The Mammoth Book of Prison Breaks (65 page)

Once it was able to accommodate the two men, they slid their way down the rope to Rat Hell, and began to dig the proper tunnel, in what remained of the kitchen area in the south-east corner of the room. Rose was the tunneller, with Hamilton fanning air down into the hole, as well as dragging out the dirt, and concealing it in the rats’ straw. However, they quickly realized that they would not be able to succeed on their own, and made a careful choice of thirteen other men to assist. To help get in and out of the cellar, they created a proper rope ladder with wooden rungs that could be pulled back up and concealed – with some difficulty – after each night’s work.

The men worked in shifts, one night on duty, two off. They initially planned to dig down alongside the east wall, go beneath it, and then turn south, and head for the large street sewer next to the canal that Rose had previously seen workmen entering. From these observations, Rose had guessed that the sewer should be six feet high, and they should hopefully be able to get to the canal without a problem.

That’s when they hit the next snag. Although Rose encouraged them to use their very basic tools to cut through the large timbers that had been used to support the prison on the south side, when they got through these, they realized that they had gone beneath the level of the canal. The danger of this was brought home to them when water began to seep in – slowly, at first, but then suddenly it broke through the tunnel roof, nearly drowning Rose. That branch of the tunnel was quickly blocked up.

The next attempt similarly caused a cave-in, with equally potentially hazardous results. Tunnelling towards a small sewer led to a breach in the pavement outside the prison wall, and the Yankee officers saw their captors looking at it suspiciously. However, when the word “rats” was repeatedly heard, Rose was relieved, although he deliberately took the next duty shift on his own, in case they had been rumbled; if that happened, he would be the only one held accountable. No one arrived to arrest him, so the work continued.

Another sewer was tried, but this was too small for a man to get into unless they removed the wooden planks. This the team did, although by now they were becoming very disenchanted with their lack of progress. By 25 January 1864, they believed, however, that they were about to break through to the main sewer, and everyone bar the two men on duty anxiously waited for the diggers’ return the next morning. To the consternation of their colleagues, the pair reported that the final barrier to the main sewer was made of seasoned oak. The tools they had been using were worn out; it was becoming harder to keep any sort of light blazing to work by. They were ready to quit, despite having spent thirty-nine nights working. (They may also have been discouraged by the ease with which First New Jersey Cavalry soldier John Bray had simply walked out of the prison on the morning of Sunday 10 January, disguised in a Confederate Army coat he had bought from a rather dim-witted guard.)

Rose and Hamilton understood their frustration and disbanded the group. That didn’t stop either man, who decided to start a new tunnel, this time in the north-east corner of Rat Hell, going east. This had the advantage that they were digging through clay, and not heading towards water, but the disadvantage that they would have to reach a shed adjoining the vacant lot, which was easily visible to the guards patrolling the south side of the prison. Rose watched the nearest guard’s movements, and realized that they would have a few moments’ grace while his back was turned patrolling westwards. Additionally, unless it was obvious to him that he was looking at escaping prisoners, he was unlikely to challenge anyone in the streets of Richmond.

After three tries to find a suitable place to begin their new tunnel, Rose and Hamilton began work afresh, and were able to persuade some of their former helpers to return. It was hard work getting through the very densely compacted sand that had been placed around the prison walls when the building was erected, but by sheer hard work, they were able to create a tunnel that was two feet wide in diameter, and around two feet high, set about six inches above the level of the cellar floor. Without any tools, they couldn’t be sure that they were keeping the tunnel totally horizontal, but they did their best.

Teams of five carried out the tunnelling, working day and night now: one digging at the clayface, putting the dirt into a spittoon, which was taken by a second man and hidden in the straw; a third man fanned air into the tunnel using one of Hamilton’s inventions: a rubber blanket stretched across a wooden frame; a fourth man deputized for the second and third men when needed, while a fifth man kept a look out, since the Confederate guards were ordered to check every part of the building regularly. If they were about to come through the south door, the lookout would give a warning, and the three men above ground would hide in the straw, nestling alongside the rats, while the digger stayed within the tunnel. The guards weren’t keen on entering Rat Hell, and tended to stay down the south end, far away from the tunnelling work.

