequal to be longer continued. The Second Division had not come up; there was no support at hand, and the enemy's numbers were three times my own. I ordered the withdrawal of my brigades. In good order they left the field, the enemy choosing not to follow." (30)

By this time, Duffie's tardy division had finally reached the field. As the last of Gregg's men pulled back from the southern end of Fleetwood, Duffie's columns came on the field. In the interim, Buford had shifted his forces around Rooney Lee's flank, and was preparing for his grand attack on the northern end of Fleetwood Hill. However, before that attack could begin, Gregg was repulsed at Fleetwood Hill, and Buford commenced another unsupported attack. Finally reinforced by Duffie, Gregg pulled back about a mile and realigned his position to connect with Buford's northern attack, now raging on the far northern end of Fleetwood Hill. Most of the Confederate artillery was placed on Fleetwood Hill, and Hampton's and Jones' Brigades were shifted to meet the Union threat, as Buford's attack swirled on the northern end of the hill. (31) As Gregg prepared to pitch into the fight once again, orders arrived from Pleasonton to disengage and withdraw, and Gregg's command formed up and marched off unmolested, again leaving Buford to go it alone against the Confederates.

As the fight for Fleetwood Hill raged, Capt. William Blackford, of Stuart's staff, had been sent to find Robert E. Lee at Culpeper, to report that Union infantry was involved in the fight. Blackford rode off to find Lee, who personally rode to the battlefield and watched the closing engagements of the afternoon. (32) Watching the sabre fight raging in front of him, Lee was heard to compliment both sides for their bravery and execution. (33) Lee had brought Robert Rodes' infantry division with him, but the Rebel infantry stayed out of the line of sight, so as not to give away their presence in the area.

Gregg's retreat was covered by Russell's infantry, which had spent the entire day keeping Robertson's demi-brigade occupied, and preventing it from being a factor in the fighting at Brandy Station. By the time that Robertson's men finally reached Brandy Station, the fighting was already over. The unpopular Virginian's command, for reasons that remain unclear to this day, had been no factor at all in the fighting. Stuart noted that Buford's attack on the northern end of Fleetwood Hill "made it absolutely necessary to desist from our pursuit of the force retreating toward Kelly's particularly as the infantry known to be on that road would very soon have terminated the pursuit. (34)

The fighting ended. It was a will-o-the-wisp of lost opportunities for David Gregg, a veritably litany of "what if"'s. His command had suffered severe casualties. Two regimental commanders were wounded or missing (including Percy Wyndham), a third field-grade officer wounded, 2 line officers killed and 15 wounded, 18 enlisted men killed, 65 wounded, and 272 missing. His men had captured 8 commissioned officers and 2 colors. Gregg noted, "The field on which we fought bore evidence of the severe loss of the enemy." Gregg singled out Wyndham and Kilpatrick for particular praise, as well as Capt. Martin for the fight put up by his battery. At the same time, he squarely and unambiguously placed blame for his failure to carry Fleetwood Hill on Duffie, both for delaying his crossing, and for his tardiness in arriving on the battlefield. (35)

For his part, Stuart described the fight for Fleetwood Hill "long and spirited." He generally praised all of his brigade commanders, singling out Jones and Hampton for particular praise. At the same time, he damned Robertson for failing to delay Gregg's advance. Finally, he gave particular praise to Henry McClellan, for without the enterprising major's help, Fleetwod certainly would have fallen and the outcome of the battle would have been very different indeed. Stuart admitted to 485 casualties in the day's fighting. (36)

In return, Robert E. Lee praised Stuart. On June 16, after reading Stuart's report, Lee wrote, "The dispositions made by you to meet the strong attack of the enemy appear to have been judicious and well planned. The troops were well and skillfully managed, and, with few exceptions, conducted themselves with marked gallantry. The result of the action calls for our grateful thanks to Almighty God, and is honorable alike to the officers and men engaged." (37) Lee evidently did not realize just how close his cavalry corps came to being completely destroyed that day; if he did, he did a good job of salving Stuart's bruised pride.

Thus, Gregg's fight ended with disappointing results. Had the fortunes of war smiled upon David Gregg that day, the outcome of the battle would have been very different indeed. But they did not, and the gallant Pennsylvania horse soldier was left with nothing but frustration for his efforts.