I first learned about Ambrose Small when I was exploring the Path, the labyrinth of shops and food courts underneath the downtown core. I was on assignment for the Star and I wondered if there were any mysteries connected to the place. I was told the story of Ambrose Small and the Grand Opera House, the long-demolished theatre on Adelaide St. that was once the toast of Toronto’s entertainment scene.

The story hooked me right away — an unsolved mystery of wealth and power with plenty of schemers and scoundrels, and a city on the verge of becoming modern, struggling with change.

The only vestige of the theatre is Grand Opera Lane, a stub of a street next to Scotia Plaza. Every day, people walk by, probably unaware they are passing the scene of one of Toronto’s most enduring mysteries. In December 1919, Ambrose Small sold his theatrical empire for $1.75 million. Then he disappeared. The last place he was seen alive was that theatre.

When people went missing in 1919, their loved ones wrote to the police: My husband hasn’t been himself since the war. My son ran away from home. My wife ran off years ago to be with another man and I want to marry again, but I need to divorce her first.

They attached photos if they had them and described the details ingrained in their minds. Fred had a funny walk; Hollis had a round pimply face; Viljo the Finn had the typical Nordic complexion but had a few bullets from an earlier scrap. The police printed off photo postcards and mailed the information to detachments across the province, hoping to get lucky with a sighting.

Nobody did that for Ambrose, at least not at first. Friends and family thought he was probably celebrating the biggest business deal of his life at some faraway racetrack, or maybe he was holed up in a hotel with a girl he was sweet on. But as time passed, they began to worry. The million-dollar cheque he had deposited in the Dominion Bank, was just sitting there, untouched — like all of his accounts.

Ambrose had made a few enemies over the years. When he was a boy, his father ran the hotel and saloon next to the theatre, and as a teenager, Ambrose worked behind the scenes of the Grand as an assistant treasurer. Ambrose was ambitious, and after a few decades he owned the Grand, and controlled a network of theatres across Ontario. Some said he’d backstabbed his way to the top, but he had plenty of admirers. He was a good friend if he liked you, a “very vindictive man” if he didn’t, and downright “nasty” if you went behind his back.

Back in 1902, Ambrose married Theresa Kormann, the daughter of a local brewing family. The newlyweds moved into a mansion in Rosedale, and travelled the world by steamship.

Toronto was a Protestant town, and the Smalls were both raised Catholic. Theresa was deeply religious — educated by the Sisters of St. Joseph and a keen supporter of the church. Ambrose did most of his worshipping at the racetracks, and sometimes gave his religion as Protestant when it suited him.

On their luxurious summer vacations, Ambrose would send postcards of Hong Kong gamblers, Japanese theatres, and Hawaiian surfers to the booking agents in New York, and Theresa would bring a camera, dreaming up the presentations she would give when she returned. She was one of Toronto’s best “women speakers,” and some who listened to her tales of faraway lands swore they could feel the scorching Egyptian sand underfoot, see the long shadow of the camel at sunset.

It was an enviable life, but not without its problems. By the First World War, Ambrose had a much-younger mistress named Clara Smith. They had an intense, passionate relationship and Theresa couldn’t ignore it. She told Ambrose that Clara had to leave Toronto, and eventually, she got her way when Clara married a soldier and moved to the United States. But even in 1919 Clara was still in touch with her old flame: “Write me often sweetheart, and for my sake be a real good boy,” she wrote to Ambrose, “and if you ever feel that you can’t be true to me any longer, for God’s sake tell me and don’t let me find it out from someone else because that would kill me.”

Theresa Small, the wife of Ambrose Small, seen in this undated photo from the Toronto Star's collection at the Toronto Public Library. Toronto Star

***

The armistice flash came across the telegram wires at 3 a.m. on Nov. 11, 1918. The church bells rang, the factory whistles screamed, and Toronto woke up to the ecstasy of peace in the middle of the night. By sunrise, the downtown streets were so packed that the streetcars couldn’t make it through the crowds. Tickertape caught on the power lines and snapped in the cold November wind. Bonfires blazed. Men and women kissed and sang patriotic songs. The city went “joy crazy.”

