How come? Because, as many of us can attest, it's never a bad idea to try getting in good with the in-laws.
Most of what we now call the South Side was owned by John Ormsby, a British soldier who'd fought in the French and Indian War. Ormsby had been stationed in the area for years, though he never seemed anxious to put his own stamp on it. As his commanding officer wrote in 1763, originally "neither Ormsby, nor any other Inhabitant had ever any right of Property to any House or Ground at this place but merely the use of them, while they remained here, and no longer." And they were "always obliged when they went away, to deliver the keys of their Houses to the Commanding Officer, who gave them to other People."
Sounds downright socialistic, so of course that couldn't last. As time went on, English soldiers began spreading the empire in another way: by accepting large land grants on the frontier in exchange for service. In 1770, Ormsby got a grant of 3,000 acres of land. He used it mostly for farming, a task for which the fairly level flood plain must have been well suited.
But of course, that couldn't last either. One of Ormsby's daughters, Jane, married a young doctor, Nathaniel Bedford, who had a larger vision for the area.
Bedford's skill as a physician is a bit difficult to discern, though his wife died shortly after his marriage. In any case, Bedford found himself a widower, but with a large amount of real estate left to him by his wife. (If I were Henny Youngman, I'd joke that this was the best of both worlds. But like I say -- it never hurts to start getting in good with the in-laws, even if you're not actually married yet.) Suddenly Bedford found himself possessed of land that stretched from roughly South 6th to South 17th streets.
Bedford soon proved to have other skills than medicine -- which perhaps is a good thing, all things considered. Within the boundaries of his estate, he laid out the plan for a town he called "Birmingham," after the English city where he was born. The streets running from north to south were given numbers, while the central thoroughfare, Carson Street, was named after a ship captain friend of his. The rest of the streets, however, were named after Bedford's late wife and her sisters, the daughters of John Ormsby himself: Sidney, Sarah, Mary, and Josephine. (Bedford also named Bedford Square after the person who would have to be the widower's best friend from here on out -- himself.)
The street pattern was extended as the South Side continued to develop; indeed, by the mid-19th century, most of the women Bedford's streets were named after were living next door to each other in a row of mansions arranged between South 21st and South 24th streets.
As Leland Baldwin wrote in Pittsburgh: The story of a city, "[E]ach [had] her own house and beautiful well-kept gardens extending down to the river." Sidney Street was named after Sidney Page, whose home was called "The Dingle" (and whose husband, one suspects, was never taken seriously ever again). Sarah street was named for Sarah Phillips, who lived in "The Orchard," while Mary Street was named for Mary Phillips, who dwelled in the "White House" back when that was something to be proud of.
Baldwin also mentions a Josephine Yard and an Oliveretta Wharton, whose husband's name can still be found in the South Side today. Her unusual first name, apparently, didn't fit on Bedford's street maps; it's perhaps best explained by the fact that her brother, the family's lone son, was named Oliver.
Oliver Ormsby's own estate, incidentally, became known as Mount Oliver, which is what we still call the tiny municipality located not far from the South Side. Oliver, it seems, didn't feel a need to name his property after anyone.
But then you probably don't have to worry about impressing the in-laws if you came by the estate on your own. Which is too bad for the rest of us.