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America's Greatest Grifter? The Odd Story of Appleton Oaksmith: Presumed Slave Trader, Confederate Spy, and Voting Rights Activist

Our American Stories / Lee Habeeb
The Truth Network Radio
May 19, 2025 3:02 am

America's Greatest Grifter? The Odd Story of Appleton Oaksmith: Presumed Slave Trader, Confederate Spy, and Voting Rights Activist

Our American Stories / Lee Habeeb

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May 19, 2025 3:02 am

Appleton Oakesmith, a man born into privilege, took to the sea and led the U.S. on a wild goose chase that became a political crisis in 1864. He was involved in the slave trade, worked as a Confederate blockade runner, and was eventually pardoned by Ulysses S. Grant. Oakesmith's life took a remarkable turn when he became a pro-black civil rights politician in North Carolina, advocating for black political rights and civil rights in the state legislature.

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Let's get into it. Appleton Oakesmith's mother was a woman named Elizabeth Oakesmith and she was a very prominent first-wave feminist. She was a lecturer, an essayist, a poet, a playwright, a journalist. She traveled in literary circles. She was friends with Edgar Allen Poe, Henry Wadsworth Longfellow, Horace Greeley.

She would speak on behalf of women's rights but she was also in favor of ending slavery. And to give you a sense of how progressive she was in her time, she got the state of New York to legally change her kids' last names. She either thought the last name Smith was too boring or she didn't want her kids to have her husband's surname. She went by Elizabeth and then her middle name Oakes and then her husband's last name Smith. Her son's last name is Oakesmith as one word without the ES.

It's just kind of smushed together. I am convinced that if the story hadn't happened that we would still know Elizabeth Oakesmith today in the same way that we know Susan B. Anthony or Elizabeth Cady Stanton. She was that prominent in early feminism.

When she was 16 years old, she married an older man named Seba Smith. Now, Seba Smith is famous because he created a fictional character named Jack Downing, a fictional advisor to Andrew Jackson. And it didn't matter if you were a Democrat or a Whig, everyone in the 1830s and 40s loved him. So Lincoln loved him and Lincoln's primary opponent, Stephen Douglas, loved him. Andrew Jackson loved him and his primary political opponent, Henry Clay, loved him.

Everybody loved Jack Downing. Now, even though Appleton Oakesmith loved to write and loved to read and learned four languages and were raised by these very educated people, his heart and his passion was with the ocean. And so when he was 16 years old, he traveled to China. Then in the 1840s, he went around the coast of South America to San Francisco during the gold rush. He thought that he would spend his time in San Francisco. He was really captivated by the city, but there was a tremendous amount of crime and arson.

The city was burned down several times and there was really no law and order. He was so put off by the crime and the violence and the arson that he decided to leave San Francisco. He acquired a ship called the Mary Adeline and he took on passengers in San Francisco and he went back along the coast of South America. And as he went, he took the passengers and dropped them off in different places. And along the way, he was looking for a cargo that he could take back to New York, which is where his family was living at this time. But he was never able to find a cargo that would take him to New York. And instead, when he got to Rio de Janeiro, he got a cargo that was bound for the west coast of Africa.

And this is where he's going to begin to make international headlines. He loaded the cargo in Rio. He went across the Atlantic Ocean. He made it to the Congo River. And when he got there, a British warship came up alongside of him and under international law in 1852, an American sailor did not have to let a British sailor onto his ship to search for evidence of slave trading. But he let them on anyway.

They would have known what to look for and they likely did not see any evidence of slave trading. They then depart and Appleton takes the Mary Adeline onto the Congo River. And the current of the Congo River is very powerful and it forces things way out to sea. And he winds up getting beached along the shoreline. And as he's stuck there, three thousand African warriors assemble on the coast and they begin to attack his ship. Ultimately, the only thing that saves him are these British warships that had already searched his vessel. They go on board. They unload the cargo so that his ship becomes lighter.

He becomes free and wind up saving his life. Now, we don't know whether Appleton was on a slaving voyage on this ship. Clearly the Africans on the coastline believed he was. My thought is that if Appleton was on a slave trading voyage, he likely was not yet fully aware of what he was embarking on. That the Portuguese who were aboard his ship and that he would be meeting with to discharge the cargo may have had that in mind. And they may not have let him know yet.

He never wrote about it at any rate. But this incident, which becomes known as the Battle of the Congo, makes international headlines. Newspapers throughout the Atlantic world are reporting on what Appleton-Oaksmith had been engaged in. Appleton eventually makes it back. He moves in with his parents and he loses a bundle of money.

Appleton-Oaksmith is essentially flat broke. So he winds up going into business with a fish oil factory owner on Long Island. Now, there's a couple of really big moments that are taking place at this time when he's getting into the fish oil business. One is that secession has come. Oaksmith tries to work with the Tammany Hall political machine in New York City to put on pro-union rallies in New York to rally the nation not to divide. He reaches out to William Seward, the senator from New York, and calls on Seward to come speak to Tammany Hall Democrats.