For Ambrose, the transition to peace meant that many of his “babies” and “pets” left the city. “How many have you had?” Clara asked when he complained of his post-war loneliness. “Sometimes I think that I did you the greatest favour I could have by going away, at least I saved you any more trouble at home on that score.”

She was living in Minneapolis, where life was achingly boring. Once she paid the bills for the butcher, the electricity, and the coal, there was hardly any money left — she couldn’t even afford a manicure or a shampoo. “Not like my Amby used to take care of me. I guess God didn’t mean that Amby should be for me, so what’s the use crying? I made my bed and I suppose I must lie in it, Hard as it is,” she wrote.

She mockingly called her husband “His Nibs” in her letters. Whenever he was away for a few weeks for a sales job, she invited Ambrose to visit. “I could kill myself when I think of what a fool I have been,” she wrote. “I haven’t the least particle of love for him and I still love you with all my heart and soul.”

As Ambrose was arranging the sale of his theatres, Clara had a “beautiful nervous breakdown” and took off for a hotel in Bronxville, N.Y. She felt the lure of Broadway and the lights — her old life with Ambrose. “I just love a good time, and I wish you would come down and I will take you to all my favourite rendezvous, and have a wonderful time,” she wrote.

As world leaders hammered out the details of Germany’s surrender in the summer of 1919, the A.J. Small theatrical empire was the subject of intense negotiation. Trans-Canada Theatres Ltd., backed by Montreal railway money, was on a shopping spree, buying and leasing theatrical properties across the country in their bid for national dominance in a coast-to-coast empire.

By the First World War, Ambrose Small had a much-younger mistress named Clara Smith. Smith married a soldier and moved to the States but stated in touch with "my Amby." Toronto Star archives

They needed Ontario to complete the plan, and Ambrose had agreed to sell his holdings — the bricks-and-mortar theatres in Toronto, Hamilton, London, Peterborough, St. Thomas and Kingston, in addition to his leases and booking arrangements throughout the province. Clara worried about the “low rubbish” women in Montreal, where Ambrose had to spend a few weekends arranging the deal that fall. She was also nervous about his post-theatre freedom.

“I know you must have someone but please, please, don’t forget little honey! Someday perhaps, if you want me, we can be together all the time,” she wrote. “Let’s pray for that time to come, when we can have each other legitimately.”

She told Ambrose they should run away to the “end of the world,” but at the very least, he should come to Minneapolis in December. “His Nibs” was going to be away on a sales trip. “I wish I could be with you,” she wrote. “Would it not be great if I could just come down and cook you dinner like I did not long ago.”

***

William Shaughnessy, of Trans-Canada Theatres Ltd., trundled into the city on a train from Montreal with a $1 million cheque in his briefcase. He was a lawyer by trade, and his father, Baron Thomas Shaughnessy, was the former CPR president. On Dec. 1, 1919, William was here to finally close the deal in person.

Outside the train window, Toronto was a mess. A storm had torn through the city a couple of days ago. The mariners who were accustomed to the rhythms of the Great Lakes called these late autumn storms that blasted their ships with cold rain the “witches of November.” On land, the storm had torn crucifixes from church steeples and blown apart the flimsy tarpaper shacks that returned soldiers had built in the midst of a housing shortage.

Shaughnessy walked by the taxis and horses idling in front of Union Station. A new train station had been built down the road, but the war (and the typical bickering over who was going to pay) had delayed its opening. The new station was surrounded by construction hoarding enticing him to drink a refreshing Coca-Cola and chew Stag Tobacco, which was “Ever-lasting-ly Good.”

Further ahead on Front St., cars idled in front of the Queen’s Hotel. The charming hotel was a throwback to a simpler time, and was the place where all the prime ministers and presidents stayed when they came to town. But its days were numbered; a bigger hotel was planned to match the new train station.

