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Part 6 — O.R. Singleton

Updated: Apr 6, 2022

There are several men in the periphery of Robert Jefferson’s story. These include Thomas Jefferson Catchings, M.D., who had owned Robert’s wife, Celia, and probably their daughters, Lucy and Georgiana. Then there was Thomas’ brother, Silas Mercer Catchings, also a slave-owning planter. (I think it’s ironic that they are referred to as planters, when they surely never did any of the planting. Just sayin’.)

And, of course, there were the executors of John Thomas Dearing’s will; S.D. Livingston, who in 1833 was serving as the clerk of the Madison County, Mississippi, Circuit Court, and a business partner, Jesse Heard.

There is also Otho Robards “O.R.” Singleton. Born near Nicholasville, Kentucky (just south of Lexington), on 14 October 1814, according to Wikipedia, he attended common schools and graduated from St. Joseph’s College in Bardstown, Kentucky. (I have been to that college, where I interviewed a priest for an article I was writing several years ago.)

Singleton’s profile on Wikipedia states that he later graduated from the University of Lexington; however, I’m not sure which university they are referring to; I can find no university of that name – in the 1800s or today. It couldn’t be the University of Kentucky (sorry, Wildcats); UK was established in 1865, long after Singleton left to find his fortune in Mississippi.It may have been Transylvania University, also in Lexin, which was established in 1799. This is likely where he studied, as I found this today on Transylvania's website:

So, I just found this on the Transylvania University website's history page:

Transylvania’s Law Department becomes one of the most distinguished in the nation as a result of George Robertson, Chief Justice of the Kentucky Court of Appeals, joining the faculty. It and the Medical Department graduate a number of notable Americans in the pre-Civil War era, including future justices of the United States Supreme Court, Samuel Freeman Miller and John Marshall Harlan (pictured).

So, most likely, that's where O.R. Singleton studied while in Lexington.

By 1838, Singleton had moved to Mississippi and was admitted to the bar in Canton. He first served in the state House of Representatives in 1846-47, then served as a state senator from 1848 to 1852 – 1852 being the year he signed Robert Jefferson’s freedom papers, as mentioned in the 1879 Indianapolis Journal article.

Singleton served Mississippi's 3rd Congressional District as a Democrat* in the U.S. House of Representatives from 1853 to 1855. He lost his bid for re-election, but was elected to represent the state's 4th Congressional district from 1857 to 1861, when he withdrew from that post to represent Mississippi in the First and Second Confederate Congress. Despite his pro-secessionist stance, Singleton was returned to the U.S. House of Representatives in 1875 and served there until 1887. He died in Washington, D.C., on 11 January 1889, and was buried in Canton Cemetery back in Mississippi.

A history professor at University of Mississippi, “Ole Miss,” told me that Singleton had emancipated only one or two enslaved African Americans. "He kept so many others enslaved … fought to defend slavery, and then after the Civil War, fought to uphold white supremacy.” She was not a fan of O.R. Singleton, nor am I. In a reply email, I clarified that my interest in Singleton was because my Robert Jefferson was one of the enslaved for whom he had signed emancipation papers; Mississippi law at that time required the papers to be signed by a state representative. This time, her response was "Wow!"

Clearly, Singleton was not someone who had any particular love for the black man. So why would someone so rooted within the institution of American slavery — and a staunch believer in the ideology of white supremacy — have seen fit to emancipate Robert Jefferson, his wife Celia, and their daughters, Lucy and Georgiana? Well, aside from the fact that the man who owned them was going to receive a small fortune ($4,600, or about $130,000 today) in the deal.

This all seems to go back to the question of who owned Robert after John Thomas died. It may have been Silas Catchings, who is mentioned in a newspaper ad with Dearing before Dearing’s death. But, Silas met an unfortunate end. Allegedly, one of his enslaved men identified only as William, under the cover of night, slipped to Silas’ house, found his bedroom window, lifted it and shot him dead in his sleep on Christmas Day 1849.

It would make sense that Silas may have been Robert’s owner at the time of his demise; Robert had lobbied for his freedom but was denied it by whomever owned him after John Thomas died ten years earlier. If that's the case, it would make sense that Robert would then have been transferred to Thomas, who already owned the rest of Robert’s family. Robert only talks about making arrangements with one man to purchase their freedom, and he would have been living on Thomas' plantation for only a year or so when he was given the opportunity to work for his own money – money that, eventually, would go back to the slave owner, anyway, by July 1852, when Singleton signed the Jefferson family's emancipation papers.

Additionally, Robert was well-thought of, not just by the Catchings (as noted in the quote below), but his papers bore the signatures of 150 Canton citizens, according to Robert.

“The nurse of Nannie and Thomas C. Catchings, when infants, was ‘Aunt Celia,’ a very accomplished and capable servant; high-toned, reliable and almost white. Her husband, Robert Jefferson, was a freed man, and a carpenter: a courteous negro from Virginia, once owned by President Thos. Jefferson. He bought her and her children for a trifle, and moved to Indianapolis, Indiana, about 1848. Their children were named Mississippi and Lucy.”

Nannie Clendinen Catchings Baird, Dr. Catchings' daughter, wrote this in a family genealogy that included her own reminicences, "The Clendinen, Myers and Mills Families," published in 1923. I would love to know, if $130,000 in today's money is what she consideres merely a "trifle," what she considered to be a fortune.

While Nannie had a few of the details wrong — President Thomas Jefferson never owned Robert, but she clearly recalled there was a connection — it helps the timeline. It makes far more sense for Dr. Catchings to have taken Robert from Silas' estate, than t had Robert been purchased from J.T. Dearings' estate by his business partners Heard or Livingston.

As always, more research is needed. My hope is to find a repository that still holds the papers of O.R. Singleton, J.T. Dearing, Dr. Catchings and maybe Jesse Heard. Perhaps somewhere in those papers the full story can be found.

* Note: Democrats in those day were the conservative party; they and the Whig Party were, for the most part, unabashedly pro-slavery.

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