Nova: What if the greatest strength of America's most famous general wasn't his strategy, but his history of failure? Before he was the hero of the Civil War, Ulysses S. Grant was a man adrift. A failed soldier, a failed farmer, a failed businessman, at one point so destitute he was reduced to selling firewood on a St. Louis street corner just to feed his family. So how does that man become the architect of one of the most stunning victories in military history?

Nova: Welcome to the show. Today, with the help of Ron Chernow's masterful biography, "Grant," we're joined by the wonderfully curious and analytical qing chen to explore this very paradox. Qing chen, it's so great to have you.

qing chen: It's a pleasure to be here, Nova. This book is a fascinating psychological portrait.

Nova: It really is. And that's the angle we want to take. Today we'll dive deep into this from two powerful perspectives. First, we'll explore the man before the legend, dissecting his years of intense struggle. Then, we'll connect that painful past to his most pivotal and surprising moments as a leader, revealing a side of Grant you've likely never considered.

Nova: So qing chen, let's start there, in that period of darkness before the war. Most people skip this part, but Chernow argues it's the whole foundation. And nothing illustrates this better than the story of the Grant & Ward scandal. It’s a moment of absolute devastation for him.

qing chen: It’s almost hard to read, it’s so painful. It feels like the final nail in the coffin of his self-worth.

Nova: Exactly. So for our listeners, here’s the scene. It’s the early 1880s, after Grant's presidency. He's a national hero, but he's always been terrible with money. He enters into a partnership with a young, charismatic financier named Ferdinand Ward. Ward is hailed as the "Young Napoleon of Finance." He promises Grant and his family astronomical returns, and for a while, the money just pours in. Grant, who has felt like a failure his whole life, finally feels successful and secure. He convinces friends and family to invest their life savings.

qing chen: And he trusts Ward completely. It's a blind trust, which is a key detail.

Nova: Utterly blind. Then, one day in May 1884, the floor falls out. Grant discovers that Ward is a complete fraud. The entire firm was a house of cards, a Ponzi scheme. There were no real profits, just money being shuffled around. In an instant, Grant is not just broke, he's ruined. He's lost his own money, his family's money, and the savings of everyone he convinced to invest. He's publicly humiliated.

qing chen: And Chernow includes a quote from Grant that I think is the key to his entire character. He says, "I could bear all the pecuniary loss if that was all, but that I could be so long deceived by a man who I had such opportunity to know is humiliating."

Nova: Yes! That's it right there. It wasn't about the money. It was the shame. The humiliation of being played for a fool.

qing chen: What strikes me is that this isn't just a financial failure; it's a profound failure of trust. He was betrayed by someone he admired, someone he brought into his family. You have to wonder how that experience—being so thoroughly deceived—reshaped his ability to judge character. It must have either made him incredibly cynical or, perhaps, incredibly attuned to the difference between performance and substance.

Nova: That’s a brilliant connection. He’d spent his life feeling inadequate, and this was the ultimate confirmation of that fear. He wasn't just poor again; he was a fool in the eyes of the world. This is his absolute bottom.

qing chen: And it's from that absolute bottom that he has to climb out. It’s a crucible. It either breaks you, or it forges you into something much, much stronger. For Grant, it seems to have forged a new kind of resilience, one that wasn't brittle or arrogant, but flexible and grounded in a deep understanding of what it means to lose everything.

Nova: That's a perfect bridge, qing chen. Because this man, stripped of everything and publicly shamed, is the same man who, twenty years earlier, makes one of the riskiest gambles of the war. Let's talk about the Vicksburg campaign.

qing chen: This is where the story gets so interesting. The connection between his past and his future actions.

Nova: Right. So, the situation is this: Vicksburg is the key to the Mississippi River. It's a Confederate fortress, and the Union army has been trying and failing to take it. The conventional military wisdom, championed by Grant's own generals like Sherman, was to maintain a long, secure supply line. You never, ever cut yourself off from your supplies. It's military doctrine 101.

qing chen: It's the safe play. The textbook move.

