The Friends of Rocheport Historical Society added a new name to its Hall of Fame this June: Robert Alexander Caskie, a Scottish-born tobacco and banking businessman who spent his final years in our town — and whose life, it turns out, may not have ended the way the record books say.
Caskie’s story starts well before Rocheport. He married Amanda Gregory, daughter of Missouri Governor John Munford Gregory, and served as a colonel in the Confederate Army under General Robert E. Lee during the Civil War. According to a recent piece by Columbia Missourian columnist Timothy Carson, Caskie was assigned to guard abolitionist John Brown after the raid on Harpers Ferry and witnessed his execution in Charleston. He later became friends with John Wilkes Booth, who served as his quartermaster.
After the war, Caskie moved to Rocheport to revive his family’s tobacco business — which is how he ended up on our stretch of the river, and now in the Historical Society’s Hall of Fame.
Here’s where the story gets strange. Caskie reportedly drowned in the Mississippi River, and his family listed him as officially deceased in 1902. Carson’s reporting notes that before his death, Caskie had abandoned his wife and children in St. Louis — the kind of detail that tends to invite questions.
Carson’s column draws a line from Caskie to a very different figure: Roland Smythe, known as the “Hermit of the Wabash,” a reclusive naturalist and poet who lived alone in a cabin above the Wabash River in New Harmony, Indiana, for more than 23 years. When Smythe died, his remains were eventually moved to Hollywood Cemetery in Richmond, Virginia — buried beside a woman named Amanda Gregory Caskie.
That name next to the hermit’s grave is the thread Carson pulls on. His column raises the possibility that Caskie faked his own drowning and spent his later years as Smythe, trading one identity — and one set of debts and obligations — for a quieter life on a different river. To be clear, this is Carson’s exploration of the record, not a settled fact; there’s no document that definitively places Caskie inside Smythe’s cabin. But the coincidence is enough to have Rocheport history buffs talking, and it’s easy to see why: reinvention, a second chance, walking away from one life to start another — themes that don’t feel especially distant from a small river town that has reinvented itself more than once.
The Historical Society’s Hall of Fame induction was in June; Carson’s column ran in the Missourian on August 12. Whether or not Caskie really became the Hermit of the Wabash, his documented life alone — colonel, John Brown’s guard, Booth’s friend, Rocheport tobacco man — is enough to earn the plaque.
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