But he asks Seward to make statements that would be pro-slavery and Seward just ignores him. The other big thing that takes place is that in 1859, petroleum has been discovered. The whaling industry completely bottoms out. Appleton is working with this fish oil factory owner on Long Island and he and his co-businessmen decide we need whale oil for the fish oil factory. Appleton purchases a whale oil boat, but the people who sell it to him think that it doesn't seem kosher. And so they sell him the boat and then they go immediately to Lincoln's U.S.

Marshal. And they say this guy, Appleton Oaksmith, has bought a ship and he says it's for whaling, but we don't believe him. They seize the ship, they seize the cargo that's on it, and decide that they are going to arrest Appleton Oaksmith. Now, they're not yet certain that they can get him for slave trading, but they have a loophole that has come about because of the Civil War.

In 1861, Abraham Lincoln suspended the privilege of the writ of habeas corpus and he did it initially along the east coast and he expanded it to include the area between Washington, D.C. and New York City. And Appleton Oaksmith is in New York City. And so they use Lincoln's suspension of the writ of habeas corpus to arrest Appleton Oaksmith and basically charge him with disloyalty. But they worry that they might not be able to get a conviction in New York. Maybe there's too many people with southern sympathies in New York and that he'll get either a hung jury or an acquittal, but they've got another out.

And that is that Appleton is suspected of buying whaling vessels in New Bedford, Massachusetts, as well. They transfer him up to Boston Harbor and they hold him in a military prison there. And they hold him there until they can prepare to transfer him over to civil authorities in Boston.

Appleton doesn't know what's coming. And one day in January of 1861, an order comes for his release. And he's relieved. He thinks he's going to go free.

Instead, when he walks out, there is the U.S. Marshal in Boston waiting for him. They re-arrest him, this time under civil authority. And they charge him with outfitting ships for the slave trade. They couldn't charge him with slave trading. He wasn't caught red-handed. But they did believe that he was buying these vessels and setting them up to go on a slaving voyage. And the trial is almost a farce.

It's one of the most ridiculous things you could ever imagine. Appleton's defense, his lawyer's defense, was to get about 13 women and girls to look really pretty and sweet and to sit them next to him in the courtroom. And hopefully that would win over the sympathies of the jury. At one point, Appleton's sister-in-law was testifying from the stand.

And I think they planned this in advance because she passes out. And Appleton gets up from the defense table and runs and catches her before she hits the ground. And the jury apparently was taken by the sort of Victorian sentimentalized scene, but not taken enough to acquit him. He's ultimately found guilty. And he goes back to jail. And while he's awaiting sentencing, he somehow escapes and makes his way to Havana.

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Get started at GoDaddy.com. Terms apply. And we return to our American stories and with the story of Appleton Oakesmith. When we last left off, Oakesmith had escaped from prison after getting sent there for buying whale ships during the Civil War. This was well after oil was discovered in Pennsylvania, which struck many people and the Lincoln administration as a thinly veiled attempt to illegally import slaves from Africa. Let's get back into the story. Here again is Jonathan W. White. For the next two years, Appleton will work as a Confederate blockade runner.

And he writes poetry that gets published in Confederate newspapers that sings the praises of the Confederacy. Now, the federal government still wants to get him back. They're trying to come up with a way to do it. The problem is there's no extradition treaty between the United States and Spain. So they can't just go to the Spanish government and say, we want you to arrest Oakesmith and send him back.

But something fortuitous happens for the federal government. A Cuban slave trader named Jose Agustin Arguelles escapes from Cuba and makes his way to Manhattan. And so now in the summer of 1864, you have a situation where an American convicted slave trader is hiding out in Cuba and a Cuban slave trader is hiding out in Manhattan. And so the Spanish minister in Washington, D.C. and Secretary of State William Seward get together and they come up with a plan. You kidnap our guy, we'll kidnap your guy, and we'll swap. We may not have an extradition treaty, but that's okay. This is how we're going to get it done.

And so they agree to do that. And so Robert Murray, the U.S. Marshal in New York City, finds Arguelles, arrests him, sends him back to Cuba, and Arguelles gets 19 years at hard labor for his crime of slave trading.

The Cuban police are not quite as on the ball as the U.S. Marshal was. They go to the home of Sidney Oaksmith, Appleton's brother, get there sometime between 11 p.m. and midnight, and they surround the house. There's about 12 or 13 of them, and three of them go into the house, and they go through the house until they get into a bedroom where they find a man asleep, and they wake him up. And the man says, who are you? And they essentially say, we're not going to tell you, but we're arresting you.

