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The Civil War Along Tom's Creek and Waynesboro Pike

Monterey Pass: The Gateway of Agony

John Allen Miller

Be sure to visit the Monterey Pass Battlefield Association's website

Part 4 of 5

During the morning hours of July 4, General Lee's mangled army began it’s withdrawal from Gettysburg. The main portion of the Confederate Army traveled to Fairfield where it would cross over the mountain traveling toward Waynesboro and then onto Hagerstown and Williamsport. There it would meet up with General Imboden who was to lead the wagon train of wounded men through Cashtown.

General Ewell's wagon train was roughly 17 miles long with the contents of "plunder" gathered during the Gettysburg Campaign, as a result of liberal rebel foraging from the farms of Pennsylvania. Five thousand cattle along with a sizable number of free blacks, confiscated as "contraband" of war, were also part of this column.

General Grumble Jones was assigned the task of guarding General Richard Ewell’s wagon train and the mountain passes along with the 6th Virginia Cavalry and 50 men of the 1st Maryland Cavalry under the command of Captain George Emack, whose company took the lead. Assisting Emack was portions of Pogue's and Carter's batteries who were serving as couriers or scouts. Through the driving rain, General Ewell’s wagon train rumbled out of Fairfield traveling toward Jack’s Mountain taking a portion of Iron Springs Road, then through Monterey Pass via Maria Furnace Road.

The head of the wagon column reached Rouzerville late in the evening of Saturday July 4th, where the Confederates took the Old Hagerstown Road going along South Mountain toward Smithsburg. The Confederates learned of the presence of Union forces in that direction and they immediately turned and started for the road that led to Ringgold and Leitersburg.

A turn of the Century view of the Fairfield area from Monterey.

As the daylight gave way to darkness, the mountain proved to be deadly as wagons fell from the cliffs due to the flashes of lightning that almost blinded the horses and their drivers. It started to rain in torrents and the roads became almost impassable as the rain had caused the roads to become badly torn up. At some places flooded streams crossed the road making the conditions worse. The heavy down pours caused many of the fatigued horse and mule teams to stall or drop dead in the middle of the road, creating traffic jams. The Confederate Artillery floundered through the mud as wagons with broken axles were abandoned, along with broken ambulances filled with the wounded.

The town of Waynesboro witnessed the first portion of the Confederate wagon train that was traveling down the mountain side. This large wagon train of wounded soldiers traveled from Fairfield and was conveyed over South Mountain. This must have been a site to see not to mention the noise it brought as hundreds of wagon wheels were rolling through town. In addition to the wounded soldiers it also contained ammunition and supplies of various nature.

General Stuart was given the task of screening the area toward Emmitsburg and Thurmont keeping an eye open for any possible attacks from the Union forces. A portion of Stuart’s Horse Artillery Battalion was to stay behind at Fairfield. Mooreman’s, Chew’s, and a portion of McGregor’s batteries were ordered to protect the wagons of General Ewell’s Corps. Joining them were Robertson’s and Jones’ Cavalry Brigades. As they marched through Fairfield, the artillery was ordered to halt a short distance beyond the Oak Grove Inn.

During the afternoon the artillery sat watching General Ewell’s wagon train moving westward as it traveled the old Iron Springs Road. This road led over Jacks Mountain and Piney Mountain where it cleared the South Mountain range. During the wait Mooreman’s Battery was ordered to move back through Fairfield where it encountered and drove a unit of Federal Cavalry back. Captain W. K. Martin Acting Adjutant of Jones’ Cavalry Brigade noted his regiment was in line of battle, supporting Moorman's battery on the road leading from Fairfield to Emmitsburg. During this small fight Gunner George McDonald was using a newly imported double barrel rifled cannon.

Before darkness, the 2nd Rockbridge Artillery had crossed over Jacks Mountain. There, on top of the mountain they were ordered by General Anderson to leave a section of artillery on top of the Emmitsburg and Waynesboro road. Later that night a portion of the 2nd Rockbridge Artillery was to take position on the hill overlooking Waynesboro, guarding the wagon train as it continued down the mountain. General Anderson was to hold the gaps in the mountains between Fairfield and Waynesboro as he directed his command to Frogtown, located at the base of the mountain.

