Friday, March 20, 2026

Grant and Longstreet: A Lesson in Irony

I'm loving this biography.


I'm only 100 pages into it and already I sense a master biographer at work -- good storytelling, an engaging narrative, and a nuanced portrayal (no hagiography here). The author has a great eye for detail. I feel like I'm right there with Grant as the life of our 18th president is laid out with as much showing as there is telling. 


One day in 1854 after Grant had been forced to retire from the army and had taken up poor dirt farming, he ran across James Longstreet in St. Louis. Longstreet was shocked to see how poorly dressed his old friend was and how far down the social ladder he had tumbled. Grant pressed a 5 dollar gold piece into Longstreet's hand to repay a 15-year old debt. "You must take it," insisted Grant after Longstreet refused. "I cannot live with anything in my possession which isn't mine." Longstreet reluctantly accepted the money. At Grant's wedding, James Longstreet had served as his best man. Later, Longstreet and two of Grant's groomsmen would join the Confederate army. 


All three would later surrender to Grant at Appomattox. 

The war is full of such ironies. Irony reminds us that outcomes often contradict intentions. The world never operates exactly as we expect it to. We are constantly being forced to analyse the gap between what we think will happen and what actually occurs. This is one reason historians have always found it difficult to decipher Ulysses S. Grant. 

Don't read this book unless you're prepared to rethink your predisposed biases about the man. Frankly, I'm having trouble putting it down.