The Three Cigars That Changed The Civil War

The Battle of Antietam, fought on September 17, 1862, was one of the most consequential engagements of the American Civil War. It marked the bloodiest single day in American military history, with over 22,000 casualties. Amid this pivotal moment, a misplaced envelope containing three cigars and Confederate General Robert E. Lee’s Special Order 191 altered the war’s trajectory in a way that continues to intrigue historians.

General Lee’s Ambitious Gamble

By September 1862, emboldened by Confederate victories, General Robert E. Lee aimed to bring the war to Union territory. His Special Order 191 outlined a plan to divide his army for strategic maneuvers, with copies distributed to his generals under strict secrecy. However, one copy, wrapped around three cigars, was left behind at a Confederate campsite near Frederick, Maryland.

The Discovery of the Cigars and Special Order 191

On September 13, 1862, Union soldiers of the 27th Indiana Infantry discovered the cigars and orders. Recognizing the importance of the document, they passed it up the chain of command to Union General George B. McClellan.

McClellan, upon reading the orders, declared, “Here is a paper with which, if I cannot whip Bobby Lee, I will be willing to go home.” The Union now possessed detailed intelligence on Lee’s movements, presenting a rare opportunity to strike a decisive blow.

The Role of the Cigars: Coincidence or Symbolism?

The discovery of cigars alongside Special Order 191 raises questions about their role—practical, symbolic, or purely coincidental.

1. Practical Significance

The cigars may have served as a soldier’s indulgence, included in the envelope for convenience. Their presence may have made the bundle noticeable to the Union soldiers who found it.

2. Symbol of Southern Leadership

Cigars, often associated with Southern aristocracy, evoke an image of the Confederacy’s perceived grandeur. Ironically, this symbol of status became part of a costly mistake for Lee’s campaign.

3. Symbol of Chance in War

The cigars have taken on symbolic meaning as a reminder of the role chance plays in war. Their discovery, while incidental, had monumental consequences, highlighting how seemingly small details can shift the course of history.

Antietam: The Bloody Outcome

Armed with Lee’s plans, McClellan moved to intercept the Confederate forces. However, his characteristic caution prevented him from fully exploiting the intelligence. The result was the Battle of Antietam, a brutal confrontation that ended in Lee’s retreat to Virginia.

Though tactically inconclusive, the Union declared a strategic victory, providing President Abraham Lincoln the opportunity to issue the Emancipation Proclamation, changing the war’s scope and stakes.

The Cigars’ Legacy

The cigars and Special Order 191 have become enduring symbols of the unpredictability of war. Whether as a practical artifact or a symbol of chance, they remind us of how minor details can influence major events. McClellan’s handling of the intelligence remains a point of historical debate, as the Union’s missed opportunity to decisively crush Lee prolonged the war.

Conclusion

The envelope containing three cigars and Special Order 191 is a fascinating artifact of the Civil War, emblematic of the fragile interplay of chance and strategy. Whether viewed as a stroke of luck or a careless blunder, the cigars add a layer of intrigue to one of history’s most pivotal moments. The Battle of Antietam reminds us that even the smallest, seemingly inconsequential details—like three cigars wrapped in an envelope—can alter the destiny of nations.

Previous
Previous

The War of 1812: The Roots of Cigar Smoking in America

Next
Next

The Cigars of Pre-Civil War and Civil War America