America's Greatest Grifter? The Odd Story of Appleton Oaksmith: Presumed Slave Trader, Confederate Spy, and Voting Rights Activist
Our American Stories
iHeartPodcasts
4.6 • 817 Ratings
🗓️ 30 January 2026
⏱️ 20 minutes
🧾️ Download transcript
Summary
On this episode of Our American Stories, they say the apple doesn’t fall far from the tree—but Appleton Oaksmith landed on another planet. His mother was a feminist who knew top abolitionists; his father, a cartoonist admired across party lines. Appleton? He was hunted internationally for presumed slave trading and a failed kidnapping in Cuba that may have threatened Lincoln’s reelection. Yet he later fought for Black voting rights. Jonathan W. White, author of Shipwrecked, shares the story—courtesy of the U.S. National Archives.
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Transcript
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| 0:00.0 | This is an I-Heart podcast. |
| 0:02.6 | Guaranteed human. |
| 0:14.0 | And we return to our American stories. |
| 0:17.3 | Up next, the story about a man born into a life of privilege in Maine who took to the sea and led the U.S. on a wild goose chase that became a political crisis of sorts in 1864. |
| 0:29.9 | You're to tell the story of Appleton Oaksmith is Jonathan W. White. Let's get into it. |
| 0:35.4 | Appleton Oaksmith's mother was a woman named Elizabeth Oaksmith, and she was a very |
| 0:40.4 | prominent first-wave feminist. She was a lecturer, an essayist, a poet, a playwright, a |
| 0:46.6 | journalist. She traveled in literary circles. She was friends with Edgar Allan Poe, |
| 0:51.9 | Henry Wasworth Longfellow, Horace Greeley. |
| 0:54.6 | She would speak on behalf of women's rights, but she was also in favor of ending slavery. |
| 1:01.6 | 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. |
| 1:10.4 | She either thought the last name Smith was too boring or |
| 1:13.9 | she didn't want her kids to have her husband's surname. She went by Elizabeth and then her |
| 1:20.0 | middle name, Oakes, and then her husband's last name Smith. Her son's last name is Oakesmith as |
| 1:26.2 | one word without it, the E.S. It's just kind of smushed together. |
| 1:30.1 | I am convinced that if the story hadn't happened, that we would still know Elizabeth Oaksmith today |
| 1:36.0 | in the same way that we know Susan B. Anthony or Elizabeth Cady Stanton. She was that prominent |
| 1:41.5 | in early feminism. When she was 16 years old, she married an older man named |
| 1:47.5 | Siba Smith. Now, Siba Smith is famous because he created a fictional character named Jack Downing, |
| 1:55.1 | 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 |
| 2:04.1 | loved him. So Lincoln loved him, and Lincoln's primary opponent, Stephen Douglas, loved him. |
| 2:09.9 | Andrew Jackson loved him, and his primary political opponent, Henry Clay, loved him. Everybody |
... |
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