Courtney's Artillery commanded by Captain William Tanner  was instructed to march to Williamsport with General Imboden's column. Instead Tanner's Battery reached the Emmitsburg Road, south of Gettysburg sometime during the day, while Imboden was preparing to march his wagon train from Cashtown. Therefore, Tanner's Battery marched to Fairfield and then onto Monterey Pass.

After arriving at Monterey, Captain Tanner order one Napoleon cannon to be deployed, while the other four 3-inch rifles continued westward toward Waterloo. Captain Tanner ordered the cannon to be deployed at the eastern slope of Monterey Pass facing the village of Fountain Dale. The men of Tanner's Battery unlimbered the cannon and limber and waited for further orders. The lone cannon had only 5 rounds of ammunition in the limber.

Around 6 p.m. the last of General Ewell’s wagon train had passed by the artillerymen in Fairfield. A cannon from Chew’s Battery was left behind and eventually used to fire upon the Union cavalry as it tried to find a weakness in the rear of General Ewell’s wagon train. The other pieces of Chew’s Battery were to bring up the rear with Cavalry in support, acting as a rearguard for General Ewell’s wagons as they continued over Jacks Mountain.

On the morning of July 4, General Kilpatrick’s Cavalry Division which consisted of General George Custer and Colonel Nathaniel Richmond’s Brigades were ordered from Gettysburg to attack the trains that were moving on the road between Fairfield and Waynesboro. Around 12 p.m. Colonel Huey arrived at Emmitsburg where he met with General Merritt. Colonel Huey then received orders to report to General Kilpatrick who was in pursuit of General Ewell's command, that was reported as being in the mountains in the vicinity of Monterey moving on the road between Fairfield and Waynesboro.

General Kilpatrick’s men rode into Emmitsburg at a full charge, hoping to find parts of the Confederate cavalry in town. They were immediately disappointed. General Kilpatrick reached Emmitsburg at three o'clock in the afternoon. Kilpatrick was then reinforced by Huey's Brigade from General Gregg's Second Calvary Division along with the 2nd U.S. Battery M of the Horse Artillery belonging to Captain John Tidball’s Brigade.

After leaving Emmitsburg with three brigades and a battery, Kilpatrick continued toward the mountains. A short distance from Emmitsburg, the 6th Ohio Regiment of Huey’s command came in contact with rebel pickets who were driven off. Near the hamlet of Fountain Dale, C. H. Buhrman a local farmer learned of the Confederate retreat upon Jacks Mountain. He then mounted his horse and traveled toward Emmitsburg looking for any Federal soldiers in area that he could find. He came across one of General Kilpatrick’s scouts and reported what he had overheard.

When General Kilpatrick learned of the movement of the Confederate cavalry only five miles away at Monterey Pass, he immediately began to pursue the Confederate wagon train. General Kilpatrick traveled about three miles along Waynesboro Pike, when he came across a Confederate scouting party belonging to Captain Emack. Using local citizens as guides, Kilpatrick galloped through the rainy night on a collision course toward the Confederate wagons passing through Monterey. General Kilpatrick came across a local girl, who told him that the Confederates had placed a cannon near the Monterey House on top of the mountain.

At Fountain Dale, the 1st Michigan Cavalry was sent upon a road leading from the right of town to Fairfield Gap, where the enemy was found occupying it. One squadron, under the command of Lieutenant Colonel Stagg against superior numbers made a successful charge. The enemy was driven out and the Gap held until the entire column and train had passed. Here Colonel Stagg sustained heavy losses. In leading the charge, Colonel Stagg’s horse was killed, and Stagg himself was seriously injured by the falling horse. Captain William R. Elliott was also mortally wounded and Lieutenant James S. McElhenny and 17 men were killed. The 1st Michigan retreated back into Fountain Dale and met up with General Custer.

It was about sundown when General Custer’s Brigade was at the base of the mountain. The 5th Michigan was the first of Kilpatrick’s Cavalry Division to climb the mountain. At around 9 pm Custer’s men under the command of General Kilpatrick came in contact with Confederate pickets from Captain George Emack’s company of 1st Maryland Cavalry that were stationed near Fountain Dale, located one mile south of Monterey Pass on the Waynesboro-Emmitsburg Pike.

