In 1880, Eli and Lucy had three children. Two boys were "at school": Edward, age 13 (born about 1867 in Kansas}; and William, age 7 (born in Indian ). The boys could read and write. The youngest child was daughter Alyna or Alyssa, age 4, (born in Indian Territory). Those listed living on the same block as the Gentry family included black, mulatto, and white people. Some of the blacks and whites were listed as servants, but not all.

These facts form the basis for research on this family.

In 1878 and 1879, the Denison Daily News must have made Eli Gentry something of a local celebrity with its frequent reports of his problems with the criminal justice system. On August 29, 1878, editor B. C. Murray recounted: "Wade Hudson, a colored individual, who had a difficulty on the 21st day of August, with one Featherstone, also colored, in Eli Gentry's billiard room on Austin Avenue, in which he cut Featherstone several times with a pocket-knife, had his examination in Judge Kirk's court Wednesday morning. Hudson was ordered to give bonds in the sum of $500 for his appearance at the next term of the district court; as he is unable to do so, he will be taken to the Sherman jail."

On October 12, the News asserted, "Eli Gentry, the proprietor of a saloon on Austin Avenue, frequented by colored persons, was arrested on Tuesday night by Constable Spence and turned over to Deputy United States Marshal Williams, on the charge of having introduced spirituous liquors into the Indian Territory. He was taken to Fort Smith on the 12 o'clock (midnight) train. As the punishment for introducing liquors into the Territory was from six months to two years in the penitentiary, it seems probable that Eli has got himself into a very bad scrape." Even so, on October 26 the News reported, "Eli Gentry, who was arrested and taken to Fort Smith, Arkansas, for introducing spirituous liquors into the Indian Territory, will, we understand, be released."

Things were quiet for a few months, but on February 11, 1879, the News carried this report: "Eli Gentry, the proprietor of the bar-room on Austin Avenue, was tried Monday in Justice Riddle's court on the charge of allowing gaming on his premises. The jury brought in a verdict of guilty and assessed the fine at ten dollars and costs. The defendant was represented by A. B. Person, Esq., and the State by the county attorney, Capt. Turner."

The next day, editor Murray returned, reporting: "Eli Gentry, the proprietor of the saloon on Austin Avenue, who was fined in Justice Riddle's court for permitting gaming on his premises, was again hauled over the coals Tuesday on two indictments found against him by the Grand Jury, for violation of the Sunday law. One of the cases was dismissed, but in the other he was fined $25 and costs by a jury."

For several months Eli escaped notice, but on August 21, the News had this to say: "Mayor's Court. The time of this court was mostly occupied Wednesday morning with the trial of parties charged with vagrancy. Two of them were acquitted ... and the trial of Walter Collelt and W. H. Danforth, alias Sport, was postponed until this morning. Two colored men, Eli Gentry and Mark Chiles, were fined the usual amount. They proved to be cash customers, quite a rarity lately."

Eli was not always on the wrong side of the law. On November 7, 1879, the News printed this "Card of Thanks" addressed to Messrs. Waterman, Star & Co.: "Gentlemen—Please accept our thanks for the kind donation of a fine hat to our festival Wednesday evening. Yours respectfully, Eli Gentry, Geo. F. Franklin, Wm. T. Morgan, Ben White, and H. Gilliean. Committee on arrangements, Gate City Lodge. The hat was voted to Henry Gilliean over four competitors. Miss Joe Clark was voted the fine gold ring."

In the fall of 1879, Eli Gentry was organizing a "colored minstrel troupe" to tour in Indian Territory and Texas.  Murray, editor of the Denison Daily News, took a great interest in this development, following it with numerous small reports. "One of the troupe was connected with the Georgia minstrels, and all have some experience in the business." Two days later: "Gentry has in his troupe two members of the famous Georgia minstrels."

Murray was referring to "Brooker and Clayton's Georgia Minstrels," the first successful African American black face minstrel troupe. According to Wikipedia: "The company was formed in 1865.  Under the management of Charles Hicks, the company enjoyed success on tour through the northeastern United States in 1865 and 1866.  They billed themselves as "The Only Simon Pure Negro Troupe in the World," and their act as an "authentic" portrayal of black plantation life...Large crowds watched them perform in many cities.  They repeatedly outperformed both black and white rival throughout 1866....Perhaps most significantly, the success of the Georgia Minstrels spawned many imitators.  Other black troups found great success and acceptance, and black minstrelsy took off as a genre in its own right."

On September 28, the News printed this puckish account: "Aunt Jane and Lou Rodgers, two colored women, whose combined weight is about 700 pounds, were hunting for some officers of the law Saturday evening at a late hour, for the purpose of having Eli Gentry arrested. They charged that Eli had kidnapped their fair daughters, such blushing damsels just budding into sweet sixteen, for the purpose of entering them as recruits in his troupe of colored minstrels, and that the parties would leave for Muskogee that night. Mary Allen, Aunt Jane's fair daughter, has a real good voice, as those who have been awakened by it from their morning naps can testify. We did not learn how the matter was arranged."

Apparently this contretemps did not interfere with scheduled appearances. On October 7, Murray reported from the "Sixth Annual Fair of the Indian Territory" at Muskogee: "Eli Gentry's minstrel troupe, from Denison, have drawn crowded houses day and night." The reception at home was less enthusiastic, as Murray wrote on October 26: "Eli Gentry's colored minstrel troupe that gave an entertainment at the old Kansas City store Friday night, did not have a very large audience. Gentry's receipts at the door was about ten dollars, his expenses thirty."

