Volume 1 Issue 5
May 2001
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John J. Graves
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Willard Gentry

Abstract – A
One family's introduction to their ancestral relatives, two Richards and a Joshua Gentry, and how they profited from it.

In mid-May of 1997, my wife Marilyn suggested that we visit the National Cemetery located at Jefferson Barracks in St. Louis on Memorial Day. She thought it would give our two daughters, Jordan and Alexandra, a better understanding and appreciation of the significance of the holiday. I thought it was a good idea since children today (ours included) largely view the holiday as just another three-day weekend. I knew Marilyn had a soft spot in her heart for veterans - especially those who, like her father, fought in World War II. Since I had never been there, I knew she and I would enjoy the trip even if the girls may not.

When we arrived at Jefferson Barracks late that Memorial Day morning, we were surprised to be met by heavy traffic, especially in light of the weather. The sky was very overcast and it was trying hard to rain though it only managed to sprinkle intermittently. Once inside the cemetery grounds, we quickly realized that there was a Memorial Day Celebration in progress. The affair was widely attended by veterans groups, scout troops, numerous state and local elected officials and dignitaries and the general public not to mention relatives of those buried there. Jefferson Barracks National Cemetery is, I have learned, one of the largest National Cemeteries in the country having over 170,000 buried there. We parked and made our way to a small building that serves as a visitor's center and graves registry. Since we have no family in St. Louis, we ignored the computerized registry and viewed instead the various plaques and displays that decorated the building's walls.

After a bit, I wandered outside onto a porch at the back of the visitor's center and found a desk housing a set of binders containing the names of the thousands buried there. On the desktop, under glass, there were posted several items of interest including some information about a Revolutionary War Veteran buried at Jefferson Barracks - a Private Richard Gentry. The name Gentry sounded familiar to me, as I thought I had heard my grandmother, Amanda Lorene Glascock LaFrance, mention the name when I was a young boy.

On a couple of occasions, I remember my grandmother pressing me into service on what was then called Decoration Day. My job was to cut numerous flowers from my Uncle John's rose garden and wrap them in wet newspaper. Once this was done, I was to escort her to the various gravesites and help her decorate our relatives' graves. Our first stop was always Grandview Burial Cemetery located at the southern edge of Hannibal where we then lived. We'd decorate two graves at Grandview. One belonging to my grandfather, John T. LaFrance who died on the fourth of July and the other belonged to my uncle, Dr. John J. Reichman, for whom I was named and who was, unknowingly, supplying the roses.

From there, we would travel 10 miles south to New London's Barkley Cemetery. More Glascocks reside there than any place on (or in) earth! My grandmother and her sisters would always reminisce about who was related to whom and how they were related - often by multiple paths! I'm sure these conversations were modest in length, though at the time, they seemed to last forever. Or as my daughters would say in a musical way, "bor-ing." It was on one of these occasions that I think I heard the name Gentry mentioned.

I called my wife and daughters out on to the porch to show them what I had found. I told them that we might be related to this Richard Gentry fellow. After obtaining directions to the gravesite located in the Old Post Section of the cemetery, we drove to that area, reparked, and walked through the wet but neatly mowed grass. The Old Post Section at Jefferson Barracks sits atop a bluff overlooking the Mississippi River. We spread out, each walking down a row of headstones. In a short time, we located Richard Gentry but strangely, the date didn't fit that of a Revolutionary War veteran. We continued to look around and found only a few yards away, a second headstone bearing the name of Pvt. Richard Gentry and the inscription "Rev War Vet." We discussed the possibility that these two Richard Gentrys were related to one another or maybe even to us. We made a note of the dates on the headstones thinking we would try to find out who these Gentry fellows were.

Many weeks had passed when I came upon the notes we made that Memorial Day. Unfortunately, all of my immediate relatives on my mother's side of my family were deceased so I decided to call a distant relative, a Henry Glascock in New London hoping he might be able to identify the Gentrys we found at Jefferson Barracks. I recanted the day's events and he told me that there were a couple of books written on our family's history but he didn't know where to get one. He suggested I speak with another New London resident, a Roberta Blackwell assuring me that she was knowledgeable in these matters. A few days later, I reached Mrs. Blackwell on the phone, introduced myself, and again told her our Memorial Day story. She quickly told me that she knew my mother and my grandmother well and informed me that "my grandmother's mama was a Gentry!"

