Tales from the Trenches

The Confederate Spymaster Sleeping With the Enemy

Confederate generals relied on Thomas Jordan for key intelligence on Union troops—and he led them straight into a disastrous battle.

05.08.16 4:45 PM ET

SHILOH BATTLEFIELD, Tennessee—It’s rare in history that spymasters get credit for victories, but, then again, only occasionally are they blamed for disasters. Few are so bold or so foolish as to declare that something is an absolute fact, as CIA Director George Tenet did when he told President George W. Bush the intelligence confirming Saddam Hussein had weapons of mass destruction was a “slam dunk.”

No, the language of espionage is a language of qualification. Do the Iranians have a nuclear weapons program? A key National Intelligence Estimate in 2007 concluded they sort of didn’t but, then again, might just. (“We judge with high confidence that in fall 2003, Tehran halted its nuclear weapons program; we also assess with moderate-to-high confidence that Tehran at a minimum is keeping open the option to develop nuclear weapons.”)

One can imagine the frustration of presidents, or for that matter, generals, when they get that kind of fact-fudged information. So the question often becomes, for them, less about what information can trusted than about whose information and whose judgment can be trusted, and that person, whether as spymaster, chief of staff, or with some more mysterious title, becomes the bearer of good news, bad news, and, most importantly, trusted news.

But that person is not in the public eye. The leader he or she reports to gets the credit or the blame. And when it comes to the military, the spymaster or staff officer remains in the shadows, without a command, and without a reputation; a footnote in hundreds of histories, the central figure in few or none.

Such a man, here at the horrific Battle of Shiloh in April 1862, was Adjutant-General Thomas Jordan, who had been Confederate Gen. Pierre Gustave Toutant Beauregard’s right-hand man since before the first Battle of Bull Run the year before, who would stay with him through most of the war, and who defended Beauregard’s reputation ferociously—one might say as if it were his own—ever afterward.

Shiloh, which took place almost one year after the Rebel attack on Fort Sumter that started the American Civil war, was the first truly bloody battle in a conflict that eventually turned slaughter into an industrial activity. At Shiloh there were more casualties (killed, wounded and missing) than in all the previous American wars combined: from the Revolution to 1812, from the Halls of Montezuma to the shores of Tripoli, the carnage pales by comparison.


On the first day of the battle that raged around a little log-cabin church called Shiloh and the banks of the Tennessee River at a riverboat landing called Pittsburg, the Confederates under Generals Albert Sidney Johnston (who was killed) and P.G.T. Beauregard (who was sick) pushed the Federal troops back dramatically, capturing their camps and more than 2,000 men, including a general.

As night fell on April 6, 1862, the commanding general of the Federal Forces, Ulysses S. Grant, managed to stop the Confederate advance just in time to keep his army from being pushed into the Tennessee River. But Beauregard was sure that the next day he’d be able to finish the job.

In the event, however, 13,000 Federal reinforcements under Gen. Don Carlos Buell arrived overnight, allowing the Federals to sweep the Confederates off the field on April 7.

In the middle of all this, Adjutant-General Jordan, with the rank of colonel, with no troops of his own, managed to command major deployments on the battlefield in the name of his superiors, and mismanaged information with such cool and confident ineptitude that he helped snatch defeat from the jaws of victory.

But before we get into that, let’s look at Jordan’s earlier activities.  

He was born and brought up in Virginia’s Shenandoah Valley at a town called Luray, now famous mainly for enormous caverns.

Jordan went to West Point and graduated with the Class of 1840, two years after Beauregard. One of Jordan’s classmates was George H. Thomas, the Union general who earned the nickname “the rock of Chickamauga.” Another classmate—in fact his roommate—was William Tecumseh Sherman, who would play a critical role at Shiloh.

In the Seminole Wars and the Mexican War in the 1840s, even as a young lieutenant, Jordan earned a reputation as an organizer. In Mexico he was with the first unit to cross the Rio Grande, and, having risen to a position as the de facto quartermaster of the operation, he was the last American soldier to leave when American troops withdrew.

Jordan served in various Southern garrisons, and on the Pacific Coast. But by 1860 he was back serving in Washington, D.C., secession was in the air, and Jordan, a Virginian, knew where his loyalties lay. There was, for him, none of Robert E. Lee’s angsting about loyalties.

