Face-off: American Civil War Commanders Quiz

Thomas "Stonewall" Jackson earned his nickname at the First Battle of Bull Run in 1861, when another Confederate general supposedly pointed to him holding firm under fire and shouted, "There is Jackson standing like a stone wall!" He would end up becoming one of Lee's most trusted lieutenants, leading rapid, unpredictable maneuvers that kept Union forces off balance. His 1862 Shenandoah Valley Campaign became a masterclass in using speed, deception, and audacity to defeat larger forces. Jackson's aggressive leadership played a major role in Confederate victories at Second Bull Run, Fredericksburg, and especially Chancellorsville, where his famous flank attack helped rout the Union army.

Unfortunately for the Confederacy, Chancellorsville was also where Jackson's career ended. While scouting at night, he was accidentally shot by his own men, leading to pneumonia after his arm was amputated. He died in May 1863, and Lee reportedly said Jackson had "lost his left arm, but I have lost my right."

Nathan Bedford Forrest was the cavalry crusader of the Confederacy. He was fearless, ruthless, and wildly effective. A self-made businessman with no formal military training, Forrest quickly earned a reputation for fast raids and brutal tactics, as well as striking where the Union least expected it. He played key roles in battles across Tennessee and Mississippi, including at Fort Pillow, where his troops were accused of massacring surrendering African American soldiers.

After the war, Forrest's life didn't change much. He became one of the early leaders of the Ku Klux Klan, a brand new organization dedicated to terrorizing freed slaves and violently opposing Reconstruction. Later, he reportedly distanced himself from the Klan's violent activities and even called for its dissolution, but the damage was done. He spent his final years trying to rebuild his fortune and reputation, dying in 1877. (The extent to which he had an actual change of heart or if was just trying to clean up his legacy remains a point of dispute.)

Joshua Chamberlain was a college professor turned Union officer who proved that sometimes the best battlefield training is, well... none at all. As commander of the 20th Maine at Gettysburg in 1863, he famously held the extreme left flank of the Union line at Little Round Top. When his men were nearly out of ammunition, Chamberlain ordered a bayonet charge that drove the Confederates back, an act equal parts desperation and brilliance that very well may have saved the Union position that day. He went on to fight in several more campaigns, earning a reputation for bravery and an impressive collection of battlefield wounds.

After the war, Chamberlain served four terms as governor of Maine and later as president of Bowdoin College. In 1893, in a show of poor timing, he was awarded the Medal of Honor for his actions at Gettysburg. He also returned to the public eye at Appomattox, where Grant chose him to oversee the formal Confederate surrender, and Chamberlain ordered his men to salute their former foes, a gesture of reconciliation that he would never stop telling people about.

He died in 1914, still carrying one of his wartime wounds, making him one of the last Civil War generals to pass away. Chamberlain remains a darling of Civil War buffs, remembered as the scholarly soldier who turned a bayonet charge into a historical highlight reel.

Braxton Bragg was the Confederate general best known for... well, being stubborn and unpopular. He commanded the Army of Tennessee and fought several key battles in the Western Theater, including Perryville, Stones River, and Chickamauga. While Chickamauga was a rare Confederate victory under his leadership, his frequent clashes with subordinates and questionable decisions often undermined his own efforts. Some historians say his greatest enemy was his own temper.

After repeated failures and complaints, Bragg offered his resignation in 1863, was a bit ticked off when it was accepted eagerly, and then spent the rest of the war in less influential roles. He never quite recovered his reputation and retired to a quiet life after the Confederacy fell, dying in 1876.

After some modest early assignments, Ulysses S. Grant gained attention by capturing Fort Henry and Fort Donelson in 1862, where he famously demanded "unconditional surrender" from the Confederates and earned himself an enduring nickname in the process. One of his greatest triumphs came with the Siege of Vicksburg in 1863, which split the Confederacy in two by giving the Union full control of the Mississippi River. Promoted to command all Union armies in 1864, Grant pursued a war of unceasing pressure against Robert E. Lee, grinding down the Confederate forces until Lee's surrender at Appomattox in April 1865. Grant's style was simple: keep hitting the other guy until the other guy couldn't get back up. Subtle? Nope. Effective? You bet.

After the war, Grant traded his army uniform for politics, running for president in 1868 on the strength of his reputation as the man who saved the Union. He served two terms, overseeing Reconstruction and pushing for civil rights protections for African Americans. His administration, however, became infamous for corruption scandals, largely because Grant's loyalty to friends was stronger than his skill at spotting crooks. After leaving the White House, he went on a world tour, was treated like royalty abroad, and returned home to discover he'd been financially wiped out by a bad business deal.

