Olivia: Alright Jackson, quick—if Harriet Tubman had a modern-day LinkedIn profile, what would her job title be? Jackson: Oh, easy. 'Executive Director of Freedom, specializing in high-risk extractions and logistics management. Unbeatable track record. References available upon survival.' Olivia: That is... shockingly accurate. And it’s a perfect entry point for the book we’re discussing today, Harriet Tubman: The Road to Freedom by Catherine Clinton. Jackson: I'm glad you think so! Because the version of Harriet Tubman I grew up with was more of a saintly, historical figure. The 'Executive Director' version sounds a lot more compelling. Olivia: That's exactly the point. Clinton's biography was part of a wave of new scholarship in the early 2000s. The goal was to rescue Tubman from the realm of folklore and children's stories, to show the brilliant, strategic 'Executive Director' behind the legend, not just a one-dimensional hero. Jackson: I love that. So we're getting the real, gritty story of the strategist, not just the symbol. Olivia: Precisely. And to understand the strategist, you have to start long before she ever ran. You have to start with her mother.

Jackson: Her mother? I don't think I know anything about her parents. I always assumed her story began with her own escape. Olivia: That's what most people think. But Clinton makes it clear that the seeds of defiance were planted early. Harriet Tubman was born Araminta Ross, or "Minty," and her mother was a woman named Harriet Green, but everyone called her Rit. And Rit was a force of nature. Jackson: Okay, I'm intrigued. What did she do? Olivia: There’s this incredible story from the book. Their owner, Edward Brodess, was in debt and planned to sell one of Rit's sons to a slave trader from Georgia. This was the ultimate terror for an enslaved family—being sold "down the river" to the brutal cotton or sugar plantations of the Deep South, a virtual death sentence. Jackson: A fate they'd do anything to avoid. Olivia: Anything. So, Rit gets wind of this. She hides her son for over a month. Finally, the owner and the Georgia trader corner her at her cabin, demanding she bring the boy out. Jackson: This sounds like a no-win situation. What could she possibly do? Olivia: She stood in the doorway and delivered one of the most powerful lines in the entire book. She looked her master in the eye and said, "The first man that comes into my house, I will split his head open." Jackson: Wait, she threatened her master with an axe? And it worked? That feels like it should have been a death sentence for her. Olivia: It was an unbelievable gamble. But the book explains the complex dynamics of the Eastern Shore of Maryland. It wasn't the Deep South. There was a large free Black population, and some owners had a strange, twisted dependency on their enslaved families. In this case, her sheer, terrifying resolve worked. The Georgia man gave up and left empty-handed. Brodess, the owner, backed down. Jackson: Wow. So young Harriet—or Araminta—grew up hearing this story? Knowing that defiance was possible? Olivia: Exactly. It became family lore. It taught her that the system, as absolute as it seemed, could be challenged. It showed her that a single, determined person could stare down power and win. That lesson is the bedrock of everything she does later. Jackson: That completely reframes her story. It wasn't a spontaneous act of courage; it was learned. But her life was still brutal, right? I remember hearing about a head injury. Olivia: It was horrific. As a young teenager, she was at a dry-goods store when an overseer was trying to capture an enslaved man who had left the fields without permission. The man ran, and the overseer ordered Araminta to help restrain him. She refused. Jackson: Just like her mother. Olivia: Just like her mother. She stood in the doorway, blocking the overseer's path. In a rage, the overseer grabbed a two-pound lead weight from the counter and hurled it at the escaping man. But he missed. The weight struck Araminta directly in the head. Jackson: Oh my god. That should have killed her. Olivia: It nearly did. She was unconscious for days, bleeding, with no medical care. Her owner actually tried to sell her while she was still recovering, but no one would buy "damaged goods." The injury left her with lifelong, debilitating headaches and what we now believe was temporal lobe epilepsy. She would suddenly fall into a deep sleep, almost like a coma, sometimes in the middle of a sentence. Jackson: So these spells... they must have been a huge liability, especially later on the Underground Railroad. Olivia: You would think so. But this is where her story takes another turn. Araminta was deeply religious, and she didn't interpret these episodes as a disability. She saw them as a direct line to God. During these spells, she had powerful visions and heard God's voice guiding her. Jackson: So what a doctor today might call a symptom of a brain injury, she experienced as divine revelation? Olivia: Precisely. And she trusted it implicitly. These visions became a core part of her strategic toolkit. She believed God was showing her the way, warning her of danger, and telling her when to move. It gave her a level of certainty and fearlessness that was, frankly, superhuman. This is how Araminta Ross, the injured girl, starts to become Harriet Tubman, the liberator.

