In the Footsteps of Ambrose Small

The echoes of Toronto’s torn-down buildings are loud and empty.

If there were international prizes for destroying a city’s heritage, Hogtown’s prowess at demolishing its own history would take a gold every time.

Sometimes all that’s left is empty space – alleyways, parking lots, public squares.

I’m writing a book and companion podcast about the disappearance of Toronto theatre magnate Ambrose Small on December 2nd, 1919.

Trying to find more than a handful of buildings in which Ambrose Small and his wife, Theresa, might have set foot is surprisingly difficult.

There’s the Smalls’ house in Rosedale, the Dominion Bank building at King and Yonge, Massey Hall, the Royal Alex and the King Eddy – but that’s about it.

Dominion Bank Before - In the Footsteps of Ambrose Small
Dominion Bank Before
Dominion Bank After
Dominion Bank After – The Dominion Bank eventually merged with the Bank of Toronto to become the Toronto Dominion Bank, better known today simply as ‘TD.’ Now it’s mixed residential and hotel. But you can still walk in and look at most of the spaces.

The Dominion Bank Building, at the southwest corner of King and Yonge, plays a key part in the Ambrose Small mystery.

The ‘Before’ image here is from an old postcard.

On December 1st, 1919, in an upper boardroom, Ambrose and Theresa Small received a $1-million dollar down payment cheque for the sale of their theatre chain.

The next day, the Smalls retuned and Ambrose deposited the cheque in the central banking room with its soaring two-storey ceilings.

Then there’s the matter of the $200,000 worth of bonds that Ambrose’s secretary, John Doughty, removed from the Smalls’ safe-deposit box in the basement.

Ambrose Small disappeared on the evening of December 2nd, 1919, just a few hours after depositing the million-dollar cheque.

John Doughty had removed the bonds over the course of three visits to the bank – on December 1st and 2nd.

Main Banking Room
Main Banking Room – Now a swanky events venue the main banking room is where Ambrose deposited the million-dollar down-payment cheque.
Safe Deposit Room
Now often used to store stacking chairs, the safe-deposit room is where Ambrose Small’s secretary, John (Jack) Doughty removed $200,000 worth of bonds from Small’s safe-deposit box.

But for our purposes, the Dominion Bank building is a rarity, first, in the sense that it survived, and second, that it directly ties into the mystery.

Even when one tries to find buildings that the Smalls might have been in throughout the course of their everyday lives – never mind during Ambrose’s last days – the pickings are slim.

In some cases where once there was something, there is now nothing – not even a new building.

Carls Rite Before - In the Footsteps of Ambrose Small
Carls Rite Before
Carls Rite After
Carls Rite After – Theresa Small attended many different charity events at the Carls-Rite Hotel, which once loomed at the corner of Front and Lower Simcoe Streets, today the site of a scenic parking lot.

Theresa Small was an active and prominent fundraiser for various charities.

As such, she attended numerous charity events at the Carl-Rite Hotel, later renamed the Union Hotel.

It stood on the northeast corner of Front and Lower Simcoe streets, kitty-corner to the present-day Toronto Convention Centre.

Today, its pleasantly rambling bulk is absent in favour of – a parking lot.

The ‘Before’ image is an old postcard from its Union Hotel days.

But you can see that the building just visible at the far right has survived.

It’s home to the Canyon Creek Chop House.

Armouries Before - In the Footsteps of Ambrose Small
Armouries Before
Armouries After
Armouries After – The Toronto Armouries opened in 1894 and were torn down in 1963. They were located on the southeast block of University Avenue and – what else – Armoury Street. The ‘Before’ photo is from Toronto Archives, Fonds 124, Fl0001, Id 0064.

The Toronto Armouries resided in a wonderfully castle-like building on the present-day site of the Provincial Courts building on University Avenue.

Part of the space once occupied by the Armouries is now an open area almost purpose-made for protests.

Ambrose and Theresa Small attended the Motor Show (the pre-cursor of today’s Auto Show) at the Armouries in 1912.

During World War I Theresa Small also attended events there as a member of the Imperial Order Daughters of the Empire (IODE) a sort of Monarchist benevolent society.

GOH Before - In the Footsteps of Ambrose Small
GOH Before
GOH After
GOH After – The Grand Opera House on Adelaide Street West was Ambrose Small’s Toronto Headquarters. According to legend, but not likely fact, Ambrose Small met his end in the basement furnace room. The ‘Before’ photo is from the City of Toronto Archives, Fonds 1231, f1231_it0843.

As for Ambrose Small’s headquarters, the Grand Opera House on the south side of Adelaide Street, just west of Yonge, the only thing that survives today is an alleyway called Grand Opera Lane.

And here’s how desperate this search has become – Grand Opera Lane was an alleyway back in the day.

It ran its present course south off Adelaide on the east side of the Grand Opera House.

That’s more than you can say for Johnston’s Lane that ran down the west side of the building.

Johnston’s Lane included a private exit from the building so that Ambrose could come and go without having to worry about meeting the numerous people he’d wronged, to whom he refused to pay monies owed, or to whom he’d simply been a jerk.

Alas, as you can see from the present-day photo, Johnston’s Lane has long since been built over.

For that matter, you can’t even see any sky in today’s photo, so dense are the looming skyscrapers.

That’s all the search for Ambrose Small leaves us – a parking lot, a small public square, and … an alleyway.



Geordie Telfer has written several non-fiction books of Canadian history and trivia for various imprints of Folklore Publishing in Edmonton. You can find his Ambrose Small podcast, Hogtown Empire, at or subscribe through iTunes.