Theodore Middleton was different than Alexander Lawson Smith and Archibald Golder (link when published on June 7). By 1781, he was a 23-year-old man, born in Charles County, Maryland, the son of Mary Hawkins and Smith Middleton. He had been, like the others mentioned, an officer in the Extra Regiment, but, different from them, a mid-level officer, who was promoted while others resigned their ranks.
Theodore was, when he joined the Extra Regiment, living in Prince George’s County, Maryland, where he would live until at least the 1830s. While the record of his age was lost or destroyed, he remembered when applying for his federal veterans pension, that he was a “commissioned Officer” who performed “three Tours of survice” and was acquainted with Col Luke Marbury, also from the same county, commanding a “Regiment at the battle of Jermons town” or Germantown in Pennsylvania where he was taken prisoner. He also recalled that he was acquainted with Col. John Hoskins Stone and Col. Uriah Forrest, both of whom were wounded in the battle just mentioned, along with a person named General Francis Nash, who was killed at the same battle.He also remembered that he did receive a “commission from the Governor and Council of Maryland,” but it had been “lost or mislaid” by the 1830s. 
As one of the 19 within the Extra Regiment with a pension, what he has to say is further worth noting. In applying for his pension in February 1833, he noted that he entered the Maryland Line in April 1779 as a Lieutenant and later served in the Extra Regiment with Captain Mountjoy Bayly, Major Edward Giles [link when published on June 21], Alexander Smith, and Nathanael Greene. He also recalled that he marched with the regiment
from Annapolis to Philad’a where he remained two months. From there a short time he took shipping at the head of Elk River and came to Annapolis in the State of Maryland where he staid for some considerable time. This tour of service embraced fourteen months. He then marched from Annapolis to Alexandria, Fredg. [Fredericksburg] Richmond and Petersburg Virginia, Crossed over into the State of North Carolina, and was at the battle of Guilford C. H. in said state, March 1781 [Guilford Courthouse, 15 Mar 1781]
He then said that after that point, with the end of a “Southern tour of sixteen months” he returned to Maryland in October 1781 “as a Supermerary
officer by General Green” during which time he was commissioned immediately as a Captain. At that point hewas commanded by Col. Uriah Forrest to go to Annapolis, where he stayed a recruiting officer for nine months, until he was “discharged by Col. U. Forest.” While this story has some truth to it, the fact is that he started as a Second Lieutenant, would help organize the specifics of a company within the Extra Regiment. He would later be paid as part of the “late Extra Regiment” in March and April of 1781, and be appointed “Capt. Lieutt of a Company of Foot to serve in this State for one year” the same month. He would write Governor Thomas Sim Lee in September 1781, noting about gathering infantry to organize a defense of the Chesapeake Bay region:
As a considerable time has elapsed since I had the Honor of hearing from you, concerning the raising the compy of infantry for the defence of the Bay, I should be glad to know if you still propose that corps to be raised, If not, I must Sollicit your Excellency In an apointment in the first com.[company] that may be recruited.
While the information on Theodore is not as wide-spread as other officers, there is still a story worth telling.
Beyond the pension
Scattered sources about Theodore do tell some parts of a story. On November 20, 1789, in Upper Marlborough, he married a woman named Julia/Juliana Huxton, and the following year he headed a household with two males under age 16, one female (Julia), and seven enslaved blacks.  With Julia he would have, ultimately, eight children. They would be named Sarah, Henry O., Theodore, Walter, Chloe Ann, Mary H. Charles S, and Susan.
Also in 1789, he was named as executor of Dr. Edward Semmes estate, possibly because of the close relationship between the two men. By April 1791 he was cited for not passing a final account on the estate but was allowed to sell a portion of the estate to meet the debts of Dr. Semmes. 
In later years, Theodore would still own enslaved blacks. In December 26, 1799, a woman named Ann would be described as “natural daughter of Margis, slave,property of Theodore Middleton living in Prince George’s County.”
By 1800, would be living in “formerly part of Prince Georges MD, Washington, District of Columbia, United States,” but possibly didn’t move into the district, but rather where he was living became part of the federal capital. Three white males under age 10, one white male over age 45 (himself), two white females under age 10, and one white female under age 45 (his wife) would be living in the household. Of course, he would also own 15 enslaved blacks, more than anyone on either one of the corresponding census pages. The latter implies that he had a plantation of some type, although the location of this land is not known. Despite this mention of living in Washington, D.C., he would be noted as a resident in Prince George’s County through a number of land records, perhaps indicating that the area he lived was near the border line.
