Windsor Hotel, March 17, 1899.

The Hotel, despite being what some considered to far uptown for success, was very popular and profitable. Alas the owner of the Windsor, John T. Daly owed a large mortgage and substantial constructions debts. When the family whose land the building was located on began foreclosing proceedings, the owner hanged himself. During the 1880s and 1890s the hotel became a popular location for political, financial, and diplomatic wheeling and dealing.

On St. Patrick's Day, 1899, as thousands of revelers streamed by the hotel for the annual parade, a guest on a top floor lit a cigar and did not proper extinguish the match. It ignited a curtain and the cigar smoker exited the building without notifying anyone. The fire spread extremely fast and soon the entire building was engulfed. Despite their best effort to rescue patrons, the firefighters were pushed back by the heat and were forced to watch as people jumped from windows to escape the flames. Some firefighters arrived in their dress blues directly from the parade route. They attempted to keep the fire from spreading to nearby buildings by hosing them down, to some small success.

The building was largely collapsed by 4:30pm, just an hour after the blaze started. The still burning ruins took days to cool down enough for a thorough search of the building. In the end more than 90 people were killed.