You're coming with us. And so they force this very sick man out of bed, bring him to the front of the house, and then they take him outside. And they then begin to wonder if they've got the right man. They go in, and they ask a servant, do you have a photograph of Appleton Oaksmith? And the servant goes into another room and gets a photograph of Appleton Oaksmith and brings it to the Cuban police, and they look at it, and they realize they've got the wrong guy. They had arrested Appleton's brother Sidney, who really was sick.

This moment made international news. It's getting reported throughout the United States and other places in the newspapers that the federal government had tried to do this sort of illegal kidnapping scheme with the Spanish government in order to capture Appleton Oaksmith. This became a campaign issue in 1864. The Democrats tried to hit Lincoln for acting illegally here. The radicals who broke away from the Republican Party in 1864, led by John C. Fremont, they tried to hit Lincoln for this. And it actually led to a great deal of consternation in Lincoln's cabinet.

Lincoln's attorney general was a man named Edward Bates. He said that Seward was led to this hazardous measure by Seward's belief that it would be a capital hit to win the favor of the extreme anti-slavery men. In other words, Seward was just trying to become popular with the abolitionists. Gideon Wells, Lincoln's Secretary of the Navy, wrote in his diary, he said, constitutional limitations to Seward are unnecessary restraints.

Could the abduction by any possibility be popular? Mr. Seward would do it. William Seward saw what he was doing as perfectly justifiable. Slave trading is one of the most heinous crimes that human beings have ever been involved in and could ever be involved in. And so from Seward's perspective, you needed to do what you needed to do to stop slave trading. He said a nation is never bound to furnish asylum to dangerous criminals who are offenders against the human race. In other words, slave traders, they don't get the sort of protection that other accused criminals might get. And Seward said this was a mere act of comedy between nations. These were two nations who had these offenders against human rights and as an act of comedy or working together, we are going to trade them.

This was perfectly justifiable. Lincoln didn't say anything about this until after his reelection. He said, for myself, I have no doubt of the power and duty of the executive under the law of nations to exclude enemies of the human race from an asylum in the United States. In other words, if you're a slave trader, you are an enemy of the human race.

You don't get the same kind of protections that other criminals might get. Appleton Oakesmith stayed on the lam until 1872. He made it up to Canada. And one thing I didn't mention, I've got a lot on in the book, I mentioned his wife. She tried to help him get out of jail by writing to Lincoln, pleading on his behalf. Well, they had a very tumultuous marriage and a very unhappy marriage. They'd known each other for 10 days before getting married and Appleton decided he wanted to divorce her.

But he didn't tell her. Instead, he used the state of Indiana. Indiana in the 1850s and 60s had very lax divorce laws and you could essentially get a mail order divorce. And the newspapers in New York City during the Civil War would advertise lawyers saying, if you need a quick and easy divorce, hire us.

We'll get you a divorce from Indiana. And so somehow, Appleton hired a lawyer, got a divorce from Indiana, even though he'd never lived there. And he married his cousin. He then took his new wife and kids to London and summoned his ex-wife, who doesn't yet know she's his ex-wife, to come to London. She believes she's coming to London to be reunited with her husband. And instead, he confronts her with divorce papers and says, I'm remarried, sign these.

If you don't, you'll never see your kids again. She feels completely stuck and does this. Meanwhile, Appleton's mother is still pleading with the federal government to pardon her son. And Andrew Johnson is on the verge of pardoning Oakesmith when the ex-wife finds out. And she rushes to the White House, meets with Andrew Johnson, says, my ex-husband's a scoundrel, don't pardon him. And it's an incredible irony that Andrew Johnson, the president who pardoned every ex-Confederate, refuses to pardon Appleton Oakesmith. Oakesmith remains in exile until 1872, when he finally gets Ulysses S. Grant to issue a pardon.

In 1872, Appleton Oakesmith moves to North Carolina kind of on a whim. And in one of these really interesting twists in history that I don't fully know how to explain, he gets elected in an ex-Confederate state as a pro-black civil rights anti-clan candidate. And he actually advocates for black civil and political rights in the state legislature, not full black equality, but for black political rights and for civil rights. And it's a pretty remarkable transformation to see him going from being pro-slavery in the 1850s and 1860s to being convicted of outfitting ships for the slave trade to becoming a pro-Confederate blockade runner and then to becoming a pro-black civil rights politician. And a terrific job on the production, editing and storytelling by our own Monty Montgomery and a special thanks to Jonathan W. White. He's the author of Shipwrecked, a true Civil War story of mutinies, jailbreaks, blockade running and the slave trade. And a special thanks to the U.S. National Archives for allowing us to use this audio.

Originally a part of a lecture given by White. And what a story he told. Forget the Cuban Missile Crisis. Long before that debacle, we had the crisis of the exchange hostages kidnapping plot. And this guy comes out not only unscathed and pardoned, but ends up running for the State House on the platform of pro-civil rights for former slaves in the state of North Carolina. The story of one of the Civil War's great grifters and perhaps a redeemed one.

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