Long one of Pittsburgh's wealthiest congregations, Shadyside Presbyterian was founded in 1867 by prominent landowners Thomas Aiken and William Negley. After constructing two unsatisfactory churches on the same site, the congregation turned to the Boston-based successor firm to H. H. Richardson, whose style then dominated Pittsburgh. The predictable outcome was a restatement of Richardson's Trinity Church in Boston. Here the muscular central block and pyramidal cap clearly recall Trinity, but Shadyside Presbyterian is broader and has a lower profile. In more densely packed city streets, the church's understated grandeur would be lost, but in this verdant setting amid nineteenth-century homes, the scaled-down facade, external narthex, and transept ends produce an unusually powerful neighborhood church. Another contextual touch is the inclusion of many windows, far more numerous here than in the Boston prototype, perhaps in response to Pittsburgh's dark and smoky skies.