The original building was completed in 1864 and was reopened in 2013 to serve as the administrative wing of Bridgepoint Active Healthcare, a rehabilitation hospital located adjacent to the jail.

Designed by architect William Thomas in 1852,[2] it was constructed with a distinctive facade in the Italianate style, with a pedimented central pavilion and vermiculated columns flanking the main entrance portico.

[7] These conditions were also brought to light by a controversial article[8] appearing in the Toronto Star after journalist Linda Diebel was smuggled into the prison by Dave Levac, a sympathetic Ontario MPP.

Mr. Levac faced censure by the Integrity Commissioner for bringing in the reporter, whom he led Jail officials to believe was a member of his staff, as part of his entourage.

Starting with the execution of John Boyd in January 1908, hangings at the jail took place in an indoor chamber, which was a converted washroom, at the northeast corner of the old building.

The indoor facility was seen as an improvement because outdoor executions were quasi-public (at the hanging of Fred Lee Rice on July 18, 1902, crowds had lined surrounding rooftops to see something of the spectacle) and because the condemned didn't have to walk as far.

[citation needed] The best-known Canadian hangmen, such as John Radclive, Arthur Ellis and Camille Blanchard, hanged men at the Toronto Jail.

About 20 per cent of the former jail's heritage interior was preserved, including the centre block's half-octagonal rotunda featuring clerestory windows, as well as original iron railings and balconies supported by griffin and serpent cast-iron brackets.

[6] In 2008, the City of Toronto's heritage preservation staff and some Councillors wanted Bridgepoint Health to retain the steel bars on all of the old jail's windows.

[16] The east wing was formally decommissioned on January 6, 2014, at which point it too was transferred to Bridgepoint Health and demolished in March and April of that same year.

[19] The prison and hospital also served as the location of the fictional Dyad institute in the Canadian TV show Orphan Black.