Hearing reports of General Kilpatrick's movements, Captain Tanner ordered the cannon to be loaded while General Custer's men approached Emack's position. As the weather conditions worsened, the Federal soldiers failed to recognize the Confederate pickets who were wearing black gum blankets over their uniforms. Without making any demonstration, using their bodies to shield the gun, Captain Emack ordered the cannon to fire. The first shot was fired directly into the head of the 5th Michigan Cavalry, causing confusion and chaos in the ranks of the cavalrymen. Two more shots were fired by Captain Tanner's men. After the confusion subsided, Emack's small squad charged and drove the Federals down the mountainside, where Kilpatrick's Artillery was stationed.

Allowing things to calm down a bit, General Kilpatrick and General Custer reorganized before advancing back into the mountain gap. This gave Captain Emack time to concentrate his force at the mountain pass. Orders came to have the cannon to redeploy 100 yards from it's current position and reinforce Captain Emack near the Monterey House where his troopers were deployed on both sides of the road.

Meanwhile, Captain Emack had rode back toward the road that the wagons were on trying desperately to get them moving as fast as they could, while struggling to get the other half of the wagon train that was approaching the pass to stop. Emack later recalled:

"In the mean time the wagons had commenced to run in on the road in my rear, and I again went back on the Gettysburg road and stopped them. They were soon started again, and on going back to ascertain the cause I was informed that they were moving by General W. E. Jones' orders. I found General Jones and told him that I had only a handful of men opposed to all of Kilpatrick's cavalry; and I urged the importance of keeping the road clear, so that when the enemy broke through he would find nothing on it. The general said that the train must move on, and if I could hold out a little longer the 6th Virginia Cavalry would come to my assistance. I returned to my men and urged them not to yield an inch nor to waste any ammunition (we had but little at the commencement)."

In General William E. Jones official report, he stated:

"The evening of July 4th, when it was reported the enemy were advancing in force on the Emmitsburg and Waynesboro' Road, I saw that General Ewell's train was in danger, and asked to go with my command to its protection. I was allowed the 6th and 7th regiments and Chew's battery; but the 7th was afterwards ordered back, and Colonel Ferebee's regiment (4th North Carolina Cavalry) allowed taking its place, the latter being then on this road. This narrow and difficult way, rendered doubly so by heavy rain just fallen, was so blocked by wagons as to render it wholly impracticable to push ahead the artillery or even the cavalry. With my staff I hastened on to rally all the stragglers of the train to the support of whatever force might be guarding the road. Arriving, I found Captain G. M. Emack's company of the Maryland Cavalry, with one gun, opposed to a whole division of Federal cavalry, with a full battery. He had already been driven back within a few hundred yards of the junction of the roads. Not half of the long train had passed. This brave little band of heroes was encouraged with the hope of speedy reinforcements, reminded of the importance of their trust, and exhorted to fight to the bitter end rather than yield. All my couriers and all others with firearms were ordered to the front, directed to lie on the ground and be sparing of their ammunition. The last charge of grape was expended and the piece sent to the rear. For more than two hours less than fifty men kept many thousands in check, and the wagons continued to pass long after the balls were whistling in their midst."

It was during this time that the 6th Michigan Cavalry regiment was ordered to deploy as skirmishers on both sides of the road during the attack on Monterey Pass. For the next several hours in the rain and darkness, the opposing forces engaged in some of the most confusing fighting of the Civil War. In some instances, the soldiers could only tell where the enemy was by flashes of the muzzle from their guns, the cannons or lightning in the sky that illuminated their positions. During the 6th Michigan’s line of battle, Sergeant Elliot Norton was surprised by a rebel officer who leaped from behind a tree and fired his revolver. Sergeant Norton’s life was spared as the bullet traveled through his hat. He then fired at the Confederate soldier killing him instantly.

The 5th Michigan Cavalry was ordered to dismount, leaving the 1st and the 7th Michigan in reserve to charge the Confederate Battery. Custer was also supported by Battery M, 2nd U.S. Artillery and the 6th Ohio Cavalry until they were ordered to Emmitsburg. While Custer was rallying his men, a bullet struck his horse. It was at this time that the 1st West Virginia Cavalry was ordered to charge the Confederate cannon, which it did with all the strength they could muster.