Several months passed before I obtained any written information on my family's history, whereupon on further investigation, I learned that we were indeed related to Richard Gentry - both of them! That evening, I asked my daughters if they cared to guess whom that Richard Gentry, the Revolutionary War veteran buried at Jefferson Barracks Cemetery, was. (They didn't, but I continued.) I told them "he's your great, great, great, great, great (count them - five) grandfather and the other Richard Gentry was their great (times four) uncle!" Much to my dismay, they didn't seem greatly impressed. I did take solace in the fact that my wife appreciated the consequence and I knew the girls would too, in time.

Private Richard Gentry (Sr.), I learned, is one of only two Revolutionary War veterans buried at Jefferson Barracks National Cemetery. He is a well-known early Kentucky pioneer. Richard traveled from Virginia with his wife Jane Harris Gentry and his one-year-old son, Ruben following the Wilderness Trail through the Cumberland Gap to Fort Boonesborough in Madison County, Kentucky in 1786. Jane, pregnant at the time with their second son David (born at Ft. Boonesborough on 11 Feb 1787), rode horseback and carried baby Ruben in her arms. Richard walked leading his other horse loaded with all their worldly possesions. Richard became a very prosperous plantation owner and fathered 19 children, all but one of whom lived well into adulthood. Many of Richard's 15 sons, moved west and, like their father, became prominent Missouri pioneers - especially Colonel Richard Gentry Jr., who is buried at Jefferson Barracks a few paces from his father, and Colonel Joshua Gentry, my great, great, great grandfather.

Editor's Note: Richard was a son of David Gentry, who was born in Louisa County, Virginia and lived in Albemarle County, Virginia before moving to Kentucky. David married Mary Estes and was a son of Nicholas-II Gentry, and grandson of Nicholas-I, the immigrant. Author John Graves' family tree in his private website, needs correcting as it shows Nicholas-II's wife as Mary Brooks (unfortunately a common error), whereas Mary was married to Nicholas' nephew, Nicholas the Younger who was a son of Samuel-II Gentry.]


Born - 25 Aug 1788 - Cabin in the cane break, Madison Co., Kentucky
Died - 25 Dec 1837 - Okeechobee Swamp, Florida

In 1818, Colonel Richard Gentry, Jr., Revolutionary War Richard's third son, founded the town of Smithton, Missouri located in Boone County, Missouri. Three years later, due to a shortage of water, all 20 residents moved across the Flat Branch and Columbia, Missouri was founded. Richard and his wife, Ann Hawkins Gentry, owned and operated Gentry's Tavern which served as a hotel for travelers, a meeting house, and post office. Col. Gentry was a well-known Indian fighter and served as a general in the Black Hawk Indian War. He was a founder of Stephens College in Columbia and following statehood, led the Missouri Volunteers in the Second Seminole Indian War.

The first war with the Seminoles ended badly with the U.S Army accomplishing few of its objectives. Later, in 1830, President Andrew Jackson signed an act which called for the removal of all Indians east of the Mississippi River to the new Indian Territory (Oklahoma). The Seminoles signed treaties agreeing to move in 1836. However, many Seminoles did not want to leave their homeland. One Seminole warrior, Osceola, who fought against General Jackson in the first war, was able to convince many Seminole and Creek Indians to stay and fight. In 1836, Osceola and a band of Seminoles attacked a company of U.S. Army soldiers killing over one hundred with only three escaping the onslaught. This massacre prompted Congress to appropriate more funds and send more troops. It was at this point that Missouri's U.S. Senator, Thomas Hart Benton, told his legislative peers what was needed to solve this problem in Florida was to send in some Missourians as they were accustomed to dealing with the Indians and knew what was required. Congress agreed and in September of 1837, the Secretary of War issued a requisition on Missouri Governor Boggs for the volunteers. Senator Benton called on his old friend Richard Gentry to lead the force into action. It angered the officers in the regular U.S. Army to be forced to accept the help of Missouri's volunteers, especialy in light of their recent humiliating defeat. Following a ceremony at Jefferson Barracks, Gentry (appointed to the rank of Colonel by the U.S. Army for this campaign), his troops, their horses and gear boarded large barges for their long trip to Florida by way of the Mississippi River to Fort Jackson in New Orleans where they boarded boats to cross the Gulf of Mexico. Crude traveling conditions and fever took their toll on the troops and many horses were lost to rough seas. By the time they landed in Florida near where Tampa is located today, the Missouri Volunteers' numbers were reduced by nearly half, as many without horses were dismissed.