As early as 1860, the then-governor of Virginia and former member of Congress, the unfortunately named John Letcher, wanted to build a spy network in Washington. The man he called on to do this job was Jordan, although, of course, Jordan neglected to mention this new role to his commanders in the Federal Army.

In fact, Jordan did not resign his commission in the Federal Army until May 1861, when Virginia joined the Confederacy. In the meantime, and it had been a long meantime, Jordan had used his position and Letcher’s contacts among Washington’s Southern-sympathizing social elites to build a network of several agents.


One of the most important, and eventually the most famous, was Rose Greenhow, a rather sere but evidently charming 44-year-old widow who entertained and was entertained at the upper levels of Washington society where, as one Union agent put it, she “used her almost irresistible seductive powers.”

Greenhow was well known in the capital as a Southern sympathizer. She had wept openly in the Senate Gallery in January 1861 when Sen. Jefferson Davis gave his farewell speech to go join the Confederacy. (A few weeks later he became its president.) But the politics of women, whether spies or otherwise, were not taken seriously, so Greenhow’s opinions were no deterrent to northern senators who sought, and apparently thought they had, her affections.

Historians at the CIA have published a little monograph on the ad hoc intel networks of the Civil War that gives a concise rundown of Greenhow’s suitors. Sen. Henry Wilson of Massachusetts, who chaired the Committee on Military Affairs, persisted in courting her even when he knew that Lincolns’ Pinkerton detectives were on his tail: “Spies are put upon me but I will try to elude them tonight and once more have a happy hour in spite of fate,” he wrote, signing the letter “H.” Another besotted member of the military affairs committee was Sen. Joseph Lane of Oregon. Greenhow counted the military secretary of Gen. Winfield Scott, commander of the Union armies, among her good friends, as well, and apparently tried to persuade him to defect.

Jordan taught Greenhow to use a simple 26-symbol cipher, and to address her correspondence to Thomas John Rayford, his pseudonym. The messages were delivered through what was called the “Secret Line,” a collection of men and women organized by the Confederate Signal Corps to act as couriers across enemy lines.

Within weeks after joining the Confederate army, Jordan was on Beauregard’s staff in Virginia while Greenhow and her collaborators remained in D.C.  As the first great battle of the war approached around the Manassas railroad junction and the creek called Bull Run in northern Virginia, Jordan was kept informed of Union troop movements “by as romantic a set of spies as any general ever had in his service,” writes Beauregard biographer T. Harry Williams.

“Mrs. Greenhow dispatched her first message in early July,” writes Williams: Union army commander Irvin McDowell would advance on July 16, it reported.

“It was carried from Washington by a beautiful girl named Bettie Duvall, who disguised herself as a country girl and rode in a farm wagon to Virginia,” writes Williams. “Going to the home of friends, she changed her costume to a riding habit, [and] borrowed a horse.” Then she rode to the Confederate outpost at Fairfax Courthouse.

Duvall told the officer in charge that she had an urgent message for Beauregard. “Upon my announcing that I would have it faithfully forwarded at once,” the officer later said, “she took out her tucking comb and let fall the longest and most beautiful roll of hair I have ever seen. She took then from the back of her head, where it had been safely tied, a small package, not larger than a silver dollar, sewed up in silk.” Within was the message for Beauregard.

“At this time,” as Williams writes, “volunteer girl spies from northern Virginia were bursting into Beauregard’s lines at every turn, bearing news that the Yankees were coming. They were received with consideration and applause, although their information was generally vague and available in Washington newspapers. To secure more definite news, Jordan sent a man named Donellan to Mrs. Greenhow. He carried a scrap of paper on which Jordan had written in cipher, ‘Trust bearer.’ He reached Washington on July 16 and received from her a coded message saying McDowell had been ordered to move on Manassas that night.”  

In fact that intelligence was not vital to the Confederate victory in the battle that began five days later. But documents incriminating Rose Greenhow were found by advancing Union troops. She was put under surveillance by the famous detectives of Alan Pinkerton, who acted as Abraham Lincoln’s FBI. Her house at 398 16th St., NW, just south of the White House, was described by one Federal agent as “a sort of focal center where treason found a resting place and where traitors were supplied with every needed care and where they were furnished with every possible information to be obtained by the untiring energies of this very remarkable woman.”

Eventually Greenhow was placed, secretly, under house arrest, so the Feds could pick up anyone who paid a call; later she was imprisoned. In June 1862 Greenhow, now a celebrity ex-spy, finally was sent through Federal and Confederate lines to Richmond.

