Many prominent families lived at 14 Madison Ave.

By Michael Mastromatteo

Nearly 100 years after they were first constructed, three old mansions at 14-18 Madison Ave.  gained a new lease on life.

In 1983, after surviving the “rooming house malaise” of the 1960s, the houses evolved into the Madison Pub, a popular fixture in the Annex.

In addition to the pub itself, the “Mad” now includes restaurants, a niche boutique hotel, and another hotel property in Puerto Vallarta, Mexico.

Although the pub today includes 14, 16 and 18 Madison, this month’s “If walls could talk” story will focus on number 14.

One of the first owners of the property was John Bertram, who in 1895, operated a wholesale hardware business at 76 Wellington St. W. Betram may have been quite a mover and shaker in late 19th century Toronto. The name John Bertram is associated with boat design and Toronto Harbour operations of the day.

There was at least one happy celebration at 14 Madison during the Bertram era. On June 16, 1897, the Toronto Daily Star reported the marriage of Bertram’s daughter Kate to a Thomas Bradshaw. The happy couple later took up residence on Lauder Street.

Bertram and family resided at 14 Madison until about 1900 when the home was taken over by George Kerr, a lawyer with the old Toronto firm Kerr, Bell & Shaw. 

As with many Annex homes, the Kerrs needed cooks, servants, and domestics. A Toronto Daily Star classified ad from Sept. 25, 1905 reads: “General servant, small family, best wages, apply evenings, Mrs. Kerr, 14 Madison Ave.”

In 1915, the house was taken over by Dr. Benjamin P. Watson who resided there with his wife Angele, daughter Monique, and son David, for the next six years. In August of 1919, Mrs. Watson advertised for “an experienced cook wanted – at once.” Just three months earlier, Mrs. Watson advertised for “a Nursemaid for child of 10 months. Apply with references.”

The Toronto Daily Star of June 16, 1917 made mention of Watson’s marriage to the former Angele Hamendt of Belgium at St. Andrew’s Church on King Street West. 

Dr. Watson certainly left a legacy. A New York Times obituary dated August 8, 1976, reported his passing at age 96. Dr. Watson was born on Jan. 4, 1880, in Anstruther, Scotland. He attended Edinburgh University and received his medical degree in 1905. A tall, distinguished?looking man, he was appointed professor of Obstetrics and Gynecology at the University of Toronto in 1912, a job he held for 10 years, with time out for service in the First World War. He was a captain in the medical corps of the Canadian Army and served in Macedonia, Greece.

In 1949, he became president of the New York Academy of Medicine. Dr. Watson was a professor at Columbia and became professor emeritus in 1960. He continued to practice as a surgeon until well into his 80s.

Before moving forward, here’s an interesting anecdote from the house at 18 Madison, now the site of the Madison Pub’s boutique hotel.

Early in the 20th century, 18 Madison was home to Commanding Officer John Irvine Davidson who, in 1905, founded the renowned 48th Highlanders Regiment. Baby boomers will certainly remember that for many years, the 48th Highlander’s pipe band performed God Save the King/Queen and O Canada on opening night for Leafs games at Maple Leaf Gardens.

Commanding Officer John Davidson died April 28, 1910. His widow Mary, lived on at 18 Madison from 1914 until her death on April 17, 1930. Mary, the daughter of Robert Hay (MP Centre Toronto), was active in Toronto’s social circles and volunteered at the Red Cross, the Hospital for Sick Children and a number of British Empire societies.

Getting back to 14 Madison. From 1922-1934, the building housed the Alpha Kappa Kappa (AKK) medical fraternity of the University of Toronto’s medical school. The housekeeper/den mother was a Margaret (or Mary) Fortier, who must have had a lot of patience. One can wonder if a Toronto medical fraternity in the 1920s and early ’30s resembled the Animal House frat from the John Belushi movie.

The Statten family, Waldermar and wife Helen, resided at 14 Madison from 1936 to 1938. They might have been the first family to begin letting rooms. An assortment of Toronto Daily Star ads from 1936-37 offered “double and single rooms, fireplace seat, bath floor, excellent meals.”

From 1939 until 1970, the home sheltered one Annie Millar. Try as we might, we couldn’t find any information on Annie and her family, despite her 31 years of residency. Oh where have you gone Annie? What are the stories you and your listening walls might have told?

With Millar’s departure in 1970, the story of 14 Madison gets a little sketchy. In 1975, an A. Milne resided there, and around 1980, the home was the business address of Lawson and Jones (possibly a printing company) and an enterprise known as Cobett-Jenner-Wasylow International. 

This brings us to 1983 when Dave and Isabel Manore turned an aging Victorian mansion into what is today’s four-house strong Madison Pub and hotel complex. “We’ve been part of the city’s social fabric for decades,” says the Madison website. 

Let’s hope today’s walls—whether original or those installed during extensive renovations—are still paying attention to what goes on within.

READ MORE:

• IF THESE WALLS COULD TALK: 351 Palmerston Blvd. (Oct./Nov. 2025)
• HISTORY: If these walls could talk (Sept. 2025)