For months, the army had made numerous attempts to secure a military "victory" in battle but the Seminoles remained elusive. The army utilized the traditional military strategy where troops marched and fought in formation while the Seminoles preferred to practice a guerilla type of warfare where they would suddenly attack and disappear as quickly. Finally, on Christmas Day in 1837, the army's Indian scouts told them of a large band of Seminoles located at the northeast edge of Lake Okeechobee. Led by Osceola and two other warrior chiefs, the Seminoles laid in wait while a young U.S. Army officer, a Major Taylor, ordered Colonel Gentry to lead his Missouri Volunteers straight into this well fortified and planned ambush.

Colonel Gentry, sensing this strategy would produce a poor outcome, suggested the Missouri Volunteers flank the Indians and make a surprise attack instead. Major Taylor accused Gentry and his troops of cowardice and again ordered them to attack head-on which Gentry and his obedient Missouri Volunteers did. The Seminoles were well armed and had prepared a large clearing in the tall grass near the edge of the swamp. Immediately upon entering the clearing, Colonel Gentry and nearly half of his troops were immediately cut down and massacred in a cross fire while the Seminoles suffered fewer than a dozen casualties and easily escaped by rowing off into the swamp in their dougout canoes.

Major Taylor's written account of the event blamed the high death toll on the Missourians, stating that their cowardly attempt to run in retreat when fired upon was the cause of their deaths. This set off a heated controversy that resulted in a congressional inquiry into the matter. It was then as it is today. That is, the government was reluctant to accept the blame for its own mistakes. Major Taylor was officially cleared of wrong doing and his military career survived. In spite of his unpopularity in Missouri, Maj. Zachery Taylor was elected our 12th U.S. President in 1848.

Col. Richard Gentry was survived by his wife, Ann Hawkins Gentry, and eight children. After Richard's death, she succeeded her late husband as Columbia's postmaster thus becoming the second postmistress in the U.S. Today, several buildings in Columbia, Missouri bear the Gentry and Hawkins name including a public school.


Born 6 Jun 1797 - Cabin in the cane break, Madison Co., Kentucky
Died 22 Jan 1864 - Marion Co., Missouri

Colonel Joshua Gentry, from whom my daughters and I are descended, was Private Richard Gentry's seventh son and a brother of Colonel Richard Gentry. In 1816, Joshua left home to make his own way in the world. Joshua's first stop was St. Louis where he sought employment from Colonel John Sullivan who hired Joshua to manage his large farm on the outskirts of the city. Joshua worked for Col. Sullivan for seven years before taking the advice of a friend and moving to Northeast Missouri.

Joshua settled just west of Hannibal, Missouri in 1823 where he filed for 160 acres of land. Joshua worked the land in the summer and taught school in the winter. There he met Eula "Uly" Adeline Henry, the 13-year-old granddaughter of Colonel Malcolm Henry, another Revolutionary War veteran whose son William had moved west to the new Missouri frontier in 1817. Joshua and Adeline were married on April 11, 1826.