Jackson: Okay, so she has this foundation of defiance from her mother and this... divine guidance system from her injury. How does that transform her into the legendary 'Moses'? Olivia: The legend of "Moses" came later, but the methods started with her own escape in 1849. After she made it to Philadelphia and tasted freedom, she felt an unbearable loneliness. She famously said that she was a stranger in a strange land and that her home was with her family. So, she went back. Jackson: Which is just mind-boggling. Most people would just be grateful to be free. Olivia: But she wasn't most people. Her first major rescue was her niece, Kizzy, and her two children, who were about to be sold. She coordinated the escape with Kizzy's husband, a free Black man named John Bowley. It was a complex, multi-stage operation involving boats, secret handoffs, and hiding places in Baltimore. It was a success, and it proved she could do it. Jackson: So she was already a strategist from the very beginning. What about the famous nickname, 'Moses'? Olivia: That grew over time as she made more and more trips. But what's crucial to understand is that 'Moses' wasn't just a guide. She was a general. She used spirituals, like "Go Down, Moses," as coded signals to let people know she was in the area. She often started her rescue missions on a Saturday night, knowing the runaway notices couldn't be printed in the papers until Monday morning, giving her a crucial head start. Jackson: That's brilliant. It's pure tactical thinking. Olivia: And she was ruthless when she had to be. She carried a pistol, and not just for show. Her policy was simple: if someone lost their nerve and wanted to turn back, she would point the gun at them and say, "You'll be free or die." Jackson: Wow. Move or die. Olivia: Because one person turning back could betray the entire group. The stakes were too high. Her famous boast was, "I never ran my train off the track and I never lost a passenger." That policy was a big reason why. Jackson: That adds a layer of steel to the saintly image. It makes her more real. But all her trips were for family, initially? Olivia: Mostly. But the most heartbreaking trip was for her husband, John Tubman. He was a free man, and she went back for him in 1851, bringing him a new suit she'd bought. But when she got to his cabin, she discovered he had taken another wife and had no interest in leaving. He told her he was fine where he was. Jackson: That's devastating. To risk everything for someone who has already moved on... I can't even imagine that feeling of rejection and betrayal. Olivia: Clinton describes it as a moment of profound pain for her. But what Harriet did next is what defines her. Instead of retreating in grief, she found a group of eleven other enslaved people who wanted to escape, and she led them on one of her most dangerous journeys yet. This was the trip that took her all the way to Canada. Jackson: Why Canada? Weren't the Northern states free? Olivia: They were, but the Fugitive Slave Law of 1850 made them incredibly dangerous. The law empowered slave catchers to hunt down fugitives even in so-called free states and forced citizens to help them. After the betrayal by her husband, Tubman decided America itself was no longer safe. She said, "I wouldn't trust Uncle Sam with my people no longer, but I brought 'em clear off to Canada." Canada became her new Promised Land.

