An interesting account in W.J.L. Sullivan’s book 12 Years in the Saddle casts light on what became of Orlando N. Hollingsworth in the final years of his life, and explains why specific information may be hard to find. Sullivan was a Texas Ranger, and his book chronicles incidents in his years of service in the final part of the 19th century. Here’s the story Sullivan has to tell:
In 1891, he had a warrant to arrest O.N. Hollingsworth, who lived 18 miles west of Quanah and 7 miles south of Kirkland. He rode out to Hollingsworth’s place with two other lawmen whom Hollingsworth knew, so they sent Sullivan first to the house, since he was unknown to Hollingsworth and this would avoid spooking him. Sullivan arrived at Hollingsworth’s house told a young man — perhaps Hollingsworth’s son — came out. Sullivan told the young man that he and his horse were badly jaded and he’d like to spend the night.
He was invited inside and eventually told Hollingsworth that he had papers for him. Hollingsworth’s wife had sat reading all the while, and at that point offered Sullivan food. He suspected she wanted him to go to their outside eating area to eat the meal she offered him, so her husband could high-tail it. He made a point of not letting Hollingsworth out of his sight, and when Hollingsworth walked to a bureau that had two guns on it, he asked Hollingsworth to step back — at which point Hollingsworth broke into tears.
The other two lawmen then arrived and Mrs. Hollingsworth made beds for the three lawmen and they spent the night, taking Hollingsworth away the next morning. Evidently, he had stolen or embezzled money from the state due to the “high-living” habits of his children, which had ruined him financially.
He was given bail, and disappeared — forever, according to Sullivan. His wife then sold their house and two daughters sold a section each of land that they owned to pay the bail.
Sullivan says that the old gentleman O.N. Hollingsworth whom he arrested was highly educated, had an office in Austin, had been a teacher, and was about 65 years old in 1891. Though that age would make the O.N. Hollingsworth of Sullivan’s record ten years older than Orlando Newton Hollingsworth was, I’m quite sure the O.N. Hollingsworth about whom Sullivan is reporting was Orlando Newton Hollingsworth. This account explains why it appears he just vanished at the end of his life and there is not a clear date and place of death for him. He had skipped bail after being arrested in Texas, as census data show us, he hied himself away to Atlanta and lived the final years of his life there, dying under a cloud so that there are no obituaries — that I can find — in either Atlanta or Texas.
Here’s a series of newspaper articles from the Austin-American Statesman in 1891 that explain in detail what had precipitated Orlando’s arrest:
The 1880 federal census shows Orlando and his family living in Austin, Texas, where Orlando’s occupation was Secretary of the Texas Board of Education. By 1900, after Orlando had been arrested in 1891 and had skipped out on his bail and Sullivan reported that he had “never heard of Hollingsworth since,” Orlando and his family had gone to the Edgewood section of Atlanta, where the family is found on the 1900 federal census, with Orlando having no occupation listed.
The Dallas city directory for 1893 suggests that in that year, Orlando and wife Ruth (née Ruth Grace Katherine Platner) were living separate from each othe — one suspects because Orlando was on the lam. The city directory lists Ruth G.K. Hollingsworth (Mrs. O.N) on the fourth floor of the Middleton Building, over 395 Main, with her sons Orlando Jr. and Seth living with her, but no mention of her husband Orlando Sr.
Orlando is found on the 1910 federal census living in Decatur, Georgia, with his occupation given as real estate agent. His household in 1910 consists of himself, wife Kate, and daughter Jean.
By 1920, Ruth G. Hollingsworth appears on the federal census in Glendale, Los Angeles County, California, with daughters Jean and Joicy living with her. Ruth is listed as a widow. Census data appear to indicate, then, that Orlando Newton Hollingworth died between 1910 and 1920, probably in Decatur, Georgia.
 W.J.L. Sullivan, 12 Years in the Saddle: For Law and Order on the Frontiers of Texas (Chicago: e-artnow, 2018) (unpaginated).
 1880 federal census, Travis County, Texas, Austin, p. 222B, ED 134 (dwelling/family 57; 3 June).
 1900 federal census, Fulton County, Georgia, Atlanta-Edgewood, p. 16, ED 39 (13 June).
 Morrison and Fourmy’s General Directory of the City of Dallas, 1893-4 (Galveston: Morrison & Fourmy, 1894), p. 274.
 1910 federal census, DeKalb County, Georgia, Decatur, p. 19B, ED 20 (dwelling 386/family 393; 3 May).
 1920 federal census, Los Angeles County, California, Glendale, p. 5A, ED 22 (406 East Dryden; dwelling 112/family 113).