In the Gentry tradition, Joshua was both a leader and a servant in his community. Soon after Marion County's formation (carved out of Ralls in 1826), Joshua was commissioned the first County Sheriff by Governor George Miller and was later elected twice to that same position. When an Indian uprising occurred nearby in Iowa, the Marion County Militia was formed and Joshua was appointed to the rank of Colonel and charged with its leadership. In 1826, Joshua sold his land and moved slightly west to farm in Monroe County, Missouri. There, Joshua and Adeline's farm and family grew. Fifteen years later, in 1841, Joshua divided this 3,000 acre farm equally among his children and moved back to Marion County on a farm left to Joshua and Adeline by her parents. Joshua was an active Whig and served two terms as a Missouri State Senator representing both counties and one term as a State Congressman.

When industrialists in the East wished to build a railroad connecting Hannibal to St. Joseph, they sought a local leader to oversee construction and operation of its eastern half. Joshua Gentry was their man. Before State funds could be utilized, it was necessary to build a roadbed which could then be mortgaged to get money. So Joshua raised $50,000 backed by his personal notes to begin its construction. Subsequently, he was able to borrow $500,000 from the State to fund its completion. In 1859, the Hannibal St. Joseph Railroad ("HStJR") became the first railroad to span the state of Missouri and Joshua Gentry served as its president until his death. The HStJR was the only railroad in Missouri to repay its mortgage owed to the State due to the Civil War.

On April 3, 1860, the HStJR made history by carrying a special parcel of mail originating in Washington, D.C. and destined for St. Joseph where, upon its arrival, a series of riders would race it by horseback to Sacramento, California. The mail arrived at Hannibal many hours late that day and Joshua ordered that a train be made up consisting only of an engine, a tender, and a caboose. He instructed the engineer to stop only for fuel and water as needed. The run that day, at slightly more than 40 miles per hour, set a rail speed record that stood for many years. Thus in 1860, the first run of the Pony Express was initiated. The Pony Express was never a commercial success and was disbanded 19 months after its first run though it holds a firm place in U.S. history. And the Hannibal St. Joseph Railroad? It prospered and was,ironically, largely forgotten.

When the Civil War began, Joshua owned many slaves and was sympathetic to the Confederate cause though he refused to support the secessionist movement. The HStJR became strategically important to the Union in holding the West and much of the Civil War action in northern Missouri centered around it. As president of the railroad, Col. Gentry was charged by the Union with its defense. On the first of August, 1861, rebel forces of Capt. Clay Price surrounded Joshua's home, captured him and held him hostage. This act prompted General Hurlbut of the Northern forces to order the capture of leading Marion County citizens sympathetic to the Confederate cause (of which there were many - NE Missouri was often referred to as "Little Dixie"). Capt. Loomis and his men captured seven prominent secessionists, among them Hannibal's Mayor Hixon and issued the following notice:

Wheras, Col. Joshua Gentry has been taken by a party of rebels and is now in their hands - by order of the General in command, I have siesed several known sucessionists, who will be held as hostages for the speedy and safe return of the said Gentry, and any harm which he may sustain will be visited on these hostages, even to the taking of life. Should any attempt be made to rescue these men my orders are to shoot them at once. These orders will be obeyed.
J. Loomis, Captain, Commanding U.S. Reserve Corps."

Three days later, Joshua was released unharmed and returned to his home. Joshua and Adeline lived out their days on the Gentry Estate at the western edge of Hannibal. Joshua's health began to fail in 1862 and he died on January 22, 1864. At the time of his death, Joshua owned over 1,000 acres of farmland and numerous slaves. Today, 136 years later, the property where he lived is still owned and occupied by a descendant - Malcolm H. Gentry (Joshua's great grandson) and his wife Eva Dale Davis Gentry.

Since that Memorial Day in 1997, I have learned much about my ancestors. And I am learning more with the passage of time. It has kindled in me a special appreciation of our American heritage and a fondness for genealogy and history. I will always remember our outing that day at Jefferson Barracks with its rolling hills of lush green grass filled with limestone gravemarkers standing on end in neat rows like proud soldiers in their dress white uniforms awaiting inspection. In summary, our trip that day to Jefferson Barracks was for me, quite simply, a Memorial Day I will always remember.

John Graves - September 1998

John Graves is the administrator of a private Gentry family web site hosted at For access, e-mail your full name to:

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B.  Two "New" Gentrys Identified

Abstract – B
A heretofore unrecognized son of Samuel-II Gentry, named John, is proposed, as is a son of David-III Gentry (son of Nicholas-II), named Bailey.