Twelve years later, in August 1812, Theodore would mortgage three enslaved black men to a man named Robert Bench. They would be: Joe, age 23, Daniel, age 21, Leonard, age 40, and Jim, age 15.  This business of mortgaging enslaved blacks, a “rent-a-slave industry” was a moneymaker for slaveowners, not only showing that “the legal treatment of slaves as property in the South” (the same goes for deeds of enslaved black people) but was, at the time, used to “solve” issues of ownership over such peoples. Furthermore, the acquisition of more enslaved blacks could be “financed by mortgages” with bonds sold to investors based on “value of those mortgages” leading to securities. The latter were “based on enslaved human beings” to create a “bubble” of such assets, leading to speculation which was like that on “home mortgage derivatives that helped cause the financial crisis of 2008” as some writers have pointed out. Even Thomas Jefferson (as did others) mortgaged his enslaved blacks, which was one of “rescues” the Jefferson family had “from a bad harvest,” keeping the “family afloat while a new and grander version of Monticello took shape” as Henry Wiencek writes in Master of the Mountain: Thomas Jefferson and His Slaves.
This mortgage between Theodore and Bench was a bit ahead of the curve since widespread mortgaging would not occur until the 1830s. Historical scholar Edward Baptist explains this and how US finance grew on the back on enslaved labor in increasing intensity in the 19th century:
In the 1830s, powerful Southern slaveowners wanted to import capital into their states so they could buy more slaves. They came up with a new, two-part idea: mortgaging slaves; and then turning the mortgages into bonds that could be marketed all over the world. First, American planters organized new banks, usually in new states like Mississippi and Louisiana. Drawing up lists of slaves for collateral, the planters then mortgaged them to the banks they had created, enabling themselves to buy additional slaves to expand cotton production. To provide capital for those loans, the banks sold bonds to investors from around the globe — London, New York, Amsterdam, Paris. The bond buyers, many of whom lived in countries where slavery was illegal, didn’t own individual slaves — just bonds backed by their value. Planters’ mortgage payments paid the interest and the principle on these bond payments. Enslaved human beings had been, in modern financial lingo, “securitized.” As slave-backed mortgages became paper bonds, everybody profited — except, obviously, enslaved African Americans whose forced labor repaid owners’ mortgages. But investors owed a piece of slave-earned income. Older slave states such as Maryland and Virginia sold slaves to the new cotton states, at securitization-inflated prices, resulting in slave asset bubble. Cotton factor firms like the now-defunct Lehman Brothers — founded in Alabama — became wildly successful. Lehman moved to Wall Street, and for all these firms, every transaction in slave-earned money flowing in and out of the U.S. earned Wall Street firms a fee. The infant American financial industry nourished itself on profits taken from financing slave traders, cotton brokers and underwriting slave-backed bonds. But though slavery ended in 1865, in the years after the Civil War, black entrepreneurs would find themselves excluded from a financial system originally built on their bodies.
While what Baptist is saying is admittedly controversial to some, he helps put the mortgage between Theodore and Bench into context.
In later years, he would give away land for almost nothing. In 1814, two years after the previously mentioned mortgage, he would be one of five commissioners (the others named Josiah Moore, Thomas Bunch, James Beall Senior, and James Bealle Junior) who had gained lands after the death of Ignatius Handy in 1811. However, the courts said the lands should be divided without loss and injury to all parties, and the son of Ignatius, in 1812, received land, but not the commissioners so they advertised the real estate for sale and it was bought by Mordecai Ridgeway.  Perhaps due to legal wrangling they sold all of the estate to him, including numerous parcels of land such as Friendship’s Addition, Crichet Bat, and Lanhams Delight. By almost nothing I mean that they only received $5.00 from Ridgeway. This could be because all of the commissioners were good friends of his or that they wanted to be rid of the land and didn’t care what it sold for. Whatever the reason, Middleton was involved in the middle of it.
The mid-1810s and into the 1820s
By 1815, Theodore was buying and selling land with relatively large price tags, possibly showing his wealth. That year, he paid a man named Stanislaus Hoxton $2,176 dollars for two tracts which were named “Triall” and “Deer Pond Enlarged.”  This wasn’t the end of the story for those land tracts. In 1820, his son, Henry O. paid him $50 dollars for “10 parcels” of a land, which were part of the two above mentioned tracts.  The same year, George Semmes would pay him for these two tracts. He would pay $2,000.  Six years later, the tracts were sold again. Likely because of his role as an administrator of Semmes estate, he had regained ownership over the land, and sold it for $2,000 to a woman named Sarah Folson of the same county. 
Some may say that Theodore lost money in these land dealings. After all, there was a negative 3.93% average inflation rate between 1815 and 1826, as noted by Measuring Worth, meaning that the relative value of the $2,176, which had had paid for the land, was now $1,400. Hence, you could take from this, he had a money loss, with his land worth less. However, he still gained, even when you factor in the lower relative value, he brought in $3,690 for the varied land sales in 1820 and 1826.  Hence, he garnered, approximately, a 69.6% profit from the transaction as a whole. This land dealing was noting new. Some his ancestors within the county had sold numerous tracts of land to willing buyers. 
