When the spanking new Toronto Jail, that grand “palace for prisoners,” opened its doors on the east side of the Don River in 1864, George Littleton Allen, the man who had governed its bleak predecessor, moved into a suite of apartments in the jail’s central administrative block.
Heading up the administration of the Don Jail was a demanding and often thankless job. In its 110-plus years of operation, the jail was almost always overcrowded, with a population ranging from inmates doing a few days’ time for public drunkenness to dangerous criminals awaiting trial or appeal for assault or murder. The governor, always a man, would have to answer to his superiors, the public, and the press for anything that went wrong under his watch, which included bad food, jail breaks, riots, allegations of brutality against jail staff, or the suicide of an inmate. Worse still, with the ultimate penalty for murder at the time being death by hanging, forty-four men were executed at the jail between 1872 and 1962. The governor would act as uncomfortable host on these grim occasions. As for remuneration, it was calculated in 1965 that the salary of the incoming governor, Gerald Percy Whitehead, would be less than that of a junior high school vice-principal.
And yet there were always takers for the position. Governor Allen was not one of the worthier ones: he was known to sell “strong drink” to inmates to supplement his income. His successor, John Green, was a much more commendable leader. In 1888, with overcrowding in the jail now chronic, Green had the good fortune of moving into a beautiful, purpose-built house just to the southeast of his workplace, where he lived until his death in 1900.
After a succession of improper or incompetent governors in the early part of the twentieth century, the City of Toronto and the province of Ontario opted to favour returned soldiers for the post. The first of these military types was Major George Hedley Basher, who ruled the Don with an iron fist between 1919 and 1931. A much more progressive, if short-lived, soldier-turned-governor was Charles Sanderson. In 1951, he had the walls of the jail painted in pretty pastel shades. Inmates were allowed to play card games and quoits.
The second half of the twentieth century ushered in sweeping changes. Amid ongoing criticism of deplorable conditions in the Old Don Jail, a new wing was built against its east side. This facility opened in 1958. Terminology also changed. By the time the Old Don was cleared of all its inmates at the end of 1977, the administrative head of the jail was no longer a governor but a superintendent. Some gubernatorial traces remain, though: a fragment of wallpaper at ceiling level in the historic building, now restored, marks the location of the governor’s erstwhile apartments. The east wing of the jail has been torn down, but the Governor’s House still stands adjacent to the Old Don Jail; it has taken on a new and more benevolent life, however, as a non-profit hospice for children.