The origin of the exclamation “Holy Toledo!” is the subject of much speculation. One suggestion is the name came about because of the heavy concentration of churches located on Collingwood Boulevard, according to the Greater Toledo Convention and Visitors Bureau.
Also, the City of Toledo, Spain, after which the American city is named, is often called “the Holy City of Toledo.”
Other suggestions of origin are not religious, but may be more likely. Holy Week has always been the worst week at the box office for show business; old-time Vaudeville actors contended that any week in Toledo was Holy Week. Toledoans Joe E. Brown and Danny Thomas popularized the term as they became nationally known performers.
Another colorful possibility comes from a former policeman who joined the city police force in 1931. At that time, there was an alleged agreement between the police and underworld safecrackers (also known as box blowers and nitromen). Safecrackers would not be harassed if they would refrain from their activities in Toledo. Consequently, they could complete a job in Detroit, Cleveland or elsewhere and then retreat to Toledo - the “Holy Land.”
A retired policeman said he first heard the expression as a small boy around 1911 when Billy Sunday preached at an Armory on Spielbush Avenue.
Others say that “Holy Toledo” was a sarcastic expression resulting from the high proportion of bars to churches. In the pre-World War I period, it was a standing joke that you could walk out of a church on one corner and enter a bar at the next.
Regardless of the origin of the phrase, Toledo - with its many churches - has a rich religious heritage, and many of the churches have been instrumental in preserving ethnic communities.