It was a grim errand that sent Abraham Lincoln hurrying toward Alton, Illinois, early on the morning of September 22, 1842. At Alton, he would cross the Mississippi River to a small island over the Missouri border-Bloody Island. There, he would prepare himself to kill or be killed in a saber duel to the death.

The idea of Lincoln fighting a duel begs a burning question for the perennial speculator, the intensely curious sort of history aficionado who wonders what might have happened if Major General George Meade had pursued the Army of Northern Virginia after the Battle of Gettysburg, or if Lieutenant General Thomas ‘Stonewall’ Jackson had survived his wounds at Chancellorsville. The question is this: What if Abraham Lincoln had been killed by a saber slash in 1842? It could have happened by the hand of 36-year-old James Shields if events had gone differently on September 22, 1842. Before circumstances turned Shields and Lincoln into mortal enemies, the two politicians had had a peaceable, professional relationship. They had been in the Illinois state legislature together, Lincoln having won election as a Whig in 1834, and Shields, as a Democrat in 1836. Illinois had an enormous debt in the late 1830s and early 1840s, and the legislature had its hands full just keeping the government operating. In 1837, as the state bank teetered on the brink of collapse, Whigs and Democrats fought over what to do. Lincoln and Shields, however, were able to negotiate a compromise that saved the banks. On one key issue of the time–building new infrastructure such as railroads and other public works–the Whig party wanted private corporations to own the facilities. Democrats favored state ownership. Shields, though faced with heavy pressure from his party, often supported private ownership. So, despite party differences on major issues, Shields and Lincoln often managed to land on the same side of the final vote.

When the state bank defaulted in 1842, however, there was no such camaraderie. Shields, now the state auditor, aligned with the state’s governor and treasurer to adopt a policy in which the state would refuse to accept its own paper money as payment of taxes and other debts. Lincoln cleverly assailed this sitting duck of a policy, simultaneously striking a blow at the Illinois Democratic party in general and at Shields in particular. In a letter to the editor of the Sangamo Journal published in the paper on September 2, 1842, Lincoln presented a polemic designed to embarrass Shields. He chose the Journal as his forum because he had fairly free rein in the paper’s columns; editor Simeon Francis was friendly to him and sympathetic to his views. Mrs. Francis had even opened her home as a rendezvous for Lincoln and his future wife, Mary Todd.

Lincoln offered up some pungent prose in his letter to the editor. He began with an earthy character, Jeff, complaining to the rough-hewn but shrewd Rebecca: ‘I’ve been tugging ever since harvest getting out wheat and hauling it to the river, to raise State Bank paper enough to pay my tax this year, and a little school debt I owe; and now just as I’ve got it…, lo and behold, I find a set of fellows calling themselves officers of State, have forbidden to receive State paper at all; and so here it is, dead on my hands.’

When Rebecca identifies Shields as one of the ‘officers of state’ and reads aloud from his declaration against accepting state money, Jeff explodes. ‘I say–it-is-a-lie…. It grins out like a copper dollar. Shields is a fool as well as a liar. With him truth is out of the question.’

Lincoln went on to deride his adversary on the social scene, with Jeff recalling Shields at a recent fair attended by the eligible women of Springfield. ‘His very features, in the ecstatic agony of his soul, spoke audibly and distinctly–‘Dear girls, it is distressing, but I cannot marry you all. Too well I know how much you suffer; but do, do remember, it is not my fault that I am so handsome and so interesting.’

The letter ended with an appeal to the editor: let your readers ‘know who and what these officers of State are. It may help to send the present hypocritical set to where they belong and to fill the places they now disgrace with men who will do more for less pay….’ Lincoln signed it ‘Rebecca.’

Before sending the letter to the Journal, Lincoln showed it to Mary Todd and her friend Julia Jayne. The two women had a grand time helping Lincoln sharpen his barbs. They apparently got carried away with excitement of the situation; later, they picked up where Lincoln left off and wrote a letter of their own, a feeble aping of Lincoln’s cutting wit that ended with a derisive verse signed ‘Cathleen.’ Shields was an amusing if volatile target for taunting. Lincoln’s future presidential secretaries John Nicolay and John Hay, both familiar with the Illinois capital and its characters, described him as ‘a man of inordinate vanity…, an irresistible mark for satire.’ Shields’s law partner, Gustave Koerner, said, ‘He was exceedingly vain and very ambitious, and like most ambitious men, on occasions, quite egotistical… In his manner he was peculiar, not to say eccentric.’