Editor Murray dropped his tongue-in-cheek tone, if not his racial preoccupation, on January 29, 1880, when he reported a somber tragedy: "Eli Gentry's little child died Tuesday and was buried Wednesday. It was the largest colored funeral ever witnessed in the city." This must have been before the 1880 Census was taken.

As we have seen, as early as 1878, Eli operated a saloon on South Austin Avenue. The 1887 City Directory listed Eli running a "club room" and rooming with Jennie Duncan at 207 West Owings. Lucy was a laundress living with the children at 205 West Woodard Street. Son William, now 14, worked at a steam laundry. His older brother Edward Gentry had become a barber at Thompson & Lott, operated by two African Americans, Joseph Thompson and Sylvester Lott. This business, billed as “barbers, shop and bath rooms,” occupied space at 104 West Main Street (the Lebrecht Building, built in 1884), at the busy southwest corner of Main Street and Houston Avenue.

Four years later, in 1891, Eli's "club rooms" were "over" 209 South Austin Avenue. And he was back home with Lucy at 205 West Woodard Street.  Edward was now a barber with Eugene Lafon at 111 East Main Street. He was rooming with another "colored" barber, Jesse A. Coleman. Jesse's barber shop was at 209 South Austin Avenue, along with Eli's club; and he lived at 104 West Bond Street.

Also in 1891, Edward married Susie, a black woman born in October 1862 in Tennessee. In October 1892, they would have a daughter, Bernice.

After 1891, there is no record of Eli Gentry or his wife Lucy or daughter Alyna/Alyssa in Denison.

The 1913 Denison City Directory listed someone named William Gentry, a laborer on the MK&T Railway. He boarded at "Construction Car." This person was not identified as colored.  In 1915, William Gentry (colored) was a laborer. His wife was Ella, and he lived at 304 East Owing Street. In 1921, William Gentry (colored) was listed as a laborer boarding at 406 East Nelson Street.

In 1915, a man named Edward Gentry (colored) was listed in the Denison City Directory. He had a wife named Lucy and was a laborer; he lived at the rear of 526 West Morgan Street. He could not be Edward D. Gentry the barber, because he died in 1908.

In 1917, the Denison City Directory listed Mrs. Lucy Gentry (colored) living at 126 East Washington Street. In 1921 she was a laundress living at 127 East Johnson Street. It is unclear whether this Lucy Gentry was Eli's wife, returning to Denison after many years away (she would have been 75 years old in 1917), or the wife of Edward Gentry mentioned in 1915.

The Denison Press of December 7, 1938, listed this real estate transaction: "L. E. Kinnard to Eli Gentry, lots 1, 2, 3, 4 and 5, West Fulton addition to Van Alstyne, $175, Nov. 28, 1938." A man named Eli Gentry is buried in Van Alstyne TX Cemetery. His birth date was May 26, 1885, but the death date on his gravestone is illegible. His wife was Chloe. This information is from Find a Grave. 

This Eli Gentry almost surely is not our Denison Eli Gentry.

Another Eli Gentry is buried in the Old Agency Cemetery in Muskogee, Oklahoma. Find-a-Grave reports his death as May 12, 1897, at age 53, and his birth date unknown. If he was 53 at death, he would have been born around 1844.

The Old Agency Cemetery was created "soon after the Muskogee Creek agency was established at Fern Mountain in 1857." One website says it "deserves to be put on the National Register of Historic Places because it is a testament to an African–Native American community unlike any other in the country."

The "Creek Freedmen" were former African slaves of the Creek Nation of Indians, one of the Five Civilized Tribes. They were emancipated after the Civil War.  By a new treaty signed in 1866 between the United States and the Creek Nation, they were adopted as tribal citizens with full rights of Indians.

In 1891 the Creek Council made a complete census of citizens in the Creek Nation, listing the 48 political towns and their respective population totals. This enumeration included 9,639 Creek Indians and 4,203 Negroes for a total figure of 13,842. Whites, Chinese and Indians from other tribes were not listed, since they were not citizens of the Creek Nation in 1891.

In 1979, the Muscogee (Creek) Nation "de-citizenized" the Creek Freedmen descendants by reorganizing the Creek tribal government. The constitutional organizers found a way to disenfranchise its black slave descendants by a vote of a select group of people, which the Freedmen descendants believed was illegal. Legal and other battles continue to this day.

Currently the Old Agency Cemetery is severely vandalized and overgrown. Of an estimated 1,000 graves, only a quarter are marked or otherwise identified. The Oklahoma Cemetery Preservation Association has plans to restore this abandoned and neglected historical place.

It seems quite likely that our Eli Gentry was of African Creek heritage. He was born in Indian Territory and is documented having relationships with people in Muskogee, with his minstrel group performing at the 1879 Indian Fair there and his activities providing liquor to people in Indian Territory. It certainly is possible that he was the Eli Gentry buried at Old Agency Cemetery; however, it is not certain.

One other Gentry is buried at the Old Agency Cemetery in Muskogee—Willie Gentry, birth unknown and death December 1904. His father was Captain William Elijah Gentry (born March 11, 1842, in Calhoun County, Mississippi; died October 25, 1908, in Council Hill, McIntosh, Oklahoma). Willie's mother was Lucy Perryman (born 1847 in Gatesville, Wagoner, Indian Territory). There is a profile of Captain W. E. Gentry in Harry F. O'Beirne, Leaders and Leading Men of the Indian Territory, with Interesting Biographical Sketches, vol. 1: Choctaws and Chickasaws (Chicago: American Publishers Association, 1891).

We see two similar configurations: (1) Our Eli Gentry with wife Lucy and son William. (2) W. E. (Eli-jah) Gentry with wife Lucy (the first of four wives) and son Willie. Careful examination indicates that these cannot be the same people.