Ulysses S. Grant and James Longstreet had one of the more remarkable friendships in American history, made all the more striking because they ended up on opposite sides of the Civil War.
They met as cadets at West Point in the early 1840s and became close friends despite their different backgrounds. Longstreet, a Georgian, was outgoing and physically imposing, while Grant was quieter and smaller, but they bonded over a shared dislike of military pretension and a love of horses. After graduation they served together in the Mexican-American War, where they fought alongside each other and deepened the friendship.
The personal connection became family. Longstreet was related to Grant’s future wife, Julia Dent, through his cousin. Longstreet attended Grant and Julia’s wedding in 1848 and, by some accounts, served as a groomsman or best man. The two men remained close until the Civil War divided them, with Longstreet becoming one of Robert E. Lee’s most trusted corps commanders and Grant rising to command all Union armies.
One of the most telling moments came in 1864, when Grant was given command of all Union armies and Confederate officers around Lee’s headquarters were dismissing him as a drunkard and a butcher who had only succeeded against second-rate Western generals. Longstreet, who knew Grant better than any man in gray, reportedly silenced the room by warning his fellow officers something to the effect of, “that man will fight us every day and every hour till the end of the war.” He told them not to underestimate Grant’s tenacity, that he was a soldier of singular determination, and that the Confederacy now faced an opponent unlike any it had met before. History proved him exactly right, the Overland Campaign that followed was the bloodiest and most relentless pressure Lee’s army ever endured.
What’s most touching is what happened after the war. When the two met again at Appomattox in 1865, Grant reportedly greeted Longstreet warmly, offered him a cigar, and invited him to play a game of cards “as if nothing had ever happened.” Grant later used his political influence to help Longstreet receive a pardon and restoration of citizenship. Longstreet then committed what many former Confederates considered an unforgivable betrayal: he became a Republican, supported Grant’s presidential campaigns, and accepted federal appointments from him, including minister to the Ottoman Empire. This earned Longstreet decades of vilification from Lost Cause writers, but he never wavered in his loyalty to his old friend.
James and Grant were good friends man, it was James who said don’t underestimate Grant. They didn’t listen.