The Mysterious Vanishing of Ambrose Small, the Lost Tycoon

Theresa Small clung to a sliver of hope that the reports were false. It was the summer of 1921, and her husband, Ambrose Small, a man of considerable wealth and prominence across Canada, had been missing for almost two years. His sudden and unexplained disappearance had captivated the nation, dominating headlines with its sensational nature.

Two men from Des Moines, Iowa, now asserted they had located Small. However, the once-powerful businessman was in a dire state: he had lost both legs, was nearly unresponsive, and could only mutter four words—train, from Omaha, and a name, Doughty.

As Theresa awaited confirmation, her emotions were undoubtedly conflicted. Part of her longed for closure, while another part recoiled at the thought of her husband enduring such a grim fate. The circumstances were stranger than fiction: in late 1919, Small had cashed a $1 million check—equivalent to roughly $18 million today—after liquidating much of his business. Mere hours later, he had disappeared, leaving the fortune untouched and sparking a mystery that baffled investigators.

The situation defied explanation. Equally puzzling was Theresa’s delay in reporting his disappearance, waiting weeks before taking action. Efforts to find Small included unconventional methods like telepathy, alongside rumors of hidden hideouts, mysterious messages, and alleged kidnapping schemes orchestrated by his staff. Even Sir Arthur Conan Doyle, the renowned author behind Sherlock Holmes, was drawn into the mystery. Ambrose Small’s vanishing became Canada’s most captivating true-crime story of the 1920s. Perhaps the answers lay in Des Moines.

Theresa Small did the only thing she could. She remained by the telephone, anxiously awaiting further details about the legless man and what he might reveal.

A Taste for the Theatrical

Ambrose Small was neither a visionary nor a trailblazer. Instead, he had a sharp business acumen, particularly in the management and operation of theaters across Ontario. His venues hosted a variety of stage productions. If you were looking for live entertainment in the area, chances were high you’d find yourself in one of Small’s establishments, possibly even encountering the man himself—a slender, middle-aged businessman with a thick mustache and an intense gaze.

Small’s journey to success started humbly as an usher at Toronto’s Grand Opera House. Dissatisfied with limited growth prospects and clashing with his manager, he moved to the Toronto Opera House, where he quickly rose to the position of manager. His success there enabled him to purchase the Grand Opera House outright, and his former boss was promptly dismissed under his new leadership.

By 1919, Small’s portfolio had expanded to over 30 venues in Ontario, and he managed bookings for numerous others. Despite this achievement, Small recognized the growing threat posed by the rise of movie theaters across North America. Compounding the issue, the 1918 flu pandemic had compelled widespread theater closures. Sensing the right moment to step away, he struck a deal with Trans-Canada Theaters Limited, selling all his theaters for $1.7 million—approximately $30 million today. This move marked both an acknowledgment of the changing entertainment landscape and a well-earned reward for his decades of hard work.

On December 2, 1919, Small and his wife Theresa left their Toronto residence to attend to separate errands. They planned to meet later with his lawyer, E.W.M. Flock, at Small’s Grand Opera House office. Trans-Canada had issued a $1 million check the previous day, which Small deposited at his bank. Afterward, the couple visited an orphanage where Theresa volunteered. As they said their goodbyes, Small assured her he would be home by 6 p.m. for dinner.

Small then went back to his office for another meeting with Flock, which continued until around 5:30 p.m.

Small was expected home in just half an hour. He never made it.

While most would panic at their spouse’s sudden absence, Theresa remained calm. Aware of her husband’s infidelity, she assumed his failure to return was due to an affair. Likely feeling humiliated, she chose not to raise the alarm.

Others, however, quickly noticed Small’s disappearance. As weeks passed, local newspapers began covering the story. George Driscoli, a Trans-Canada executive involved in the theater acquisition, was among those questioned. He appeared unconcerned.

“It’s been exactly three weeks since Mr. Small finalized the deal transferring his theater interests to us,” Driscoli remarked. “He mentioned he planned to take an extended break. After years of hard work and the stress of managing his vast business, he felt it was the perfect time for a vacation, far removed from the theater world and his other obligations.” Driscoli speculated Small might be in a remote wilderness area or perhaps traveling through Europe.

Some reports suggested Theresa claimed her husband was recovering from a nervous breakdown and simply needed rest. In reality, Theresa had no clue about his whereabouts. This uncertainty prompted James Cowan, manager of the Grand Opera House, to contact the police. Detective Austin Mitchell was assigned to the case, which would become one of the most bizarre investigations of his career.

Bonded

Mitchell tried to trace Small’s movements beyond his meeting with Flock on the evening of December 2. Two newspaper delivery boys reported seeing him, while another witness claimed Small entered a hotel near the Grand Opera House. However, Mitchell discovered their accounts were unclear about whether the sightings occurred on December 2 or the previous night. Another individual insisted he witnessed four men struggling to bury something heavy near a ravine, but no evidence was ever found.

It wasn’t far-fetched to think Small had crossed someone. Beyond his business acumen, he was known for gambling, possibly fixing horse races, and his womanizing—rumors even suggested he had a secret room in the Grand Opera House for rendezvous with actresses and dancers. Any of these activities could have provoked someone to target him, whether a scorned lover or someone involved in illegal dealings.

