These two generals were models of their societies. Ulysses S. Grant was a rough and tumble tanner from Ohio. Robert E. Lee was a patriarchic southern aristocrat.

Lee is considered the better commander. He scored huge victories up until Gettysburg in 1863, while fighting against bigger and better supplied troops. In the victory at Chancellorsville, he divided his army three times in the face of the enemy while being outnumbered three to one, showing the use of speed and maneuvering to achieve his aims. He knew the South couldn’t just sit back and defend what it had. The North was too strong and some sort of early end to the war had to be found. Lee invaded the northern states twice. He hoped that a shock Union defeat in Pennsylvania or Maryland that could lead to a negotiated peace. Lee was increasingly seen as blameless. After the war, he was seen as a heroic, self-sacrificing soldier.

Grant’s military reputation suffers from his reputation as president, which historically is regarded as one of the worst Presidencies in U.S. history. Grant’s personal charisma was never as high as Lee’s. Grant seems to have been drunk a lot. Yet Grant was an exceptional general, managing to command all the Union armies. Grant made a plan and then stuck with it. He saved the Battle of Shiloh after the Union line was shattered on the first day, reorganizing his forces and counterattacking. “Whip ‘em tomorrow, though” he told Sherman at the end of an awful first day’s fighting—and he did. The siege of Vicksburg was a remarkable campaign of combined operations with the navy. Grant never rested in the final year of the war as he engaged Lee continuously from the Battle of the Wilderness to Appomattox. Grant recognized the new reality of warfare: because each side had such powerful weapons, the ability to maneuver was a key factor.

Grant beat Lee in the war.

Source: Which General Was Better? Ulysses S. Grant or Robert E. Lee?
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