
The little human-sized buildings along Fort Pitt Boulevard originally faced the Monongahela Wharf, where the steamboats lined up.

Built in 1927, this Fourth Avenue tower was designed by John M. Donn, a Washington architect known for government buildings who seems not to have done anything else around here. (Update: This is incorrect; Donn also designed the Cathedral Mansions apartments in Shadyside.) The curious ornamental obelisks at the corners of the cap were the inspiration for Philip Johnson’s Tomb of the Unknown Bowler down the street.
The Point was mostly a run-down warehouse district after the Second World War, which made it an ideal showcase for the modernist ideal of urban redevelopment. The part nearest the confluence of the rivers was set aside for a park (which took a quarter-century to realize), and the rest was demolished to make way for gleaming modern towers. It was a great success, and it probably did untold damage here and in other cities. Its success convinced a generation of urban planners that the key to prosperous development was to replace crowded urban districts with sterile modern towers. It almost never worked; Gateway Center was a lucky anomaly, and old Pa Pitt would suggest that the park and landscaping had more to do with its success than the architecture of the buildings—although he does think the three original Gateway Center towers (the silver cruciform towers in the middle right of this picture) are masterpieces of their kind. That, too, was a lucky accident: they were meant to be sheathed in brick, which would have made them pedestrian stacks of offices, but postwar shortages made it more economical to give them the gleaming metal surfaces you see here.
This hotel was built in 1959 as the Pittsburgh Hilton & Towers. It was probably meant by its architect to have the elegance of simplicity, and no one will argue about the simplicity. In the 2000s it was decided to add an egregiously mismatched postmodern front to the building; the Hilton, though, seemed to be constantly running out of money, and the addition sat half-finished for years. It was finally completed under the new owners.