Major General Daniel Sickles.  The most famous–some would say notorious–political general of the Civil War, Sickles’s actions on the battlefield contributed to the stunning Union defeat at Chancellorsville, and he almost lost Gettysburg as well (Library of Congress photo via the Civil War Trust) .    

This week marked the 150th anniversary of the Battle of Gettysburg, the epic clash that set the final course of the Civil War, even though months of bitter and bloody fighting would follow. After Gettysburg, Robert E. Lee and his storied Army of Northern Virginia could no longer threaten wide swaths of northern territory with all-out invasion, setting the stage for a decisive victory that force the Union to negotiate a peace with the Confederacy. And after Gettysburg, the rest of the war would be waged almost entirely on southern soil, through costly campaigns of attrition and logistics that Lee could not afford to fight, let alone win.

That is the essence of Gettysburg, the turning point of the war in the east. After a string of defeats, managed by incompetent generals, the Army of the Potomac finally beat Lee and forced him to retreat south, giving Union forces a desperately-needed shot of confidence. There would be more mistakes and bungles after Gettysburg, but for the army in blue, the road from that Pennsylvania rail hub inevitably led to Appomattox and final victory.

Still, Gettysburg’ s sesquicentennial raises inevitable questions that haunt historians–and generals–for centuries that follow? What if Lee’s best corps commander, Stonewall Jackson, had not been killed at Chancellorsville a few months earlier? Would his natural aggressiveness and prescient sense of the battlefield have led to the Confederates’ capturing the key high ground at Gettysburg on Day One or Day Two? Under that scenario, Gettysburg would have likely ended in a Union disaster, with Lee’s victorious forces taking Harrisburg and parading through Philadelphia within a week.

But Jackson’s potential impact on the battle is only one of the “what if’s” still being debated by historians and strategists. Suppose Lee had been in better health and relied less on his staff, which often delivered incomplete or inaccurate information for his decision-making. Or, what if Abraham Lincoln tarried and left General “Fighting Joe” Hooker in command of the Army of the Potomac for a few more days, instead of replacing him with George Gordon Meade? Bold as a planner but often timid in the field, it’s hard to imagine Hooker getting the best of Robert E. Lee at Gettysburg. And for that matter, what if Jeb Stuart’s Confederate cavalry had been properly positioned during the campaign? They spent much of the run-up to Gettysburg on the “backside” of Lee’s Army, denying him a key reconnaissance asset and badly-needed intelligence.

Still, the ultimate “what if” from Gettysburg may rest not at the army level, but instead, with a single Union corps commander who almost lost the battle–and the war–single-handedly. We refer to Major General Dan Sickles, the Tammany Hall politician who used his connections to wrangle a commission at the outset of the war, a move aimed at restoring his public image after being acquitted on murder charges!

Imagine Bill Clinton’s libido in the body of a 19th century politician who viewed a civil war as a golden opportunity to reinvent himself. That was Dan Sickles, a man once described by Harper’s Weekly as “loved more sincerely and hated more heartily than any other man of his day.” As a military leader, he was (arguably) the most incompetent general in a conflict that was filled with them. During his brief time in uniform, he almost managed to lose the war not once, but twice, yet survived his transgressions and lived into a ripe old age, shaping popular history to emphasize his “accomplishments” (while minimizing his own, disastrous mistakes), and lobbying–successfully–to receive the Congressional Medal of Honor, 32 years after the war ended.

Born to an upper-middle-class family in New York (his father was a politician and patent lawyer), Dan Sickles learned the printing business before becoming an attorney and running (successfully) for the state legislature. Controversy and scandal quickly became hallmarks his career; Sickles was censured by the New York legislature for escorting a known prostitute into its chambers. Undeterred, he later took her to England and presented her to Queen Victoria, introducing her under the surname of one of his political rivals.