At the Monterey House, General Kilpatrick deployed his Artillery and shelled the Confederate wagons. By 3:00 A.M., along a creek just west of the Monterey House, Custer’s men, supported by Artillery, dismounted and attacked Captain Emack who was reinforced by General Jones near the Tollgate house. Fighting then raged in the woods near the modern day intersection of Route 16 and Charmain Road.

Captain Emack was finally reinforced by the 6th Virginia Cavalry and the 4th North Carolina Cavalry as Custer's men approached the actual pass. During the thickest of the fight, General Jones ordered his couriers and staff officers to get into the fight. The wounded who could fire a gun was also ordered to stand and fight.

Seeing Capehart's Cavalry in their front, Captain Tanner ordered the cannon to fire it's last two shots before the gun was flanked from both sides. Captain Tanner and his crew retreated through the mountain pass and proceeded down the mountainside until they came to Waterloo. One of Captain Tanner's men, Private Thomas Haskins was taken prisoner during the Federal flanking movement on the cannon.

A turn of the Century view of Monterey. This is where the 2nd attack took place. The old Monterey House stood to the right.

As mayhem ensued, both forces fought, leaving Captain Emack wounded by shell, shot, and a saber. Captain Emack and General Jones had to fall back leaving Custer’s men to clear the pass and the 1st West Virginia Cavalry under the command of Major Charles E. Capehart  charged down the other half of the mountain where it found parts of General Ewell’s wagon train. Riding behind the Richmond’s Brigade was General Custer’s Brigade of Michigan Cavalry.

Custer and his troopers finally caught up to the wagon train and immediately began capturing wagons and prisoners, storming through the long line of wagons, collecting their bounty until dawn. Kilpatrick’s Cavalry succeeded in capturing and destroying a large number of wagons, and took 1,360 Confederate soldiers as prisoners. By the morning of July 5th, General Kilpatrick abandoned the fight at Monterey Pass as Confederate reinforcements arrived.

During the battle of Monterey Pass one of the wagon drivers of the Richmond Howitzers was captured by the enemy. Sam Liggon, who was an unarmed wagoneer of the Richmond Howitzers was confronted by a cavalryman who had his saber drawn and demanded his surrender. Sam asked him what unit he belonged to and the reply was the First Virginia. Sam, thinking it was part of his own command then asked him what was the matter and why was he pointing a saber at him. The cavalryman then replied he was from the 1st Virginia of the United States Army. Sam Liggon was forced to yield and stopped the wagon before it was completely surrounded by the 1st (West) Virginia Cavalry.

Union General Judson Kilpatrick thought he was facing more Confederates at Monterey Pass than the mere handful that held off his three Union brigades. The Confederate 1st Maryland Cavalry, with only one cannon and 20 men, held off 7,000 Union troopers for over five hours. The Confederates created so much confusion among the Union ranks that at one point, Emack recalled "the shouting and firing among the retreating enemy we concluded that they had become panic-stricken and were accidentally fighting among themselves."

Union soldiers wrote about their experiences during the battle of Monterey. Kilpatrick stated that they brushed away a force of Cavalry from their front; probably Robertson's picket, but was afterwards attacked, both in front and rear, on a rugged mountain side, where the road was too narrow even to reverse a gun.

Members of General Custer’s brigade spoke of the circumstances that made this midnight battle even worse. Several soldiers told stories relating that the darkness was so intense that the guns could be of little use, except to make the night terribly hideous. The echoes of which reverberated in the mountain gorges in a most frightful manner. Adding to the horrors, the rain fell in floods soon accompanied by the groaning of thunder, while lightning flashed from cloud to cloud, only to leave friend and foe enveloped in the greater darkness.

The mountain elevation was so high that troops on both sides could see the stars and hear the roar of the rain and thunder, as lightning flashed below them. Captain Henry Kidd of Custer’s brigade stated "It seemed as if the infringement were an immense tank. The contents of which were spilled all at once, such a drenching we had! Even heavy gum coats and horsehide boots were hardly proof against it." Captain Kidd continues "It poured and poured, making of every rivulet a river and of every river and mountain stream a raging flood. Many rebels gave themselves up, being heartily tired of this useless war."