By then, Jordan had some explaining to do. After Greenhow’s capture, the cipher that he had devised apparently was used for deceptive messages sent by Union officers. Writing about the cipher to the Confederates’ then-Secretary of War Judah P. Benjamin, Jordan said, “Being my first attempt, and hastily devised, it may be deciphered by any expert, as I found after use of it for a time.”

Jordan stayed with Beauregard, and accompanied him west, where one of the largest forces ever assembled by the Confederates was gathering to defend a crucial rail crossing at the little town of Corinth, Mississippi. General Albert Sidney Johnston was in overall command, but Beauregard was his number two, and Johnston often deferred to him—which meant Jordan’s intelligence gathering was supposed to serve both, and he availed himself of the authority of his connections to both.

At least one scholar of the war later concluded that Johnston and Beauregard were “the victim[s] of a sadly inexpert intelligence service.” Certainly the romantic days in which beautiful young city girls flocked to the Confederate officers with information about troop movements were pretty much gone, and Jordan was relying on more conventional means to gather information.


In late March 1862, Confederate Brig. Gen. Benjamin Hardin Helm
, who happened to be Abraham Lincoln’s brother-in-law, was sent on a scouting mission. The Confederates knew that Grant and some 48,000 troops were camped in or near the banks of the Tennessee River about 20 miles north of Corinth. They also knew there was a good chance that another Union general, Don Carlos Buell, was on his way to the area with well over 10,000 more troops. Helm’s mission was to find out where Buell was, where he was headed, and when.

In the first day or so of April, Helm reported back that Buell’s forces would link up with Grant’s by April 6.

That turned up the heat in Corinth, where Johnston and Beauregard had been planning what they hoped would be a surprise attack against Grant’s forces before he could lay siege to their position—and before he could be reinforced.

On the night of April 2, at just about 10 p.m., by Jordan’s own account, he and a Confederate officer named Jacob Thompson, who had been secretary of the interior under President James Buchanan until a year before, were in Jordan's office when a telegram arrived.

A general about 20 miles north of Corinth and west of Grant's position had seen a large body of Union troops maneuvering there. The implication was that Grant might be readying an attack on Corinth from two directions, on the one hand, and his forces were divided, on the other.

By Jordan’s account, Beauregard had seen the telegram and put a note on it saying the time to attack was now, and telling Jordan to go tell that to the commanding general, Albert Sidney Johnston.  Beauregard himself was sick. A chronic throat infection had grown severe, so he was relying on Jordan to handle the matter that night, and Jordan was only too happy to oblige.

Jordan read Thompson the telegram, then they went a quarter mile to Johnston's office, where they found him surrounded by his personal staff. Johnson read the telegram and Beauregard's note, then they all went to talk to another top general, Braxton Bragg, who was in his nightshirt. Bragg agreed with Beauregard, but Johnston did not.

Johnston, cautious, said the troops were too raw for an offensive like this (some were only days in service, many carried only the weapons they'd brought from home), the battleground would be terrain chosen by the Union, and Johnston had doubts about whether he had enough reserves for such a fight.

Now Jordan spoke for Beauregard, countering Johnston’s objections, and Johnston, finally, gave in.

There and then, Jordan wrote out orders for the army to be up, armed and on the move within about five hours—at 6:00 a.m. “Jordan read Gen. Johnston, the commander, a “rough draft” of these orders, which were supposed to be Beauregard’s orders, and Johnston approved.

In the early morning, Jordan took notes Beauregard had scribbled on envelopes and scraps of paper and wrote them up as the official order of battle.

The deadlines were, of course, impossible to meet, but over the course of the next day, 44,000 Confederate troops were on the move toward Shiloh. Rain and mud and disorganization slowed them down, and it was not until April 5 that they made it to within a couple of miles of the Union lines, 24 hours later than planned. And by then Beauregard himself was having his doubts about the whole undertaking.

Jordan had learned from a captured Union officer that the Union troops were not dug in and, amazingly, had no idea what was coming at them. “They don't expect anything of this kind back yonder,” as the prisoner put it. But Beauregard could not believe that Union officers, including Jordan’s old West Point roommate, William Tecumseh Sherman, could be so blind to the coming Confederate onslaught.

Johnston, probably fed up at this point, said the die was cast.


The fighting on that first day was ferocious and confused as Sherman and other commanders at first, indeed, did refuse to believe they were facing a major attack, then marshaled their forces to put up stiff resistance, but had to fall back to new positions again and again.