Shaughnessy likely walked up Bay St. — a gauntlet of wealth — surrounded by banks, insurance companies and law firms. A lattice of streetcar wires sparked overhead, but the people in winter tweed hardly noticed. A police officer was hollering as he directed the cars, horses and streetcars. Shaughnessy was meeting Small at the law office of Osler, Hoskin & Harcourt, in the upper reaches of the Dominion Bank building. The building was one of three skyscrapers at the corner of King and Yonge, home to the corporate offices of many of the city’s new breed of money tycoons.

The Osler law firm had taken care of the real estate portion of the deal for Trans-Canada, and Shaughnessy stepped into the wooden elevator with the morning crowd, everybody’s winter wetness soaking into the carpet. Ambrose arrived at the library of their eighth-floor offices at 10 a.m., but Theresa wasn’t with him.

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The lawyers, familiar with Ontario’s Dower Act, knew that was a problem. The act was meant to protect women from neglectful husbands by automatically carving out one-third of a man’s real estate for his wife after his death, regardless of the specifications in his will. There were loopholes if you wanted to leave your wife penniless, since it was only real estate that was covered and not cash, stocks or bonds. But the Dower Act protected women like Theresa when their husbands tried to sell the family real estate. The wife had to give her blessing, and before the sale could go ahead, Theresa had to sign away her dower rights in the properties.

In this moment, Theresa held all the power, and that wasn’t ideal for Ambrose — since his wife had just come across an incriminating love letter from his mistress when he was in Montreal. The letter was strangely intimate. Clara complained about rotting teeth that had been removed in a gruesome bit of modern dentistry.

“I believe that a good percentage of sickness today is due to bad teeth, so if I were you I would get your teeth fixed up, if there is any dead ones have them out as they are sure to be infected sooner or later,” she wrote to Ambrose. “I guess you are too busy to even think of your poor little old sweetheart away out here. I do get very homesick and blue when I think of you away in Toronto. I want to see you so badly I could just run away.”

Ambrose told the lawyers that his wife was suffering from a spell of “nervous prostration,” and he and his lawyer Edward Flock left the office hoping to cajole Theresa downtown. That afternoon, the Smalls were back. At first, Theresa refused to sign the paperwork, but after she and Ambrose left the room for a short conference in private, she relented.

Whatever terms they had agreed to, whatever assurance Ambrose had given his wife, it had done the trick. She signed away her dower rights. Shaughnessy pulled the $1 million cheque from his briefcase and gave it to Ambrose. Best to give this to your wife for safekeeping, he joked, and the men all gave knowing chuckles as Ambrose handed it over to his better half.

Shaughnessy asked Theresa about her charity work and everybody left the office in a better mood, waiting for the next chapter of their lives to unfold. For the Trans-Canada men it was going to be a nationalist theatrical adventure. The Smalls had always been rich. Now they were millionaires.

***

On Dec. 2, 1919, Ambrose Small woke up in his second-floor bedroom and had a look into the backyard. A light snow was falling. He’d planned to drive his Cadillac to the theatre, but he hadn’t put the winter chains on the tires. He usually took the Church streetcar line that rolled through Rosedale, but he was running late, and so he hustled off in the direction of Bloor St. with his umbrella, hoping to catch the faster Yonge streetcar.

The Grand Opera House, a theatre on Adelaide St. that was once at the centre of Toronto's entertainment scene. Alexandra Studio

Small hopped off at the Adelaide St. intersection and walked by the candy shop and barber that rented his storefronts. The shops on the western half of the building, where his family had taken a chance in 1880, were vacant. The saloon business was tough during Prohibition. If you were well connected, it was easy to get your hands on good alcohol, but it was still illegal to drink in public. You had to go to a blind pig or a speakeasy where the drinks were poured in the shadows.

The Grand Opera House had been his first love, his life, and Ambrose couldn’t leave it behind. There were still a few details to square away, and he had finagled a deal with Trans-Canada: he would keep this office, halfway up the first-floor stairs, for the time being.

