The Disappearance of Ambrose Small | The Canadian Encyclopedia


The Disappearance of Ambrose Small

On 2 December 1919, a day after completing a million-dollar business transaction in Toronto, entertainment tycoon Ambrose Small mysteriously disappeared. Despite an international search, no trace of him was ever found. Police suspected foul play and investigated Small’s wife and personal secretary. However, neither the police nor a private investigator uncovered any evidence connecting them to his disappearance. The Ambrose Small case remains one of Canada’s most perplexing and legendary unsolved mysteries.

Ambrose Small


Ambrose Joseph Small was born in 1866 in Bradford, Canada West (now Ontario), to Daniel and Ellen Small. By 1876 Small’s family had moved to Toronto, where Daniel became manager of the Grand Hotel by 1880. Next door to the hotel was the Grand Opera House, a prestigious establishment that presented the best shows coming out of New York. In 1884, the teenaged Small began working at the bar of the Grand Hotel and quickly caught the attention of the manager of the adjacent Grand Opera House. He started working there as an usher and quickly rose through the ranks to become treasurer. He was also involved in an illegal bookmaking operation, taking bets on horse races.

Ambrose Small

Small’s mother died in 1887. In 1889, Small had a quarrel with Grand Opera House manager Oliver B. Sheppard, after which he went to work for the Toronto Opera House, a venue for vaudeville and popular melodrama on the touring circuits controlled from New York and Montreal. While Small learned the intricacies of the business and was eventually promoted to manager, his father married Josephine Kormann, daughter of wealthy beer baron Ignatius Kormann.

Small was an ambitious and shrewd businessman. Within a few years he had accumulated enough capital to buy the mortgage on the Grand Opera House. Most sources claim he eventually fired Sheppard, though others state Sheppard had already left the Grand to manage another theatre before Small took control.

Grand Opera House
Adelaide Street, south side, looking east from Bay Street, Toronto, 1924.

Small fought his way to the forefront of Ontario’s highly competitive theatrical business. He understood public tastes in entertainment and readily adapted to change. He went into partnership with Detroit theatre mogul Clark J. Whitney, who controlled a major circuit in Ontario. When Whitney died in 1902, Small bought up theatres in Peterborough, Hamilton, St. Thomas, Kingston and other communities across Ontario. He leased others. They all depended on him for booking shows because he had taken control from the New York syndicates. Small ran an empire of 34 theatres, half of which were outside Ontario. Stars of the stage who wanted to perform in those theatres had to deal with Small.

Marriage and Reputation

In 1902, Ambrose Small married Theresa Kormann, his stepmother’s younger sister. Their combined financial assets made the couple very rich. But aside from their mutual desire to accumulate more wealth, they had little in common. Theresa was a devout Roman Catholic with a great interest in the arts and charitable works. She spoke frequently at women’s societies about her extensive travels and could read in eight languages. Though the two vacationed together often, Small was a gambler and womanizer who preferred racetracks in the United States to shopping holidays in Europe. He had a secret chamber built in the Grand Opera House for his trysts with chorus girls — of which his wife was aware. Theresa even found a bundle of love letters Small’s mistress had written to him. The Smalls lived in an opulent mansion in Toronto’s affluent Rosedale district, but they slept in separate bedrooms. They had no children.

Small gained a reputation for being ruthless and unscrupulous. He allegedly enjoyed finding means of cheating associates. He planted business contracts with clauses he called “jokers” that worked to his financial advantage. Small was also suspected of using his influence to “fix” horse races. His quarrelsome nature and underhanded methods made him widely hated. Toronto journalist Hector Charlesworth, who knew Small personally, wrote in his 1928 book More Candid Chronicles: “If I heard once, I heard a score of times the ominous words: ‘Somebody will get Amby some day.’”

Theresa Small

The Million-Dollar Deal

By 1919, live theatre was in decline due to the growing popularity of motion pictures. Ambrose Small decided to get out of the business. He struck a deal to sell his chain of theatres to Trans-Canada Theatres Limited of Montreal for $1.7 million. One million dollars was payable upon signing the document of sale and the rest would be paid by installments.

On 1 December 1919, at the law offices of Osler, Hoskin and Harcourt in the Dominion Bank building on King Street, Small, Theresa and attorney E.W.M. Flock met Trans-Canada Theatres representative William Shaughnessy to sign over the theatres. They received a cheque for $1 million. The cheque was deposited at the Dominion Bank the next morning, though sources differ as to whether it was Theresa who deposited it into their shared account, or Small who deposited it in his personal account.

