Gideon Pillow: Coward, Liar and Scoundrel for the Ages (But, Oh, What a Name!)

The Glory of a Great Name

In the movie Shakespeare in Love, Christopher Marlowe and William Shakespeare are discussing Romeo and Ethel, the Pirate’s Daughter when Marlowe suggests the character Mercutio.  Later, Viola outlines the idea of Twelfth Night with a Duke Orsino.  “Good name,” Shakespeare says both times with admiration and a little envy, and I can entirely relate. As a writer, a good name can fill me with admiration, elation, and downright covetousness.  And so it was when, researching the Civil War, I stumbled across the perfidious Gideon Pillow.

As I pondered the near perfection of the moniker I could only sigh deeply. Since the real Pillow could not be incorporated into Beaufort 1849, and since naming a fictional character after a real person alive at the time could cause confusion, there was no way to include the glorious name in my book. I had to be satisfied with calling one of my characters Gideon Pickens, a weak echo at best. But there is more to Mr. Gideon Pillow than just his name! As Henry Birch says in Beaufort 1849, “My, my. We have a complete bounder on our hands.”

Born in Tennessee in 1806, Gideon Pillow practiced law in his home state as the partner of future president, James K Polk. Through his connections with Polk, he served as Brigadier General of the Tennessee Militia. Ten years later, when the Mexican-American War started up, Pillow deftly used political patronage to join the U.S. Army as a brigadier general. And then in 1847 President Polk promoted him to major general!  Lesson learned: make friends with those who will ascend to high places.

So far, so good. At the age of 41, Pillow appeared to be a rising star in the military. But then he made the mistake of crossing General Winfield Scott, commander of American forces in Mexico.  Now, “Old Fuss and Feathers” Scott is considered by many historians to be one of the ablest generals in American military history. (He was also responsible for at least a portion of the terrible human toll during the Cherokee removal from Georgia, but that’s another story.) After the major action of the war--action during which Pillow had altogether shown a great deal more incompetence than competence--Pillow felt he hadn’t received enough recognition and glory. So under the pseudonym “Leonidas,” he sent letters to the New Orleans Daily Delta and Picayune newspapers, as well the American Star and the Pittsburgh Post, crediting himself for recent American victories at Contreras and Churubusco. (Interesting to see that even in that day and age people worked the news media spin.)

Can't beat the caption above

Scott, however, knew very well that Pillow had done next to nothing to achieve those victories and that others deserved the credit.  When the dastardly letters were exposed as Pillow’s handiwork, Scott arranged for a court of inquiry into the matter.  Believing Scott’s actions politically motivated, President Polk came to the defense of his former law partner and recalled Scott to Washington. During the court of inquiry investigation, Pillow persuaded Major Archibald Burns to claim authorship of the letters and publicly take the fall for him. It was not widely believed however, and Pillow was discharged from the army all the same.

Said Scott in his memoirs, Pillow was "amiable and possessed of some acuteness, but the only person I have ever known who was wholly indifferent in the choice between truth and falsehood, honesty and dishonesty:—ever as ready to attain an end by the one as the other, and habitually boastful of acts of cleverness at the total sacrifice of moral character.”

Always ambitious, Pillow went on to try for the nomination for vice president but failed twice, in 1852 and again in 1856.  His next shot for public glory would be the Civil War. 

When the war began, Pillow joined the Confederate army as a brigadier general in the Western Theater.  He is best remembered for two battles, the first being the Battle of Fort Donelson.  Fort Donelson was a Confederate stronghold in Tennessee that protected the vital manufacturing and arsenal city of Nashville.  The battle turned out to be Ulysses S. Grant’s first big success, and indeed was a vital victory for the North at a time when the Union army was showing little progress at all.

Now Fort Donelson was under the command of Brigadier General John B. Floyd, a political appointee who, although he had been Secretary for War for the United States right up until nearly the Secession, had no actual experience in conducting war.  Second-in-command was our friend, Gideon Pillow, who in theory had experience in the Mexico, but as we know was really a fraud who tended to talk big and do little.

Confederate troops at Fort Donelson numbered 18,000, whereas Grant had about 25,000 Union troops at his disposal.  To capture a fortified position generally took a three to one advantage in numbers, so you can see Grant had almost no business even considering attacking Fort Donelson.  But fresh from his victory over nearby Fort Henry (mostly due to the badly-engineered Fort Henry conveniently flooding the Confederates out) Grant was confident of success at Fort Donelson as well.  It turns out this confidence was largely due to his knowledge that Gideon Pillow was in command inside that fort.  Said Grant in his memoirs:

Pillow deflator

“I had known General Pillow in Mexico, and judged that with any force, no matter how small, I could march up to within gunshot of any intrenchments he was given to hold. I said this to the officers of my staff at the time. I knew that Floyd was in command, but he was no soldier, and I judged that he would yield to Pillow’s pretensions.”