General Bradley T. Johnson, commanding the Maryland Line later wrote about the battle of Monterey;

"Meade detached Kilpatrick’s division down through Maryland to strike Lee’s trains in the mountains, and at midnight it attacked them at Monterey, on the dividing line between Maryland and Pennsylvania—Mason and Dixon’s line. Emack’s and Welsh’s squadrons were at the point of attack. They were thrown behind the stone fences, part held mounted, and as Kilpatrick’s advance charged in the pitch dark, the Marylanders sent them whirling back, and charged them mounted. These two squadrons held back Kilpatrick’s division from midnight until dawn, when Jenkins got up, it having been impossible to pass the wagon train in the dark. They saved Ewell’s train, his ammunition and his ambulances with his wounded."

The action of Monterey Pass was so intense that the citizens of the town of Waynesboro had not yet been sure of the result of the battle of Gettysburg. When they saw the fires extending from the top of the mountain all the way down to Leitersburg, great excitement prevailed that night. The ammunition wagons were set on fire, they beheld fireworks and they heard explosions of which no Independence Day celebration has given them before or since.

As the battle of Monterey was just beginning Chew’s Battery was moving from Fairfield. Private Charles McVicar of Chew’s Battery mentioned that heavy rain made traveling impossible crossing through the mountain gap near Monterey. He could hear the roar of cannon fire in the distance about 2 1/2 half miles away. He also noted that the sharpshooters were very hard at work. The firing was very rapid as daylight was nearing. The road was littered with wagons of the dead and wounded from the battle the day before. They managed to find a place for one gun to be unlimbered and fired a few shots at Federal soldiers. The Federals fell back afterwards but not before cutting down a few more wagons. The federals took up positions on the heights. Private McVicar noted that his gun was supported by two regiments of infantry and threw up breastworks within an hour. The firing was constant and it was a night of horror that he would never forget.

Gunner Neese of Chew’s Battery explained what happened to his unit during the night while they traveled over the road toward Monterey. Before daybreak on the fifth, the 6th Virginia Cavalry under the command of Captain John A. Throckmorton came running down the mountainside. Captain Chew asked the Captain what was going on and that he had been sent to support him. The Captain replied that his command had been fired on by Union Artillery and that the 6th Virginia would not go back until daylight. Captain Chew was never given the opportunity to support the 6th Virginia as ordered. They went back down the mountain where they waited for daylight.

Located somewhere behind Chew’s Battery, Pegram’s Artillery Battalion of Pender’s Division of Hill’s Corps began its march back to Virginia. Drivers of the caissons from this Battalion whipped their teams of horses trying to keep moving so they wouldn’t sink down into the mud. Many horses had to be abandoned along the roadside near Monterey. The wounded men had it worse, their cries were eventually silenced being overshadowed by the thunder that cracked echoing throughout the valley.

John Marye of the Fredericksburg Battery (Part of Pegram’s Artillery Battalion) remembered "Never shall I forget that night’s march." He continued "Their cries and appeals to their comrades to leave them by the roadside or else to shoot them and end their misery, ring in my ears to this day." Many of the enlisted men of Pegram’s Battalion who had been wounded at Gettysburg traveled back to Virginia in ammunition wagons that crossed the mountain at Monterey. Their bodies were jolted with every movement of the wagon which made the pain of their injuries even worse.

General Wright moved from Gettysburg to Fairfield at around dark. Because of the downpour it was midnight before he arrived in Fairfield. The general was handed orders and told to move on to Monterey Gap to support Iverson’s Brigade that was under attack from the Union Cavalry. At dawn, General Wright came upon the rear of the train but found the road completely blocked, making further progress impossible. He halted his men and permitted them to take a rest in the mud, while he went to find Iverson. The latter assured him that the danger was past. Wright directed him to move on toward Waynesboro while he held the pass.

General Wright later recalled:

"About daylight, I came upon the rear of the train upon the top of the mountain, but found the road so completely blocked up as to prevent my farther progress. I halted my command, and permitted the men to lie down and take a little rest, while I rode to the front, to ascertain the exact condition of affairs. I found General Iverson near Monterey, and not far from the Waynesborough turnpike, and from his learned that all the danger to the train had passed, and I directed him to move on in the direction of Waynesborough as rapidly as possible, so as to enable our troops to get through the mountain pass."