Sickles sent the working girl home after his wife arrived in Europe, where he was serving as secretary of the U.S. Embassy in London. Naturally, the marriage had been scandalous; Sickles married his wife a few years earlier, when she was only 15 or 16 and he was 33. Returning to America in 1855, Sickles was elected to Congress as a Democrat. He remained a notorious womanizer but when his wife strayed, Sickles confronted her lover, Phillip Baton Key II, the District Attorney of Washington, D.C. and shot him dead (Key was unarmed). Sickles promptly surrendered to authorities, hired a high-priced legal team and beat the murder rap with a claim of temporary insanity–the first time that defense had been successfully used in an American court.

When the Civil War began, Sickles saw an opportunity for rehabilitation. He raised four regiments of volunteers in his native New York, and was appointed a Colonel in one of those units. Using his political connections, Sickles continued to rise in the ranks, and was promoted to Brigadier General in September 1861. Given his reputation–and complete lack of military experience–there was hesitation in Washington about giving Sickles flag rank and greater responsibilities; in fact, Congress initially refused to confirm his commission, forcing their former colleague to temporarily relinquish his command.

But once again, Sickles’ political ties paid off; he was not only restored to the rank of brigadier general, but President Lincoln nominated him for a second star in late 1862, and his good friend Joe Hooker–by then Commander of the Army of the Potomac–gave him command of III Corps a few months later. At the time, Sickles was the only corps commander in the Union Army who was not a West Point graduate. And while Sickles had proved competent leading a brigade at Seven Pines and the Seven Days engagements, he was clearly unprepared to lead a division, let alone an entire corps. His ineptitude would have near-cataclysmic consequences for the Union in the months that followed.

At the Battle of Chancellorsville, fought in early May 1863, Sickles was assigned to hold the center of the Union lines while Hooker attempted a risky, double envelopment of Lee’s forces. On May 2, advance elements of his III Corps observed large numbers of Confederate troops marching parallel to his lines. Sickles assumed the Rebels were retreating, but it was actually General Thomas “Stonewall” Jackson’s Corps marching around the Union flank, executing one of the most audacious (and successful) attacks of the war.

Assuming he could easily overtake and defeat the “retreating” Confederates, Sickles opened a wide salient in the Union lines, leaving his forces vulnerable to attacks from both sides, and isolating XI Corps. Lee and his commanders quickly took advantage of Hooker—and Sickles’s—mistakes, routing a Union force that was more than twice their size. Not surprisingly, Sickles’ effusive after-action report makes no mention of his errors, and he worked diligently to ensure that other summaries hewed close to his version of events.

General Hooker was relieved as Commander of the Army of the Potomac in late June 1863, literally on the eve of Gettysburg. Lee was already on the move, and the new Union commander, General George Meade, had no time to make changes among subordinates, or his headquarters staff. Given the opportunity, Meade would have almost certainly replaced Dan Sickles. While everyone agreed that the former politician was fearless on the battlefield, his poor judgment (and lack of military training) created the potential for catastrophe in combat

Making matters worse, Meade and Sickles openly detested each other; the III Corps commander had been a close associate of the departed Hooker (and believed that Meade played a role in his dismissal). From his perspective, Meade viewed Sickles as an amateur, more concerned about burnishing his “record” than following orders. Sickles, for his part, used his connections with the media to denigrate Meade at every opportunity, knowing that his new superior despised the press, and rarely defended himself in the papers.

Gettysburg was not a “planned” engagement; the collision of Confederate and Federal forces outside the small Pennsylvania town, coupled with key terrain, determined that the battle would be fought there. As Meade formulated his strategy, he ordered Sickles and III Corps to anchor the left end of the Union lines along key terrain including Cemetery Ridge and Little Round Top. On the morning of 2 July, Meade sent his son and aide, Captain George Meade, to ensure that Sickles had followed instructions. But General Sickles refused to talk with the younger Meade; eventually, he traveled to the commander’s headquarters and asked for help in positioning III Corps. Meade didn’t have time to inspect Sickle’s positions, but he sent his artillery chief to assist the Corps commander.