In 1820, two men, Francis John Lobson and George Semmes, would buy $3,000 dollars worth of “goods” from Theodore.  He would grant them 12 enslaved blacks named Daniel, Phil, George, Lewis, John, Sam, Grace, Betty, Celey, Eliza, Grispey?, and Margarett. He would also give them the following:
“five head of horses, nine head of cattle, twelve head of hogs, thirty two head of sheep, and all the household and kitchen furniture which at this time belongs to me the said Theodore Middleton”
While the average price of enslaved blacks was definitely not $900.00 (if it was, they would have been paying $10,800 dollars) as it was in New Orleans at this time, they undoubtedly figured into his transactions.  Those involved in the transaction probably did not consider the dehumanizing effects of enslaved blacks being sold alongside livestock, only considering them another form of “property” as part of their wheeling and dealings.
Selling and buying of enslaved people ran in the Middleton family. His son, called Theodore Middleton, Jr. in land records, while he is called Theodore Middleton, Sr.,would pay General Semmes and Francis Tolson for a “young negro man named Sandy.”  One of his ancestors, Thomas Middleton Sr. of Piscataway, Prince George’s County, was a major player in the business as well. In February 1743, he sold an enslaved black woman named Lucy to John Lawrence for several thousand pounds, while the following year he would be paid four thousand pounds of tobacco for two enslaved blacks by James Gibbs. The first individual, a woman named Judith, he would pay three thousand pounds of tobacco, while the second was a man named Henry for which he would pay 1,000 pounds of tobacco.  Such tobacco not only determined a “man’s wealth” but it was a principal source of revenue for the colonial governments of Virginia and Maryland. After 1730, Marylanders became aware that Virginia’s inspection system gave the state “a great advantage over Maryland by raising the quality and reputation of its’ tobacco” so in 1747 the Maryland General Assembly “passed the Maryland Inspection Acts which remained a permanent feature of the trade in Maryland.” By the time Thomas engaged in this transaction, the price of tobacco has stabilized, avoiding wild price fluctuations that has been a feature in the past within the Chesapeake Bay region.
Jumping forward to the 1830s
In 1832, a Virginia man named Erasmus Gantt noted he served with Middleton in the spring of 1782, including on the Potomac River, ending his military service in Annapolis.  All that is known beyond this is that he was part of the defense of the Chesapeake Bay, and would appointed a Lieutenant.
The same year as Erasmus submitted his pension, another man named John Boone, of Charles County, a Lieutenant in the First Maryland Regiment would also mention Theodore.  In the pension, which would continue after his death, sometime before 1853, by his wife Mary Laud, it would note he served from May 1776 to October 1781, fought at the battle of Yorktown, still had his discharge certificate. Even with all of that, Theodore is mentioned only in passing, deep inside the pension:
The same would seem, from a simple search, to be the case in the pension Henry Hill filed by Hester Hill, his wife. Apart from being a captain, Henry, who lived in D.C. in the 1830s, he would serve from 1777-1782, throughout the Revolutionary war, and be a native of Prince George’s County.  Unlike Boone’s pension, in 1841, Theodore would personally attest that Henry was a captain, commanding a company of Maryland militia at the Battle of Germantown (1777):
In 1838, five years after Captain Bayly, in Washington City attested to the fact that he and Benjamin Murdoch were part of the Extra Regiment, he would petition the US House of Representatives for relief.  In his petition, he would note his service as a lieutenant in the Extra Regiment, wanting five years pay for his service, and he would receive such pay accordingly.
Into the 1840s
By 1840, Theodore would still be living in D.C. while his son lived in Baltimore. Within the household would be two white males, one under age 5, the other between ages 30 and 40, and two white females, one between ages 5 and 10, the other between ages 20 and 30. With these individuals were undoubtedly his children, would be two enslaved blacks, one whom was a male between ages 5-10 and the other also a male but between ages 20 and 30. There would also be one “free” black woman living in the household between ages 10 and 24.
There a few other facts which are known about his life.  The Theodore’s wife, Julia, owned varying enslaved blacks and was well-off, to an extent, before her death in November 1842. When she died, eight children were left with only Theodore living until his death.
In terms of Theodore’s death, some sources seem to indicate that he died 85 years of age on January 28, 1844, Theodore died in Prince George’s County, but still within the bounds of Washington, D.C. seemingly. Others seem to think that he died in 1845 for some reason.  As it turns out, those that said he died in 1844 would be correct, as proved by the short death notice in the Baltimore Sun:
It would be at this point that the Baltimore Republican & Daily Argus would call him “a character for probity and honor” from what we know. Other requests of the exact copy of the newspaper would be required to verify this quote, specifically from these institutions.