Olivia: And that commitment to her people, to getting them to true safety, didn't stop at the Canadian border. In fact, her most audacious act was yet to come, and it's the part of her story that is criminally overlooked. Jackson: More audacious than being the most famous conductor on the Underground Railroad? What could possibly top that? Olivia: Becoming a military commander. When the Civil War broke out, Harriet Tubman didn't just sit on the sidelines. She went to South Carolina and offered her services to the Union Army. At first, they used her as a nurse and a cook, but they quickly realized her true value. Jackson: Her knowledge of the land and her network of contacts. Olivia: Exactly. She became a spy and a scout. She could move through Confederate territory without raising suspicion. She built a network of local informants—enslaved people who knew the terrain, the troop movements, the supply lines. She was providing critical intelligence to the Union commanders. Jackson: So she went from leading small groups to freedom to running a spy ring. That's an incredible evolution. Olivia: It gets better. In June of 1863, she planned and co-led a military raid up the Combahee River in South Carolina. This wasn't just scouting; this was a full-blown armed assault. She had gathered intelligence on where the Confederates had placed underwater mines, or "torpedoes" as they called them. She guided the Union gunboats past the dangers, deep into enemy territory. Jackson: You're kidding me. She was leading U.S. troops into battle? Olivia: She was. The gunboats landed, soldiers set fire to plantations, and as the fires raged, hundreds of enslaved people ran from the fields and swarmed the boats. The chaos was immense. Tubman later described the scene, saying the slaves were like "a black tide" rushing to the ships, some with pigs squealing on their backs, others with pots and pans. In one night, they liberated over 750 people. Jackson: Seven hundred and fifty people. In one raid. That's more than she freed in a decade on the Underground Railroad. And she led it. That makes her the first woman in American history to lead an armed military operation. Olivia: It absolutely does. It was a stunning victory, both militarily and symbolically. It shattered the Confederate myth of the "loyal slave." And it was planned and guided by a Black woman who had once been enslaved herself. Jackson: So after all that—hero of the Underground Railroad, war hero who led a successful raid—she must have been celebrated, right? Honored by the government for her service? Olivia: And this is the final, bitter irony of her story. After the war, she returned to Auburn, New York, and lived in poverty. She spent thirty years fighting the U.S. government for a military pension for her service as a soldier and a spy. They denied her again and again, citing lack of official records. Jackson: That's infuriating. They used her expertise, she won them a victory, and then they erased her from the paperwork? Olivia: It's a story that feels depressingly familiar. She was even physically assaulted on a train once, with the conductor refusing to accept her military pass and having four men throw her into the baggage car. She was swindled out of her life savings in a gold scam because she was so desperate for money. Her fight for freedom didn't end when slavery was abolished. It just became a fight for dignity, for recognition, and for simple justice.

Jackson: It's an incredible story, but also an infuriating one. Her fight truly never ended. She was battling the system her entire life, from the plantation to the pension office. Olivia: Exactly. And that's the core of what Catherine Clinton's book reveals so powerfully. Harriet Tubman's legacy isn't just a historical monument to be admired from a distance. It's a living, breathing story of relentless persistence against impossible odds. Jackson: It makes her famous quote feel so much more profound. The one about keeping on. Olivia: It does. She famously said, "If you are tired, keep going; if you are scared, keep going; if you are hungry, keep going; if you want to taste freedom, keep going." That wasn't just a slogan for the fugitives she was leading through the swamps. It was the principle she lived by her entire life. Jackson: From escaping bondage, to facing down her own master's threats, to fighting for a pension after the war was won. She just kept going. Olivia: She did. She eventually won a small pension, not for her own service, but as a soldier's widow. And with what little she had, she fulfilled her final dream: founding a home for the aged and poor, a place of refuge for others. Jackson: It makes you wonder, who are the Harriet Tubmans today, fighting battles we don't even see? The ones who are tired and scared, but just keep going. Olivia: That's a powerful question. And maybe the best way to honor her legacy is to ask ourselves that. We'd love to hear what our listeners think. What does her story of 'Keep Going' mean to you in your own life? Let us know. Olivia: This is Aibrary, signing off.