Needless to say, Shields was incensed by the Rebecca letter. In an effort to get to the bottom of the situation, Shields asked Francis for Rebecca’s true identity. Francis responded, as Lincoln had instructed him, that it was Lincoln. Lincoln, of course, had had help, but apparently he wanted to keep Mary Todd out of it. If the reason for that protective measure was not obvious at the time, it would become so on November 4, 1842, when he married her. On finding the source of his public humiliation, Shields, emotionally wounded and furious, had a menacing note hand-delivered to Lincoln in Tremont on September 17. ‘I have become the object of slander, vituperation and personal abuse,’ Shields wrote. Only a full retraction ‘may prevent consequences which no one will regret more than myself.’ Lincoln discussed the predicament with his friends Dr. Elias Merryman, a Springfield physician, and William Butler, the clerk of Sangamon County Court, and decided not to retract his pointed words. Shields was not appeased and again demanded ‘absolute retraction.’ Lincoln refused, suggesting that Shields take back his hand-delivered letter and submit one that was more ‘gentlemanly.’ There would be no further negotiation. Shields challenged Lincoln to a duel.

As the party who had been challenged, Lincoln got to set the fight’s conditions. He did so on September 19 in a letter that demonstrated a personal trait that historian Gary Wills has described as ‘letting nonsense work itself out to its own demise.’ First, Lincoln selected ‘cavalry broad sword of the largest size’ rather than pistols as the dueling weapons. ‘I did not want to kill Shields and felt sure I could disarm him…,’ he later wrote, adding, ‘I didn’t want the d—-d fellow to kill me, which I think he would have done if we had selected pistols.’ Next, Lincoln prescribed conditions so advantageous to himself that his opponent would be forced to write off the martial affair as a lost cause. He ordered ‘a plank ten feet long, and from nine to twelve inches abroad, to be firmly fixed on edge, on the ground, as the line between us, which neither is to pass his foot over upon forfeit of his life.’ Such unusual conditions would allow Lincoln to take advantage of his superior reach; Shields was only five feet, nine inches tall, while Lincoln soared to six feet, four inches. Once again Lincoln had underestimated Shields. Shields was an ambitious, perseverant man, and his professional experience proved that. He had been a state legislator and now was the state auditor. He had been in the Black Hawk War, and during the Mexican War and Civil War, he would serve as a brigadier general. In the 1840s and 1850s he would win elections to the U.S. Senate–first representing Illinois, then Minnesota, then Missouri. In Minnesota, he would found a town and name it Shieldsville. Such a driven and determined man fights stubbornly over his reputation.

Stubbornness was only one of the characteristics that led Shields to the dueling field in September 1842. He also had courage in the face of death. During the Mexican War, he would take a bullet in the chest at the Battle of Cerro Gordo. After surgery and nine weeks of recuperation, he would return to command. This was clearly not a man who would run away from a fight to the death. So, on September 22, 1842, Shields left Illinois, where dueling was illegal, for Missouri, where it was allowed. He walked ashore onto Bloody Island ready to kill Lincoln or be killed by him.

Fortunately for Shields and Lincoln, shared friends John J. Hardin, a relative of Mary Todd, and Dr. R.W. English sped to the duel scene-at least as much as anyone could speed in a small boat in 1842-and pleaded with the would-be combatants to let bygones be bygones. It was a truly desperate attempt to bring peace, but it worked. The duel was cancelled. Though the incident ended without violence, Lincoln avoided talking about it, preferring to forget it ever happened. In a letter written on December 9, 1865, Mary Lincoln recalled that an army officer visiting the White House asked her husband, ‘Is it true…that you once went out, to fight a duel and all for the sake of the lady by your side?’ Lincoln replied, ‘I do not deny it, but if you desire my friendship, you will never mention it again.’

Despite his bad experience with heavy-handed sarcasm, Lincoln did not retire his acerbic wit. Stephen A. Douglas, Lincoln’s Democratic opponent in the 1858 election for one of Illinois’s seats in the U.S. Senate, learned that firsthand. Lincoln roasted Douglas to a crisp during a debate in Charleston on September 18, and that display was not a one-time happening. Major General George B. McClellan, who received many kind words from Lincoln early in the Civil War, also knew the sting of Lincoln’s sarcasm. Annoyed by McClellan’s slowness in attacking Confederate armies in Virginia in late 1861 and early 1862, Lincoln referred to McClellan’s massive Army of the Potomac as ‘McClellan’s bodyguard.’ He remarked that if McClellan did not care to use his army for fighting, he ‘would like to borrow it.’

Lincoln never again got tangled up in the makings of a duel. Shields, on the other hand, found himself involved in such proceedings in 1850, when on behalf of Democratic Congressman William H. Bissell, he presented the acceptance of a challenge to a duel issued by future Confederate president Jefferson Davis. But he immediately set to work settling the matter without violence. He was successful. Lincoln and Shields apparently settled their differences, or at least agreed to disagree. During the Civil War, Shields was nominated for the rank of brigadier general in the Union army. Final approval fell to the president-Lincoln. He approved. With that move some 20 years after the duel that was not, Lincoln publicly buried the cavalry broadsword.

This article was written by Louis Vargo and originally published in the February 2002 issue of Civil War Times Magazine.

For more great articles, be sure to subscribe to Civil War Times magazine today!