John Samuel Hollingshead was the son of Judge John Hollingshead and his wife, the former Mary Drain.  The District of Columbia was a hotbed for the growing sport of baseball after the Great War for Slavery; even as a teen he was playing for the best amateur nines in the District.  In 1872, when the Nationals joined the National Association, he was an infielder.  A year later, the Olympics joined the National Association and Holly played for that squad, too.  He was on the 1875 roster – and despite being 22 years old, he was their onfield captain.

At some point in the late 1870s, Hollingshead went back to amateur baseball and, like so many of his baseball friends, he was earning a regular salary as a government clerk.  Hollingshead left the Internal Revenue Service to manage the 1884 Nationals squad that joined the American Association but that didn’t go as well as one would like (they went 12 – 50) so he went back to being a clerk, this time for the Department of the Interior.  By most descriptions, he was a kind and friendly man.

He married the former Mary Windsor Wilson in 1879, but she died about six months after they married.  He later married Katherine Lee in 1894, who brought into the family a daughter, Lee Moore Hekimian.  Hekimian was listed as the lone survivor at the time Hollingshead passed away at his room at the John Dickson Home, a home for single (and mostly older) gentlemen; he passed on October 6, 1926. Hollingshead is buried in Glenwood Cemetery, not far from his first wife, in a family plot.

Notes:

1860, 1870, 1880, 1900, 1910, 1920 US Census
Washington DC Marriage Records

“Pioneer Capital Ball Player Dies,” Washington (DC) Evening Star, October 7, 1926: 7.