The area never achieved the fashionable cachet anticipated by the scale of the architecture and St Paul's church, being soon eclipsed by
Clifton. Rather than the fine domestic residences planned by the developers, by the end of the 19th century there were many small business based around the square, particularly involving boot & shoe manufacture, and ancillary services for printing such as ink making and cardboard box making. By 1916
The Salvation Army opened two hostels for men and women in the area. Bristol suffered from
heavy bombing in World War II and Portland Square did not escape. A raid on 2 December 1940 killed 40 people and destroyed Dean Street, to the North of the Square. and by 1951 the
Ordnance Survey map described parts of the Square as "in ruins". Despite this, little progress was made and the North West corner of the Square still required timber
shoring to support buildings damaged by wartime bomb damage. A gradual decline of St Paul's in general reached its nadir around the
rioting of 1980. Both Portland and Brunswick squares developed a reputation for
prostitution and drug-dealing. ==Redevelopment==