When that photo was made, Oklahoma was still "O.T." (Oklahoma Territory). It wouldn't become a state - the 46th - until 16 November 1907.
According to a reporter who was present, Guthrie sprang from the prairie in the afternoon of the first Land Rush Day, 22 April 1889. People had been lining up for weeks along the Kansas-O.T. border, waiting for the signal that Oklahoma Territory was open for settlement by non-Indians.
The signal was given at noon sharp and thousands rushed to stake claims to free land. By sundown, an estimated 10,000 souls were residents of brand-new Guthrie, where 24 hours earlier there had been nothing but open prairie and tumbleweeds. Lack of water and food forced about two-thirds to return to "civilization" in the first week.
Dovie and Robyn's father, Thomas P. CUPP, is listed in the 1892 Guthrie City Directory as a "Homesteader of Logan County", but didn't necessarily participate in the Land Rush. Their mother, the former Sarah E. "Emma" HUMMER had been a teacher in Lyon County, Kansas.
When Emma and Tom married in Lyon Co. on 28 June 1888, Tom was a resident of Henrietta, Clay Co, Texas, indicating they met while he was visiting his parents south of Emporia. After the wedding, he took Emma back to Henrietta. Robyn was born there the following May. Second and last child, Dovie, was probably born in Texas too, in 1891.
The family's bliss was short-lived. Tom died in 1898. Emma's father, Wm Martin HUMMER, died the following year and was buried next to Tom in the family plot at Guthrie's Summit View Cemetery.
After the death of her husband and then her father, Emma wrote to Mary (McClellan) CUPP, her mother-in-law in Kansas, that she wished she had gone to college, because teaching positions in Guthrie were only given to those who had. (At that time, a formal education wasn't required to teach school in Kansas.) Lacking means to support herself and two young children, she remarried in 1901, to James ARCHER, who had come to O.T. from the same area of Kansas as Emma and Tom.
By June of 1905, Emma had begun divorce proceedings against Archer. On 9th June, she and Dovie were in downtown Guthrie in a horse-drawn buggy. A passing street car spooked the horse, and both were thrown under the wheels of the street car. Emma died instantly. Dovie followed her a few hours later, after her mangled legs had been amputated in a futile attempt to save her life.
By sundown, mother and daughter had been buried in a single grave next to Tom Cupp and William Hummer. No funeral, no relatives notified until after the fact, the grave left unmarked.
Emma's sister Vera "Ollie" (Hummer) Calhoun arrived a week later to fetch the orphaned Robyn. She also filed suit on Robyn's behalf against the street car company, which settled several years later.
[From The Ravia Herald, 4 April 1908, Ravia, Johnston County, Oklahoma:
A jury in the district court at Guthrie has given a verdict for $4,000 against the Guthrie Street Car Company and in favor of the heirs of Mrs. Mary Archer, who with her daughter, Miss Dovie Cupp, was killed by a street car in that city in June, 1905. Their horse ran away, throwing them under the car wheels. The street car company has filed notice of appeal.]
Ironically, since Emma and James Archer were still legally married at the time of her death, he was entitled to part of the settlement. I have no clue what happened to the money, only that Archer didn't spend a dime on a tombstone for Emma and Dovie.
At age 20, Robyn was enumerated twice in the 1910 census. First as a servant ("cook and housework") in the home of a stone mason in Jefferson Co OK, and a month later as a "boarder" in a different household. I'm guessing he received his part of the settlement between visits from the enumerator.
On 31 Dec 1917, Robyn married the former Leila Fern LOCKWOOD of Edgerton, Rock Co, Wisconsin. By June of 1918, he was in Springfield City, Ohio, possibly where he trained to become a steamfitter. His WW1 Draft Registration card of that date and place states his dependents were a wife and mother-in-law.
Leila then divorced him, but by 24 January 1920, they were again living together in Tulsa OK. In September 1920, they remarried in Jackson Co, Missouri. As the photo below shows, they stayed together at least 19 more years before she divorced him again!
Leila returned to Wisconsin, where she died in 1965. Robyn went the other direction, to Lubbock TX, where he remarried to a woman named Ruby, and died there in 1966.