And Pillow did not disappoint! And yet to be fair, Pillow did actually achieve success in battle before he managed to completely screw it up.  With the fort surrounded in large part by Union troops, the Confederate officers knew things looked bad for them, so at dawn Pillow directed an assault of 10,000 men into the unprotected right flank of the Union line in an attempt to open up an escape route.  This way they would cede the fort but not lose the men.

Surprisingly, luck went with him. Pillow had a massive force filled with talented men, among them Nathan Bedford Forrest, and he had the advantage of surprise. Not expecting the Confederates to take action that morning, Grant was away consulting with a gunboat officer too wounded to come and make a report to him.  Other than telling his underlings to stand their ground, he didn’t leave much in the way of instructions, so when Pillow’s forces attacked, they found unorganized resistance, brigadier generals unwilling to help each other without explicit orders from Grant, and troops who were curiously clueless about how to resupply themselves with ammunition even when there was plenty lying about in boxes on the ground. 

After a few hours of heavy fighting, the Confederates pushed through and the escape route was clear!  The Confederate troops fought with backpacks of three days provisions on their backs.  They were ready to head to south to safety.

The heat of battle

It was right about then that Grant returned from his visit to his wounded officer.  Much to his surprise he found a battle going on, a battle in which his side was being routed. Wounded and demoralized men were everywhere; noise, smoke and chaos abounded.  Characteristic of Grant, he didn’t freak out.  (No matter how bad things were, Grant never freaked out, a good quality in a general.)  He quickly figured out that the Confederates were pressing for escape not a combat victory, he determined where they would be weakest, and he started giving orders.  From his memoirs:

 “I directed Colonel Webster to ride with me and call out to the men as we passed: ‘Fill your cartridge-boxes, quick, and get into line; the enemy is trying to escape and he must not be permitted to do so.’  This acted like a charm.  The men only wanted some one to give them a command.”

He had one general attack the enemy's west side, the other the enemy’s east.  And then Grant had his turn of luck in the expected form of Pillow’s bad judgment.  Just when the Confederates had created their escape route, and indeed, were halfway to leaving, for some incomprehensible reason Pillow decided to regroup and resupply his troops before pushing forward.  To the amazement of all he ordered his troops back into their trenches, and all advantages gained by the Confederates that morning were lost. Grant quickly exploited the opening given to him, and by the end of the day the Union army was poised to take the fort.

That night was a bad one for the Confederate leadership.  General Floyd was edgy. Having committed what amounted to treason as U.S. Secretary of War (shipping arms from northern armories to southern ones to better position the South when Secession came was just one example of why the North might like to hang him), he decided to skedaddle out while the going was good and offered the command of the 18,000 troops to his second-in-command, Gideon Pillow.  But Pillow then decided that it was also too dangerous for him to be captured for reasons known only to himself.  So he handed the command to third-in-command, Brigadier General Simon P. Buckner who accepted responsibility for the welfare of the troops, and Floyd and Pillow fled in the dark of night.  Nathan Bedford Forrest, furious at the general level of incompetence and stupidity, said, “I did not come here to surrender my command,” and stormed out.  He also left during the night, escaping with his cavalry of 700 by mucking through swamps and fording swollen creeks to the south.

Though the next morning Grant would accept nothing less than unconditional surrender from Bruckner, he and Bruckner were old buddies from West Point and the Mexican war.  They discussed Pillow’s flight the previous night, and how Pillow had expressed concern that his capture would be a disaster for the Southern cause.

"He thought you'd rather get hold of him than any other man in the Southern Confederacy," Buckner told Grant.

"Oh," replied Grant, "if I had got him, I'd let him go again. He will do us more good commanding you fellows."

The fall of Fort Donelson and the loss of so many men was difficult for Pillow to spin, though he did try.  But his next battle, the Battle of Stones River, where Major General Breckinridge found Pillow cowering behind a tree and had to order him forward, spelled the end for Pillow’s combat assignments.  Though he went on to administrative positions in the Confederate army (where he could do less damage), he had successfully earned for all time the distinction of being one of the worst generals in American history.