Ulysses S. Grant spent the night of April 6, 1862 in misery.

His ankle was throbbing from a riding injury he suffered a few days previous. A torrent of rain swelled the western bank of the Tennessee. Artillery shells from gunboats thundered all night. Grant could hear his soldiers screaming as they received amputations at a makeshift hospital.

On the Confederate side, victory appeared imminent. At that moment, General P.G.T. Beauregard even telegrammed Jefferson Davis with news of overrun Union armies. Beauregard would later say he thought he had “Grant just where [he] wanted him.”

It’s hard to argue with that conclusion. It was the first night during the Battle of Shiloh, ending what was (up until then) the bloodiest day of the Civil War. The Confederates had won the day.

At around midnight, General William T. Sherman found Grant underneath a tree with a cigar in his hand.

“Well, Grant,” Sherman said. “We’ve had the devil’s own day, haven’t we?”

Grant looked up, mid-puff, and said:

“Yes. Lick ‘em tomorrow, though.”

From Failure to Failure…

Why is Grant’s optimism remarkable? 

It’s that he hadn’t just had a hard day. 

He’d had a hard life

Consider a brief resume of Grant’s experiences up to that point:

  • Graduated in the bottom half of his class at West Point
  • In his 20s, Grant joined a “temperance lodge”–a sort of 19th-century rehab
  • After the Mexican-American War, cholera broke out during a long escort to San Francisco.
  • Tried several businesses during the 1850s, all of which failed
  • Separated from his wife during one assignment, he took to drinking again
  • He resigned from the Army thanks to one particularly bad drinking episode
  • Had to take a job in Galena, Illinois, working for his father
  • Grant farmed on his brother-in-law’s property in Missouri. He failed at this, too (malaria)
  • Eventually resorted to selling firewood to make a living
  • Having failed again, Grant took a job with his father in Illinois
  • “When the war started,” says biographer Ron Chernow, “he was working as a clerk, junior to his two younger brothers, in his father’s leather goods store in Galena, Illinois.”

That’s right: Ulysses S. Grant started the year of 1861 as a failed veteran of the Mexican-American War.

He didn’t even have the privilege of commanding his own younger brothers at the leather shop.

Three years later, he was commanding the entire American army. Within the decade, he was President.

What exactly happened there?

…Without Loss of Enthusiasm

Grant might have looked like a failure to some. But if there’s a difference between failing well and failing poorly, Grant usually chose the former.

  • He didn’t just fight in the Mexican-American war; he fought with distinction. He once rode a horse through under sniper fire, hiding by hanging off the horse’s side as he rode; all that just to deliver a message. He later said that he developed his “moral courage” in the war.
  • He didn’t just cross Panama; he took charge during the cholera outbreak. He organized the construction of a hospital and saw to treatment. When fearful doctors avoided nursing patients back to health, Grant stepped in and did it himself.
  • He didn’t just farm in a slave state; he refused to own another human being. At a time when Grant was earning just $50 a month and deeply in debt, he inherited a slave named William Jones. Selling the slave might have fetched Grant $1,500. He could have taken the immoral way out of his dilemma and betrayed his principles. He didn’t. He freed Jones instead.

Grant’s life hadn’t gone how he wanted it to go. Yet when the Civil War started, Grant went straight into it with enthusiasm as if he expected—of all things—success. 

At the Battle of Fort Donelson, an intimidating Confederate assault had the Union army in disarray. Grant’s life experience should have taught him to expect failure. To panic and retreat.

Instead, he asserted command. He cut through the confusion and rallied the troops. He even rode seven miles over icy terrain to coordinate the orders himself.

The next day, the Confederates surrendered. U.S. Grant, a man who never surrendered to life, instead earned the nickname “Unconditional Surrender Grant” for the surrender he imposed on others.

Which brings us to Shiloh.

Winston Churchill once said that success is going from failure to failure without loss of enthusiasm.

“Lick ‘em tomorrow, though,” is a nice summary of Grant putting this philosophy into practice. Failure kicked Grant around, but it never knocked him down. It never stole his mojo. It never made him blind to opportunity or circumstances.

When Grant freed William Jones rather than sell him to fatten his own wallet, that was the act of a man who expected, eventually, to recover from his troubles with his dignity in tact. Grant never let his desperation get the best of him. Grant’s strange mix of razor-sharp strategic assessment and completely unfounded optimism for the future was exactly what the Union needed.

The day after “Lick ‘em tomorrow,” reinforcements arrived and the Union army turned the tide of the Battle of Shiloh.

Critics claimed all sorts of things: Grant had been drunk during the first day; the casualties were too many to bear; Buell, commander of the reinforcements, had been the one truly responsible for the victory.

Abraham Lincoln refused to remove him, saying:

“I can’t spare this man; he fights.”

Grant fought on. At Vicksburg, at Chattanooga, at Appomattox, and at the ballot box (twice), he would win.