Remains of the Windsor Hotel, 1899. This photograph is dated one day after the massive Windsor Hotel fire that claimed the lives of more than 90 people. The charred ruins of the building were not demolished immediately and the search for victims went on for nearly a month. Despite suggesting that they would erect a monument to the tragedy's victims, hotel proprietor Warren F. Leland and land owner Elbridge T. Gerry ended up using the site for billboards in the year after the fire. In 1901 a new three-story building, the Windsor Arcade, was constructed and housed luxury shops. It was later demolished in 1910.

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.

Windsor Hotel, ca. 1885. The Windsor Hotel, which occupied the entire blockfront on the east side of Fifth Avenue between 46th and 47th Streets, was hotel for a new kind of neighborhood. Construction on the seven-story hotel began in 1871, the same year the Grand Central Depot opened a few blocks away. The lots on Fifth Avenue between 42nd Street and 50th Street (where St. Patrick's Cathedral would rise in 1878) were being transformed from simple wood-frame structures, open spaces, and natural features like ponds, into a neighborhood of wealthy residents. When the hotel opened in 1873, it catered to this affluent sect. It was referred to in a late 19th century book as “at that time, the most luxurious and aristocratic hostelry in New York.”