After his death
Hence, after his death, his heirs began to collect his pension benefits from the Federal government. Many of his descendants, including his son, had the same name, owning property in Prince George’s County which included a house of some kind. Also there are reports that his son Theodore served as a traveling agent in Baltimore for the Maryland State Colonization Society and possible mentions of him in within Daniel Boone Lloyd’s genealogy titled The Middletons and kindred families of southern Maryland.  Later, one of his descendants, James Middleton, would serve as a Confederate soldier while another would be sheriff in Harlon County, Kentucky in the early 20th century as numerous newspapers, ranging from the New York Times to Washington Post would attest.
In all, he would be honored by his family and part of the annals of Maryland history for years to come.
 He also said that in his present living area he was “personally acquainted with the Rev. Spencer Mitchell, George Semmes, Henry A. Callis, Henry Gantt, John Addison, Bazil Hatten, Notley Maddox…Henry Tolson Esqrs…Judge Key, and the Hon’le B. J. Semmes.”
 Henry Wright Newman, “Captain Theodore Middleton” within The Maryland Semmes and Kindred Families (Baltimore: Maryland Historical Society, 1956), 282. Later one of the Middleton family would marry into the Boone family.
 Deed between Theodore Middleton, Josiah Moore, Thomas Bunch, and Mordecai Ridgeway, Oct. 5, 1814, Prince George’s County Court, Land Records, Liber JRM 16, p. 208, 209, 210, 211 [MSA CE 65-45]. Courtesy of mdlandrec.net.
 Originally he was paid $2,050 for such land in 1820, and $2,000 in 1826.
 Bill of sale by Theodore Middleton to Francis John Lobson, April 3, 1820, Prince George’s County Court, Land Records, Liber AB 1, p. 264 [MSA CE 65-48]. Courtesy of mdlandrec.net.
 “Average Price of Slaves, New Orleans, 1804-1862” within Edward Baptist, The Half Has Never Been Told: Slavery and the Making of American Capitalism (New York: Basic Books, 2014), 174, citing the New Orleans Sale Sample, 1805-1862, which was compiled by Robert W. Fogel and Stanley L. Engerman.
 Bill of Sale from Gen. Semmes and Francis Tolson to Theodore Middleton, November 12, 1821, Prince George’s County Court, Land Records, Liber AB 2, p. 33 [MSA CE 65-49]. Courtesy of mdlandrec.net.
 Bill of sale involving Thomas Middleton and John Lawrence, Feb. 24, 1743, Prince George’s County, Land Records, Liber BB 1, p. 85, 86 [MSA CE 65-12]. Courtesy of mdlandrec.net; Bill of sale involving Thomas Middleton and James Gibbs, May 17, 1744, Prince George’s County, Land Records, Liber BB 1, p. 130, 131 [MSA CE 65-12]. Courtesy of mdlandrec.net; Bill of sale involving Thomas Middleton and James Gibbs, May 17, 1744, Prince George’s County, Land Records, Liber BB 1, p. 131, [MSA CE 65-12]. Courtesy of mdlandrec.net.
 Pension of Erasmus Gantt, 1832, Survivor’s Pension Application File, S.10.727, Revolutionary War Pension and Bounty-Land Warrant Application Files, National Archives, NARA M804, Records of the Department of Veterans Affairs, Record Group 15. Courtesy of Ancestry.com and HeritageQuest.
 Pension of John Boone, 1832, Pension Application File, S. 8076, Revolutionary War Pension and Bounty-Land Warrant Application Files, National Archives, NARA M804, Records of the Department of Veterans Affairs, Record Group 15. Courtesy of Ancestry.com and HeritageQuest.
 Pension of Hester Hill for benefits of Henry Hill her husband, 1856, Pension Application File, W. 14,907, Revolutionary War Pension and Bounty-Land Warrant Application Files, National Archives, NARA M804, Records of the Department of Veterans Affairs, Record Group 15. Courtesy of Ancestry.com and HeritageQuest.
 Middleton’s pension “includes a certificate by Mountjoy Bayly of the District of Columbia dated 27 Feb 1833, signed as shown, certifying Middleton’s service in words almost identical to those in the above application. On 11 March 1833 Theodore Middleton applied to have his pension payable in Washington, DC. A note by W. H. Middleton dated 25 Oct 1855 asks that the Commissioner of Pensions allow examination of the papers pertaining to his father, Theodore Middleton.”
 Newman, “Captain Theodore Middleton,” 283.
 “Reports of Traveling Agents,” Maryland Colonization Journal, Baltimore, Dec. 1856, Vol. 8, no. 19, 304. He is reportedly mentioned on pages 97 and 376 at least of Daniel Boone Lloyd’s The Middletons and kindred families of southern Maryland.