Although strict silence was maintained, Rose made sure that each man knew how much their efforts were assisting with the general escape, and it helped that progress was very clear each day. One evening, one of the diggers became overconfident, and started to dig up to the surface, convinced that they had reached their target. Instead, as he very rapidly realized when he glanced around him, he was still in the open lot, and thought he was clearly visible to a guard, if he happened to look in that direction. One of the other members of the team went to get Rose, who hurried down the tunnel to check, but realized that the situation wasn’t as bad as the digger had feared: although anyone exiting there would be clearly seen, the hole itself wasn’t an immediate threat. He stuffed his shirt into the hole, and covered it with dirt. (The mistake did come in handy though – the next day Rose put a shoe through the hole, and when he looked down at the lot from the prison, he saw that the tunnel had slightly deviated from its course, and got the diggers moving slightly to the left.)

Sixteen days of digging later, on Saturday 6 February 1864, it looked as if everything was lost. A party of Confederate soldiers made a detailed inspection of the cellar, although they didn’t spot the tunnel entrance. Captain Johnson was the only tunneller there at the time; he had missed roll call on a number of occasions, claiming he was only “devilling the clerk” (when he was actually digging beneath the surface), but eventually he was forced to remain in Rat Hell twenty-four hours a day since his reappearance would have led to questions no one would want to answer. That night, he briefed Rose on their activities, and it caused general dismay amongst the escape party. Rose knew they were so near to success, and, once again, wasn’t willing to give up so close to their goal.

From that moment on until the tunnel was complete, Rose himself was the digger, working solidly through Sunday 7th and achieving twice as much in one day as the full teams had managed on their own. He slept Sunday night, and then on the Monday morning started up again. At midnight he reached a post, which he guessed marked the far side of the vacant lot, so he began digging upwards. As he broke through the surface, he heard the watch call out 1.30 a.m. He was free.

After taking a few moments to breathe in the fresh air, he took a walk around the prison exterior, avoiding the guards both there, and at the Pemberton Buildings, another military prison close by. He then re-entered the tunnel, pulled a piece of wood over the top of the entrance to hide it from prying eyes, and made his way back to Rat Hell, arriving back there around three o’clock. He and Hamilton wanted to make their getaway immediately, but the others wanted to wait, so that they’d have a full night to make a clean break, rather than just the few hours before dawn. Reluctantly the officers agreed, and a schedule for exiting was arranged: each digger could bring another man with him, and there would be an hour’s gap between parties. If the tunnel wasn’t discovered, then the same thing could happen on a second and third night.

It was a great idea in theory. In practice, the following night, when the breakout began, chaos ensued, as word spread around the prison about the tunnel. Instead of a dozen or so men every hour, there was a constant stream of prisoners trying to get through, which quickly turned into a stampede. A false alarm suggesting guards were coming led to panic, with men trampled underfoot as they tried to return to their rooms, but still 109 men, starting with Rose and Hamilton, were able to get through the tunnel that night. The fireplace was put back in position to hide the tunnel down to Rat Hell, and the last man through had put the plank of wood back over the exit in the shed.

As far as the authorities were concerned, the disappearance of over a hundred soldiers was like a miracle. The roll call on Wednesday morning took four hours to complete, since the guards simply could not believe the disparity in numbers. The guards who had been on duty the previous night were immediately accused of complicity in the escape, since there seemed no other way that the Yankees could have achieved it, until two of the prison officers made a thorough inspection of the basement.

When they found the tunnel, they sent a young slave boy down through it, and joined him at the exit on the far side of the vacant lot. Rose’s calculations had been so exact that the prison guards were convinced the diggers must have had outside help to reach the precise spot they needed. The guards who had been locked up suspected of conspiracy were immediately released, “the manner of the escape being too evident”, as the
Daily Richmond Examiner
explained.