The exact timeline of 2 December, the day of Small’s disappearance, varies according to the source. He reportedly made several expensive purchases for his wife, including a Cadillac, jewellery and a fur coat. He had lunch with Flock and Theresa, walked Theresa to a nearby orphanage where she volunteered, then returned to his office at the Grand Opera House. There, he again met with Flock to clear up some business matters. He invited Flock to dinner, but Flock had to catch a train to London at 6:00 p.m. Flock left the office at 5:30 p.m. He was the last person known for certain to have seen Small. After that, Ambrose Small vanished.

Ambrose Small Missing Person Poster
Missing person poster issued by the Toronto police in 1928. Small had been missing since 2 December 1919.

The Search

Two weeks passed before associates of Ambrose Small’s reported him missing to Toronto police. Theresa claimed that she hadn’t reported his disappearance out of fear of a scandal. “I believe my Amby is in the hands of a designing woman, somewhere, and will come back,” she said. Nonetheless, she offered a $500 reward for information on his whereabouts and had circulars distributed across Canada and the United States.

Small hadn’t packed any suitcases and wasn’t carrying much cash. Police found no evidence of him paying for transportation or accommodation by cheque. Police made inquiries at his usual haunts, but Small could not be found in any of them. They interviewed his mistress, Clara Smith, but she claimed to know nothing of his whereabouts and had been living in Minneapolis at the time of his disappearance. A story that he’d been kidnapped by New York gangsters proved groundless.

When Theresa increased the reward for information to $50,000, the Small story became an international sensation. Reports of alleged “sightings” came from as far away as Mexico. Self-professed clairvoyants offered their services. In New York City, reporters asked visitor Sir Arthur Conan Doyle, creator of Sherlock Holmes, if he was going to help the Canadian police find Small. There were so many false claims that the attorney general kept a folder for them labelled “letters from cranks.” Rumours circulated that Small was in hiding, that he was wandering around somewhere with amnesia; but the speculation that had the greatest possibility of being true was the one that he’d been murdered and his body disposed of.

Ambrose Small Case
Sequence of events illustration from The Milwaukee Journal, 28 September 1932.

The Suspects

The first principal suspect was James “Jack” Doughty, Ambrose Small’s personal secretary. Doughty had worked for Small for years and had often complained about his tiny salary. Doughty disappeared soon after Small did, along with about $100,000 in Victory Bonds from Small’s safety deposit box in the Dominion Bank. Police learned from informants that Doughty had spoken of plots to kidnap or murder Small. Doughty was eventually arrested in Oregon and charged with theft and conspiracy to kidnap Small. He was represented by Clara Brett Martin, the first female lawyer in the British Empire, as well as a prominent attorney named Isidore Hellmuth. He was convicted of theft for the bonds, though he argued he had power of attorney over the security deposit box and had always meant to return them. The kidnapping charges were dropped due to lack of evidence.

Small’s sisters, Gertrude and Florence, believed Theresa had conspired to have him murdered. They hired a muckraking private detective named Patrick Sullivan, who failed to find any trace of Small. He published lurid tabloids accusing everyone from the Catholic Church to the police of involvement in a cover-up and was embroiled in libel and obscenity cases as a result of his public allegations. The police dug up the basements of the Small mansion and the Grand Opera House, as well as a ravine in Rosedale, but found nothing.

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Aftermath and Legacy

In 1923, the Supreme Court of Ontario declared Ambrose Small officially dead and upheld his will, which left most of his estate to Theresa. She died in 1935, leaving the bulk of the estate to Catholic charities, though much of it was owed in back taxes. The Toronto police officially closed the Small case in 1960.

Speculation over Small’s fate has continued, and the case has been the subject of magazine articles, books, paintings and a 2022 play at the Grand Theatre in London, Ontario, once one of Small’s theatres. In Twenty Mortal Murders (1978), Canadian author Orlo Miller made a case for Small’s body being incinerated in the furnace of the Grand Theatre. In The Missing Millionaire (2019), journalist Katie Daubs proposed that the most likely theory was that of Inspector Edward Hammond, of the Ontario Provincial Police. Hammond, who was one of the original investigators on the case, believed that Doughty had killed Small and Theresa had covered for him. The most notable fictional treatment is in Canadian author Michael Ondaatje’s acclaimed 1987 novel, In the Skin of a Lion. The Small case remains an iconic Canadian mystery.

Theresa Small
Photo taken 28 April 1924.