This theory gained traction when Mitchell uncovered a wire message sent from Ontario to New York that stated: “Hold Small until tomorrow morning.” The implication of a kidnapping plot was clear, but Mitchell found no further evidence to support it.

Mitchell was also aware of another disappearance tied to the Small case. A month after Small vanished, his employee, John Doughty, fled town. Mitchell learned that Doughty had taken $105,000 in bonds belonging to Small. Even more incriminating: Doughty had withdrawn the bonds from the bank on the morning of Small’s disappearance.

A $15,000 reward was announced for information leading to Doughty’s arrest. In late 1920, he was found working at an Oregon paper mill under the name Charles Cooper. The bonds were recovered from his sister’s home. Doughty claimed Small had instructed him to retrieve the bonds from the bank’s safety deposit box and hold onto them. After that, he said, Small disappeared.

When questioned about Small, Doughty gave a puzzling reply. “I’d like to assist you,” he said. “You’ve treated me fairly, but my lawyer has advised me not to speak about the case.”

Mitchell discovered that Doughty had floated the idea of kidnapping Small to two colleagues. While this seemed promising, it wasn’t enough for a court case. No concrete evidence of a kidnapping emerged. Regarding the bonds, Doughty claimed he had power of attorney, making their removal legal. He fled, he explained, because possessing the bonds made him a prime suspect in Small’s disappearance.

A jury convicted him of theft but found no evidence linking him to a kidnapping scheme, a charge prosecutors never pursued in court. He was sentenced to six years behind bars.

With Doughty refusing or unable to provide further details, the investigation began to fall apart. At one point, a journalist handed Small’s case file to Sir Arthur Conan Doyle, the creator of Sherlock Holmes, hoping the famed author might solve the mystery. Doyle was polite but had no genuine interest in delving into the matter.

Reports of Small sightings were rampant. Blackstone, a renowned magician, claimed he saw Small gambling in Mexico after his disappearance. However, it wasn’t until the call from Des Moines in August 1921 that Theresa felt there was a real chance her husband had been located.

At least, most of him.

A Step Forward

Frank Harty and John Brophy, former Des Moines police officers, had transitioned to private detective work. They came forward with an astonishing story.

In their custody was a legless man who could only speak a few words. They were convinced he was Ambrose Small, citing his striking resemblance to the newspaper photos of the missing millionaire. When asked his name, he mumbled something resembling “Doughty,” likely referencing John Doughty, the dubious employee who had stolen the bonds.

Mitchell and other officials were eager to see the man. Theresa was informed that this disfigured individual might indeed be Small—altered, but possibly her husband.

That hope was short-lived. The man was not Ambrose Small but Charles Daughtery, a drifter whose legs had been severely injured after jumping from a train. When questioned, he correctly stated his name, but Daughtery was misheard as Doughty. At 33, he was also significantly younger than Small.

Whether the detectives truly believed he was Small or were attempting to claim a $50,000 reward remains unclear. Regardless, it was another setback for Mitchell and Theresa. Not only had she lost her husband, but her inheritance was also contested by Small’s sisters, Gertrude and Florence. (Theresa eventually won the case, though the Small estate never recovered the $700,000 owed by Trans-Canada, which had gone bankrupt.)

No Breakthrough in Small’s Case

The lack of concrete evidence opened the door for countless theories. In 1928, Maximilian Langsner, a Viennese criminologist, claimed he could solve the mystery using “mental telepathy and thought analysis” and even produce Small’s skeleton. He briefly gained the interest of Small’s sisters and planned to excavate a dump where a witness claimed to have seen something buried. However, Langsner failed to deliver any meaningful insights.

In 1930, Arthur Weatherup, Small’s longtime barber, insisted that an amnesiac who died in a hospital was actually Ambrose Small. Police quickly dismissed the claim. Sixteen years later, the site of the Grand Opera House was dug up, with some speculating it might hide secrets, including a body. Once again, nothing was found.

Small’s vanishing act became a cultural reference in Canada. If someone was digging, they might jokingly be asked if they were searching for him. The one person who might have known the truth, John Doughty, passed away in 1949 without revealing any further details. However, the fact that he took $105,000 of Small’s money on the day of his disappearance is a suspicious coincidence.

After his release from prison, Doughty remained tight-lipped. “My past is a closed chapter,” he stated. “I have no comment about Mr. Small or anything related to him.”

The delay in reporting Small missing further complicated matters, likely fueling the resentment of Small’s sisters, Gertrude and Florence. After Theresa’s death in 1935, they presented a note they claimed was her confession to murdering her husband. The letter alleged Small’s body was burned in a furnace, with the ashes buried in a dump. This conveniently positioned them to inherit her estate instead of it going to charity. A judge dismissed the confession as a forgery.

The idea that Small would willingly leave his affluent life, with a substantial bank account, remains baffling. Given the total absence of credible leads, it’s probable he met a violent fate. As a theater magnate, it’s eerily fitting that Small’s final act was the most dramatic of all.