Nova: Exactly. But it wasn't working. The campaign was bogging down. So Grant does something that horrifies everyone. He decides to cut his army loose. He marches his men down the opposite side of the river, has his gunboats run the gauntlet of the Vicksburg batteries at night—an incredibly dangerous move—and then ferries his army across, deep in enemy territory, with no supply line. He decides they will live off the land.

qing chen: It seems like an act of pure madness to his contemporaries.

Nova: They thought he was insane! Sherman wrote that he felt "sadness" for Grant, believing the campaign was doomed. But here's the connection I want you to help us make, qing chen. How does the man who was ruined by the "safe" investment with Ferdinand Ward make this "insane" gamble?

qing chen: Well, it's not an insane risk if you've already faced and survived total ruin, is it? A man who has lost everything, who has been publicly humiliated, has a fundamentally different relationship with risk. For a general like Sherman, who had a reputation to protect, the biggest risk was a catastrophic failure. But for Grant, who had already experienced that, the bigger risk was inaction. The slow, grinding failure of a conventional siege was probably more terrifying to him than a bold gamble. He'd already seen how "playing it safe" and trusting the supposed experts could lead to disaster.

Nova: Wow. So his past failure recalibrated his definition of risk. That's fascinating. He wasn't reckless; he was just operating from a different set of assumptions, forged in his own personal fire.

qing chen: Precisely. He had a confidence that wasn't based on an unbroken string of successes, but on the knowledge that he could survive the absolute worst. That's a much more durable kind of confidence.

Nova: Let's jump forward to the end of the war, to another moment that defies convention: the surrender at Appomattox. Lee's army is defeated, and he meets Grant to discuss the terms. Everyone expects a harsh, punitive surrender.

qing chen: As would be typical. The victor dictates terms to the vanquished.

Nova: But Grant does something extraordinary. After drafting the terms, he looks up and notices Lee's officers are wearing their sidearms. He adds a line, unprompted, allowing them to keep their personal swords and pistols. Then, he makes an even more incredible offer. He allows the Confederate soldiers to keep their horses and mules. He says, "they will need them for the spring plowing."

qing chen: It's an act of stunning empathy. He's not thinking about punishing an enemy; he's thinking about helping a fellow countryman rebuild.

Nova: And this is the core of it. How does the so-called "butcher" general arrive at this moment of profound grace?

qing chen: It connects directly back to his own humiliation. Of course he let them keep their horses and their swords. He knew, intimately, what it was like to have your dignity stripped away in front of the world. He had been the man selling firewood, the man ruined by a swindler. He understood that the war was over, and the next, more difficult task was to rebuild a nation. And you can't do that by inflicting shame. He wasn't just accepting a surrender; he was trying to prevent the kind of deep, personal humiliation that he himself had endured. It's an act of profound empathy, born directly from his own suffering.

Nova: So when we look at the whole picture, it's this incredible arc. The very experiences that should have destroyed him—the failures, the poverty, the public shame—are the exact things that gave him the tools to win the war.

qing chen: It's a powerful lesson. His failure gave him resilience, it recalibrated his relationship with risk, and most importantly, it gave him a deep well of empathy that other, more traditionally successful leaders, might have lacked. He understood human dignity because his own had been so threatened.

Nova: It completely reframes how we should look at historical figures, and maybe even ourselves. We see the statues and the victories, but we miss the messy, painful, human story that made it all possible.

qing chen: Absolutely. And it leaves us with a really powerful question to think about in our own lives. It makes you wonder, when we look at our own setbacks, our own failures, are we seeing them as final judgments on our character? Or are we, like Grant, seeing them as the raw, and often painful, material that can be forged into our greatest future strengths?

Nova: A perfect thought to end on. Qing chen, thank you so much for helping us deconstruct this legend.

qing chen: It was my absolute pleasure, Nova.