John Gentry
The Lunenburg County, Virginia Court Book 7 has an entry for the October 1761 Court on p.142:

" Ordered that the Church Wardens of Cumberland Parish bind out Joseph GENTRY, orphan of John GENTRY to Samuel GENTRY, awarding bondage (Emphasis added)."
This writer has not previously seen any proposal that Samuel Gentry (son of Nicholas the Immigrant) had a son by the name of John, yet it seems that is the only explanation for the John mentioned here. On the surface it appears that both parents of the orphan boy Joseph had recently died, probably of sickness, leaving their son to be assigned care by the courts and by the church parish as was the custom. In this case, his care appears to have been assigned to his presumed grandfather, Samuel. [Note. Guardianship was not the appropriate action by the courts in this case, although that is what a modern court might assign. In colonial times such action was taken only when there was a question of real estate involved, that might have to be protected on behalf of the orphan boy until he reached the age of maturity. "Bondage" simply assigned responsibility for care and upbringing for the bound individual.]

How can we assume that this John was a son of Samuel. Several points argue for this:

  1. In all of the Lunenberg County records found to date that refer to Gentrys, only members of the extended families of Samuel and his brother David have been found to have lived there.
  2. For John to have a son, Joseph, he probably was at least twenty years old, which would give him a birth date of say 1740, give or take a couple years.
  3. Of Samuel's sons, his oldest son, Nicholas, is believed to have been married about 1743 which would have meant the latter's first son would not have been born until about 1744.
  4. Even if John had been Nicholas' son, logic would dictate that young Joseph would have been bound to his presumed grandfather Nicholas instead of to Samuel. (Nicholas was a prominent member of the Lunenburg County community and certainly available for assignment of bondage.)
  5. David Gentry had a son John who was similar in age to this John but he survived to a ripe old age in South Carolina. Further, there is no record of a Joseph Gentry among David's other children.

There is no further evidence of the young orphan Joseph in any of the records pertaining to Samuel's family. The assumption must be that he probably died in infancy or as a young boy, perhaps soon after the cited court order and for the same reasons as the death of his parents. The order of this proposed John in the family of Samuel is very uncertain, given the fact that we have no good estimate of how old either John or his son Joseph were at the time of John's death. The order of birth of Samuel's younger children is very questionable at best. This John adds nothing to the ease of determining such order.

Bailey Gentry
Nowhere in "The Gentry Family in America", does the compiler mention a Bailey Gentry as a son or grandson of Nicholas-II Gentry. However, in the tax lists for Trinity Parish, Louisa County, Virginia, there is a Bailey Gentry who appears for the first time in 1769 as a tithable individual, listed in the household of David Gentry. Bailey appears again with David in 1770 and 1771, but not in 1773, (records for 1772 are missing). In 1773, a Bailey Gentry is listed for St. Martin's Parish (also Louisa County), in the household of a Benjamin Cook. In 1774, Bailey Gentry is listed individually. Thereafter he is not to be found. Meanwhile, David Gentry was listed by himself in 1768, 1774 and 1775. This argues for the following set of circumstances:

  1. Bailey was a son of David-III (son of Nicholas-II), born in 1753 or before (he was liable for tax at the age of 16).
  2. Bailey left home in 1773, moving to the neighboring parish of St. Martin's where he perhaps served as an overseer for Benjamin Cook.
  3. Bailey died sometime shortly after 1774.

If a son of David, then Bailey was presumably the oldest of David's children when one considers the possible dates of birth of David's other children. By coincidence, he was apparently an older brother of the Revolutionary War Richard Gentry mentioned in the accompanying article by John Graves. It is of interest to note that David's son, David Jr. had a son named Bailey (born much too late, of course, to be this Bailey), so the name appears to possibly run in the family.

Neither one of these early Gentrys had any bearing on future Gentry generations since both died at an early age and presumably left no continuing descendants. But they are of interest in filling out a little more of the picture of these early Gentry families. Minor revisions September 2013

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