After the battle of Monterey Pass, General Kilpatrick’s Cavalry continued down the mountainside to Waterloo, present day Rouzerville. There he continued to destroy wagons and capture more Confederate soldiers. The First Rockbridge Artillery had their supply wagons destroyed by Kilpatrick’s Cavalry in an engagement at Waterloo. In these wagons were utensils, cooking supplies, food, baggage belonging to their officers, and about 25 men who were sick, wounded, or dying.

The Powhatan and Salem Artillery had also suffered a great loss at Waterloo. Because of the lack of ammunition for their cannon, the Salem and Powhatan Artillery was forced to keep marching, trying to avoid capture by General Custer's Brigade. Captain Griffin reported that all of his company's belongings including tents, forages, ovens, books and papers had all been captured or destroyed. Because of this he wasn't able to make a quarterly return for the quarter for all of his losses.

The Fluvanna Artillery’s wagons were also among those destroyed at Waterloo early on the morning of the 5th. Twenty-five of their wagoneers were also captured. The Fluvanna Artillery had begun their march to Virginia on the morning of the sixth. Their wagons were sent ahead with General Ewell’s wagon train. Sergeant Pettit describes the scene in Waterloo; "The wrecks of our wagons captured yesterday, were scattered from the top to the foot of the mountain. About 50 were captured some carried off, others destroyed." Many of the men’s spare clothing, personal possessions, and supplies were in those wagons that were destroyed.

Second and Third Companies of the Richmond Howitzers belonging to Captain Willis Dances Artillery Battalion, Rhode’s Division of General Ewell Corps began their march toward Virginia around 2 a. m. on July 5th. 2nd Company Richmond Howitzers entered Fairfield, as an enemy force emerged in the rear of the column, but they were driven off. Meanwhile, 3rd Company had only gone two miles and by daylight the rain had stopped. The men were cold and their uniforms were drenched. 3rd Company managed to get a hold of some whiskey to keep warm that belonged to 2nd Company. The news of the battle of Monterey Pass must have been one of sorrow as their wagons, ambulances, supplies, and many of their sick and wounded had been captured the day before. Some of their comrades were never seen or heard of again.

As the 1st Richmond Howitzers, belonging to Colonel Henry Cabell’s Artillery Battalion, Mclaw’s Division of Longstreet Corps began it’s withdraw from the blood soaked fields of Gettysburg, they saw first hand the damaged afflicted by the Federal Cavalry under General Kilpatrick during the battle of Monterey Pass. 1st Company had encamped at Monterey Pass on the night of July 5th, during the rainstorm because road conditions made traveling impossible. Colonel H. C. Cabell, commanding his Confederate Artillery Battalion wrote: "During the night of the 4th, we withdrew from our position, and, after a most distressing march, encamped at Monterey Springs the night of the 5th."

After the affair of Waterloo, General Kilpatrick traveled to Ringgold where he ordered his division to halt. The casualties of these battles proved to be devastating for the Confederates. General Kilpatrick stated his losses at Monterey Pass was 1 killed, 12 wounded, and 30 captured. The Confederate official reports state that the Confederates lost more than one thousand men, captured at the battle of Monterey Pass along the Waynesboro and Emmitsburg Road.

Today a historical marker is situated where the wagon train was captured. It reads: "Brown Springs. During Lee’s Retreat. General Judson Kilpatrick U.S.A. took 1500 prisoners and 9 miles wagon train near here."

Today the original roads are still intact, but are on private property. It has been rumored that Confederate soldiers are still buried under modern day Route 16 near the intersection of Old Waynesboro Pike in Monterey. Stories of buried cannon seem to capture our imagination. One story that comes to mind tells of how the Confederates hid a cannon in an old cave off of the original road on what is now called Pennersville Road. Another story states that a cannon was thrown down a well. Yet there is another story about a cannon being buried in a field somewhere near Monterey Lane. The only piece of evidence I have is by Major M. W. Henry who wrote in his official report: "On July 5th we were still marching, at 2 p.m. we took up camp on the South Mountain (near Monterey). The 6-pounder and 12-pounder howitzers, having merely the gun-carriage attached, were abandoned necessarily for the want of the proper means of transportation." The Battle of Monterey is one of the great forgotten battles of the Civil War, let us not abandon the history of this great battle as this cannon is rumored to be.

Read Part 5

Read other civil war articles by John Miller

Be sure to visit the Monterey Pass Battlefield Association's website

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