Four of the officers were recaptured, even before the escape had been discovered, some miles from Richmond. The fugitives had all taken separate routes as quickly as possible to minimize the chance of too many of them being caught. Four more were caught during Wednesday, fourteen further on Thursday. One soldier was caught by a freed slave, who asked where he was going. When told “nowhere”, the man marched the soldier to the authorities “with courage and patriotism worthy of immortality”, according to the
Enquirer.
Three fugitives gave themselves up after they went the wrong way on the river, and ended up nearly frozen. By Friday, thirty-four had been recaptured, although one, at least, had bluffed his way past a checkpoint.

By the end of the weekend, the total of recaptured Yankees had reached forty-eight, including Colonel Rose, who had had the misfortune to run into a group of Confederate soldiers who had disguised themselves in the enemy uniforms. When he realized his mistake, he tried to bluff his way out, but without success, and then, a few hours later, attempted to make a break for it, despite having a broken foot. He was apprehended by another patrol and returned to Libby. Quite a few of the prisoners were found still in Richmond, one of them caught by a newspaper boy as he tried to swap his Union Army jacket for a slave’s greatcoat. Some of them were unable to stop themselves from trying to attack Confederate soldiers they saw, and paid the price with their liberty.

Although most official sources today claim that only forty-eight were recaptured, with two drowned, contemporary newspaper reports note that fifty-eight had been returned by 20 February, and twenty-one were known to have reached safety in Fort Monroe or Williamsburg, including Major Hamilton. One of the remaining thirty was found on 21 February, meaning fifty in total succeeded in reaching their goal.

Those who returned to Libby were thrown into what one writer described as “a narrow and loathsome cell” and found a regime that had been unavoidably affected by the prison break. An alarm was raised when one guard thought he saw something – which turned out to be his own shadow. In the end, many of the key prisoners were exchanged: Colonel Rose was repatriated on 30 April 1864 and fought with conspicuous gallantry to the close of the Civil War.

Sources:

Daily Richmond Examiner,
11 February 1864: “Escape Of One Hundred And Nine Commissioned Yankee Officers From The Libby Prison”

Richmond Enquirer,
11 February 1864: “Extraordinary Escape From The Libby Prison”

Richmond Enquirer,
12 February 1864: “The Recent Escape from the Libby Prison – Recapture of Twenty Two Officers”

Richmond Enquirer,
13 February 1864: “Recapture Of More Yankee Officers”

Richmond Examiner,
15 February 1864: “The Re-Captured Yankee Officers”

Richmond Sentinel,
20 February 1864: “More Capture of Escaped Yankees”

Harper’s New Monthly
Magazine, April 1864: “My Escape from Richmond”

Moran, Frank E.,
Famous Adventures and Prison Escapes of the Civil War
(The Century Co., 1898)

National Tribune,
14 May 1885: “Libby Tunnel”

Civil War Richmond:
http://www.mdgorman.com/index.html
(An invaluable resource, with all of the contemporary news reports, many of which were referenced for this piece; the ones listed above are those from which specific details and anecdotes were taken.)

One of the largest mass escapes of the twentieth century occurred in Uruguay over forty years ago when over a hundred members of revolutionary group the Tupamaros tunnelled out of the Punta Carretas federal prison in the capital, Montevideo, leaving behind them a set of cheeky signs to taunt their guards. It was in keeping with the Robin Hood-like roots of the organization – and perhaps there’s a certain appropriateness to the fact that twenty years after the escape, the prison was turned into one of Uruguay’s most prestigious shopping malls. A McDonalds restaurant now resides in the feared prison administration building.

The Tupamaros were founded in the early 1960s by Raul Sendic, a former law student who had qualified as an attorney, but not quite finished his legal studies during the 1950s. He had become prominent in the Socialist Party of Uruguay, and took a great interest in the plight of the sugar-cane workers, helping to organize them into unions, and arranging marches on Montevideo. Their motto was “Por la tierra y con Sendic” (For the land and with Sendic), a slogan that was ironically left at the prison end of the tunnel that Sendic would organize while within Punta Carreta.