In his final years, while battling throat cancer, Grant turned to writing his memoirs, encouraged by Mark Twain. He finished them just days before his death in 1885, and they became both a critical success and a financial lifeline for his family. Today, he's remembered as the quiet, stubborn man who won America's deadliest war.

James Longstreet was one of Robert E. Lee's most trusted generals and arguably the Confederacy's best corps commander. He fought in nearly every major Eastern battle, including Second Bull Run, Antietam, and Gettysburg, where his cautious advice to attack the Union flanks instead of launching Pickett's doomed charge famously went unheeded. Known for his solid defensive tactics and calm under fire, Longstreet was often the steady hand trying to rein in Lee's more energetic impulses.

After the war, Longstreet's reputation took a nosedive among Southerners because he supported Reconstruction and even worked with the Republican Party, views seen as betrayal by many former Confederates. He held several government posts, including diplomat and railroad executive, trying to rebuild both his career and the shattered South. Longstreet died in 1904.

William Tecumseh Sherman made his mark as the Union general who believed war should be as unpleasant as possible, at least for the enemy. After solid service at Shiloh and the capture of Atlanta in 1864, he began his infamous March to the Sea, carving a path of destruction through Georgia. His goal was to break the Confederacy's will to fight, and he did it with ruthless efficiency: burning supplies, tearing up railroads, and generally making sure Southern infrastructure would need a very long vacation before functioning again.

After the war, Sherman stayed in the Army, serving as general-in-chief after Grant became president. He oversaw western expansion campaigns, which, from the Army's perspective, meant moving Native Americans off their lands. Offered the Republican nomination for president, he declined with the famous line, "I will not accept if nominated and will not serve if elected," making him the patron saint of people everywhere who really, really don't want that job.

Remember the kid who would buy all the Star Wars action figures and keep them in the package? That's George B. McClellan. He was the Union general who could organize an army like nobody else, all while stubbornly refusing to actually use it, causing Abraham Lincoln at one point to quip, "If you don't want to use the army, I would like to borrow it for a while."

Given command of the Army of the Potomac in 1861, he whipped it into a well-drilled, well-supplied force, but his cautious nature turned nearly every campaign into a masterclass in missed opportunities. During the Peninsula Campaign in 1862, he advanced toward Richmond at a leisurely pace, always convinced he was outnumbered (he wasn't). Even after the Union's success at Antietam, he let Robert E. Lee slip away, which finally convinced President Lincoln to relieve him.

After his military career stalled, McClellan turned to politics. In 1864, he ran for president against Lincoln as the Democratic nominee, promising to negotiate peace with the Confederacy. He lost decisively, and Lincoln kept his job at least for a little while, thanks in large part to victories by Sherman and Grant.

Postwar, McClellan tried his hand at engineering projects and served as governor of New Jersey from 1878 to 1881, a role that suited his managerial strengths far better than battlefield command. He died in 1885, remembered as the Union's great organizer and as the man who, in Lincoln's words, suffered from a bad case of "the slows."

What can I say about Robert E. Lee? He was the Confederacy's most celebrated general, admired and adored for his tactical skill and gutsy maneuvers. Taking command of the Army of Northern Virginia in 1862, he won a string of victories against larger Union forces, including the Seven Days Battles, Second Bull Run, and Chancellorsville. His invasions of the North, however, ended somewhat less triumphantly, at least for the south. Antietam killed his momentum with a lot of men, and Gettysburg in 1863 delivered a defeat his army never fully recovered from. By 1865, facing Ulysses S. Grant's relentless pressure, Lee surrendered at Appomattox Court House, bringing the war effectively to a close.

After the war, Lee declined offers to profit from his fame and instead became president of Washington College in Virginia (later Washington and Lee University), promoting education and reconciliation, although his vision of reunion notably excluded full equality for African Americans. He avoided public political battles, preferring a quieter role in shaping the next generation of Southern leaders. He died in 1870.

Winfield Scott Hancock was one of the Union's most reliable field commanders, earning the nickname "Hancock the Superb" for his smart leadership. At Gettysburg, he took command of the Union center on the battle's second day, managing the defense and playing a key role in repelling Pickett's Charge. Known for leading from the front, sometimes to a fault, he was seriously wounded at Gettysburg but returned to service as soon as he could walk without falling over.

After the war, Hancock stayed in the army, overseeing Reconstruction in Louisiana and Texas, where his respect for civil liberties earned him both praise and criticism. In 1880, the Democrats nominated him for president, largely because he was a war hero with no major political baggage. He lost narrowly to James Garfield, proving that being "superb" on the battlefield doesn't guarantee success at the ballot box, while Garfield proved that success at the ballot box can prove hazardous to one's health.