The Dumbells were on the marquee tonight, in the middle of a two-week engagement with their Biff! Bing! Bang! show, with tickets selling from 25 cents to one dollar. The Dumbells were a group of soldiers who had been a smash hit on the Western Front, performing skits and songs, often in drag, about life in the trenches with a bittersweet, comic tone that played well with men who needed a laugh — like “Oh, It’s a Lovely War” and “Those Wild, Wild Women Are Making a Wild Man of Me.”

They had taken the edge off the war, and they helped take the edge off the memories. Ambrose had been the one who had told them they needed to invest in a bigger cast if they wanted to tour Canada. Their reworked show premiered at his London theatre earlier that year. It was a sellout, and Small called from Toronto during the first act and stayed on the phone for the entire show, listening to the thunderous applause.

As the theatre staff prepared for that evening’s performance, Ambrose popped out for a shave around 1 p.m. Everyone in the barbershop knew about the deal because he mentioned there might be a case of whisky in it for them to celebrate. “I have the million right here,” Small said, patting his coat pocket as the barber expertly ran the sharp blade against the stubble on his neck.

The rest of the afternoon passed pleasantly enough. There was lunch with his lawyer and Theresa, and then he walked Theresa to the nearby orphans home, promising he would be home for dinner.

At some point that day, Ambrose walked into the Dominion Bank and deposited his $1 million cheque in his personal savings account. Had he told Theresa he would put the money in their joint account so they both could access the funds? Was she meant to receive other money? Nobody knew except the Smalls, but Ambrose had grown rich off these kinds of tricks — promising one thing, doing another.

When lawyer Edward Flock dropped by the Grand Opera House at 5 p.m. to pick up his money for helping Ambrose to close the deal, Ambrose was in a good mood, “just like a boy out of school.” Ambrose invited Flock for dinner at his home in Rosedale — the two of them could get a taxi together, he suggested — but Flock had to catch the 6 p.m. train back to London.

Flock gave his regrets and left Ambrose at 5:30 p.m., climbing down the creaking stairs into the lobby and then into the cold. It would be the last confirmed sighting of Ambrose Small.

***

When Ambrose didn’t come home for dinner that night, a worried Theresa left Rosedale to find him. She darted about the city like a pinball, travelling on foot and by streetcar, stopping by the homes of her sisters, making telephone calls to her husband’s associates, trying to figure out where Ambrose was, if anybody had heard from him.

Meanwhile, Alfred Elson, the caretaker of a girls school on Bloor St., was enjoying the crisp night as he flooded the lawn for the skating rink. Toronto’s skating rinks were popular spots in the winter: You met your friends, you wore a fashionable winter outfit, you lined up a few laps with a handsome boy. For a few days now, it had been cold enough for a scarf, so Elson stood on the plateau above the Rosedale Ravine and turned on the hose.

It was a bright night, and a dusting of snow glittered on the ground. Downtown, Hamlet cast a spell over the crowd at the Royal Alex, Charlie Chaplin’s plasticine face was sending audiences into hysterics at the moving picture houses, and Follies of Pleasure was titillating the crowd that went in for that kind of thing at the Star Theatre. From the edge of Bloor St., where the city dipped abruptly into a forested ravine, Elson saw a car driving along the road below, on the way to the dump. The car stopped under a lamppost and four men dragged a rather cumbersome lump from the car. Elson was curious, but a fence blocked most of his view. When they returned to the car emptyhanded, he went back to flooding his rink.

Excerpted from The Missing Millionaire by Katie Daubs. Copyright © 2019 by Katie Daubs. Published by McClelland & Stewart, a division of Penguin Random House Canada Limited. Reproduced by arrangement with the Publisher. All rights reserved. Sources include archival files and various Toronto newspapers. Full citations can be found in the book.

The Missing Millionaire

Correction — Sept. 7, 2019: This article has been updated to correct the date of the Armistice to Nov. 11, 1918.