Returning to his unit, Sickles told the artillery commander that he wanted to move III Corps roughly ½ mile forward of the line ordered by General Meade Sickles believed the shift would put his troops in better defensive terrain, but it created tremendous headaches for Meade, and once again, left key elements of the Union Army badly exposed:

The primary disadvantage of Sickles’ position was that the Third Corps was too far in advance of Meade’s army to receive support. Meade’s reinforcements had to cover ½ mile of open ground and Sickles negated Meade’s interior lines. The essentially straight line along Cemetery Ridge, which Meade intended Sickles to occupy, was approximately 1,600 yards in length. Sickles’s Third Corps had roughly 10,675 effectives and he would later claim that he lacked sufficient strength to man Meade’s front. Yet the new position covered a front that was nearly twice as long; approximately 3,500 yards. Despite his efforts to refuse them, his flanks were in the air.

One of the biggest criticisms directed at Sickles was that by moving forward he abandoned Little Round Top— viewed by many as the key to the Union left because it was the highest defensible point in the immediate vicinity. Not a problem for Sickles because over the next 50 years he would repeatedly lie and say that he did occupy Little Round Top and supervised the placement of reinforcements up there.

By the time Meade became aware of Sickles’s move, Rebel artillery was already bombarding Union lines. It was too late for III Corps to return to its original position. General Meade was left with no choice but to reinforce Sickles’s line. As the Confederate attack unfolded, III Corps was pushed back with heavy losses and by late afternoon, Rebel forces (under the leadership of Lieutenant General James Longstreet) occupied most of Sickles’s modified position. However, III Corps elongated lines forced Longstreet to spread his forces over a wider front, slowing his assault. As darkness fell, Meade still occupied Cemetery Ridge, denying Longstreet—and Lee—the opportunity to win the battle on that day.

As for Sickles, he was wounded by a stray cannon ball around 6:30 pm, while attempting to rally his disintegrating forces. He was carried to the rear on a stretcher, puffing on a cigar and waving to his men. Sickles’s mangled right leg was amputated later that evening, and it soon became a key element of his self-proclaimed heroics. He donated the limb to the Army’s medical museum (where it remains on display to this day) and arranged quick transit back to Washington, where General Sickles received dozens of visitors and promulgated his own version of what happened at Gettysburg.

Sickles’s wound proved to be a blessing in disguise for the Union. It ended his career as field commander, though he later served as Military Governor of South Carolina before leaving the Army as a Major General. The rest of Dan Sickles life was just as colorful—and controversial—as his military career. After his wife died, Sickles became part of the U.S. diplomatic mission to Spain. In that role, he maintained his hard-drinking and womanizing lifestyle. According to some accounts, he fathered children with a deposed Spanish queen, and later married a noblewoman in Madrid. However, she quickly discovered that Sickles was a rogue and lived apart from him for most of the next 30 years.

Returning home once again, Sickles was elected permanent head of the New York state commission charged with raising money for civil war monuments and placing them on various battlefields. The former general remained in that post for years, until $28,000 turned up missing, and officials threatened to prosecute Sickles for embezzlement. Along the way, Sickles also blew through a $7 million fortune from his father, and won re-election to Congress. During his final terms in the House, Sickles focused most of his attention on preserving the Gettysburg battlefield. Once asked why there was no statue honoring him at Gettysburg, Sickles replied that the “entire battlefield” was his monument. He was also awarded the Congressional Medal of Honor in 1897, for his supposed heroism at Gettysburg.

Predictably, even Dan Sickle’s passing was steeped in controversy. He died in 1914, and was buried at Arlington National Cemetery, beneath a surprisingly modest headstone. But members of his family insisted that Sickles wanted to be buried at Gettysburg and they’ve spent the past century lobbying the government—unsuccessfully—to move him from Arlington to the battlefield in Pennsylvania.