Some of the fiercest fighting took place around a road that cut across the center of the battlefield. Troops under Union Gen. Benjamin Prentiss, a politician and militia commander out of Illinois who had fought in the Mexican War, held their ground hour after hour until at last they were surrounded. Prentiss was forced to surrender with 2,200 of his men.

Grant pulled his forces back to a strong defensive line along the top of a steep ravine, with artillery batteries deployed in force and two Federal gunboats firing massive shells at the Rebels’ right flank, but, still, it felt to many of his officers like a last stand.

Early in the afternoon, a stray bullet, almost spent, cut an artery in Johnston’s leg and he bled to death before anyone knew exactly what had happened. Beauregard was now in charge, and as the sun went down on fields and forests littered with corpses, Beauregard called a halt to the Confederate push, sure that he could restore order in his own ranks, regroup and mop up Grant’s battered forces the next day, as long as Grant was not reinforced.



So, intelligence about Buell was crucial, and Jordan, who had ridden out to the battle lines, was the man handling it.

Earlier in the day, a telegram had arrived in Corinth from Brig. Gen. Helm (the Lincoln brother-in-law), who had predicted a few days earlier that Union Gen. Buell and his masses of fresh troops would be arriving at Grant’s camp just about this time. But the new message, which had to be brought from Corinth to the battlefield and to Jordan by a mounted courier, said otherwise. It claimed that scouts tracking Buell saw him headed not toward Grant, but toward the town of Decatur, Alabama, about 100 miles away.

Jordan gave the dispatch to Beauregard, who clearly wanted to believe it, and as far as we can tell, Jordan did not do much to disabuse him of his optimism. Indeed, Jordan wrote out a telegram from Beauregard to officials in the Confederate capital, Richmond. His forces had “gained a complete victory,” said the Beauregard-Jordan telegram, “driving the enemy from every position.”

By now, the camp was lit by lanterns and fires, and Jordan was surprised to see a senior Union officer there: Gen. Benjamin Prentiss, who had put up such resistance at the Hornet’s Nest earlier in the day, only to be captured along with more than 2,000 of his men.

Col. Thompson, the former interior secretary, was there, too, and it turned out he and Prentiss were old friends. So, despite the horrors of the day—the thousands upon thousands killed and wounded on both sides—the conversation became fairly friendly banter. (One imagines more than a bit of whisky was consumed as well, but there’s no record of that.)

And then, the three of them bedded down together, literally. As Jordan wrote, “Colonel Thompson and myself, with General Prentiss sandwiched between us, shared a rough makeshift of a bed made up of tents and captured blankets.”

Prentiss “talked freely of the battle, as also of the war, with a good deal of intelligence and good temper,” and, laughing, he said: “You gentlemen have had your way to-day, but it will be very different tomorrow. You'll see! Buell will effect a junction with Grant tonight, and we'll turn the tables on you in the morning.”

In the meantime, a relatively unknown Confederate cavalry officer named Nathan Bedford Forrest had dressed some of his men in the coats of dead Yankees and sent them out in the dark to reconnoiter. They came back to Forrest with word that Buell had indeed arrived, but Forrest could not find Beauregard, and those commanders he could find after midnight, not including Beauregard or Jordan, didn’t believe him.

Back in the main camp, sleeping with the enemy, as it were, Jordan thought Prentiss sounded sincere, but might be pulling his leg. So he answered “in the same pleasant spirit” and “showed him the dispatch that had reached me in the field” from Helm saying Buell was headed for Alabama. Prentiss, apparently an amazing loudmouth, “insisted, however, that it was a mistake, as we would see.”

“Tired as we were with the day's work,” Jordan wrote, “sleep soon overtook and held us all until early dawn, when the firing first of musketry and then of field-artillery roused us, and General Prentiss exclaimed: ‘Ah! Didn't I tell you so! There is Buell!’ And so it proved. The combined forces of Grant and Buell swept the Confederates from the field.”

If ever there was a “sadly inexpert” intelligence service, surely Thomas Jordan’s was it. Yet his reputation seems to have survived. Indeed, in the late 1860s, Cuban revolutionaries recruited him to be their commander in chief. He trained them to fight like a regular army, without a regular army’s resources, and left their families to be massacred by the ruthless forces of Spain. In the end, he decided the better part of valor was to resign and go back to the United States, where the erstwhile spymaster became a journalist.