2015 marks the 50th anniversary of the New York City landmarks law, which created and empowered the Landmarks Preservation Commission to designate worthy individual landmarks, interior landmarks, and historic districts to save them from the wrecking ball. But there were many fine historic structures completed before 1965 that, for one reason or another, didn't earn protectionor earn it in time. With the help of Tom Miller and his extraordinarily thorough Daytonian in Manhattan blog, which every day offers up a detailed history of a Manhattan building, here are eight of these forgotten architectural gems. Side-by-side, note the incredibly different buildings that now stand in their stead. Sure, there are other prominent ones, but these were picked for a mix of provenance, significance, aesthetics, and contrast between past and present.









[Credits: NYPL, Google Maps.]

House of Mansions

42nd Street and Fifth Avenue

Commissioned by carpet manufacturer George Higgins and completed in 1856 by architect Andrew Jackson Davis, this castle-like structure was actually 11 residences in one. It was located directly across from the Croton Distributing Reservoir, which is now the New York Public Library. Higgins concept of mansions-within-a-mansion was a little too ahead of its time and didn't make a profit. In 1860, it was purchased by the Rutgers Female Institute to become a new campus. However, when that organization turned into a genuine college, the space was no longer adequate and Rutgers moved. The property changed hands several times until French-born manufactuer August Pottier bought it in 1883 and had it demolished.









[Credits: Palatial Homes in the City of New York and the Dwellers Therein, Google Maps.]

The Jennings-McCullogh Mansions

39th Street and Park Avenue

Vermont natives Laura Hall Park and her sister Eliza Hall Park were very closeso close that when they married Frederic Beach Jennings and John Griffith McCullough (who had already been California Attorney General), respectively, they moved in together in Manhattan. Sometime around 1891, they constructed two mansions at the northwest corner of Park Avenue and East 39th Street. Designed by architect J. Lawrence Aspinwall, Laura got the southern half, Eliza the northern. Eventually, left widowed, they abandoned their mansions, and the Princeton Club purchased the property in 1921. The club joined the two mansions internally and remained there until 1963, when it was demolished to make way for the 41-story office tower now known as 90 Park Avenue.









[Credits: Museum of the City of New York, Google Maps.]

H.O. Havemeyer Mansion

66th Street and Fifth Avenue

Henry Osborne Havemeyer was the eighth of nine children and had no formal education beyond age eight. (A fight with school principal turned him off it for good.) That didn't hold him back. By age 15, he had joined his family's sugar refinery business, now called Havemeyers & Elder since his brother Theodore had partnered with his son-in-law, J. Lawrence Elder. Henry married Elder's sister, Mary Louise, in 1870, though they divorced in 1882. A year later, he married his ex-wife's niece, Louisine Waldron Elder. In 1889, one year after the birth of their third child, they planned to build a new family home and purchased the property on the northeast corner of Fifth Avenue and East 66th Street. They commissioned Charles Coolidge Haight to design it, and construction began that year. The rooms were decorated by Louis Comfort Tiffany (yes, that Tiffany) and Samuel Colman. Havemeyer, who became known as the "Sugar King," lived there until his death in 1907. The home remained with the family (despite a threat by some youths to blow it up unless a ransom was paid) until Louisine's death in 1929. The following year, it was announced that the property had been leased, and the mansion would be torn down.









[Credits: Museum of the City of New York, Google Maps.]

Emilie Grigsby House

67th Street and Park Avenue

Susan Grigsby was widowed without a considerable estate. So, in order to keep her children Braxton and Emilie in their respective Catholic schools in Ohio, she opened a brothel in Cincinnati. After graduating (and being informed of her mother's profession), Emilie met her brother's boss, married Chicago financier Charles T. Yerkes. He was taken by the 16-year-old, as was his son Charles Edward Yerkes. This tore the father and son apart. Eventually, the elder Yerkes set his sights on New York and moved to Fifth Avenue, but also had a new home constructed two blocks away, at Park and 67tha home built for Emilie. It was completed in 1898 and replaced a row of brownstones. Yerkes died in 1905. On his deathbed, it was Emilie, not his wife, that he wanted to see. After his death, Emilie would travel to London, making quite a splash on the social scene there, eventually deciding she was done with New York. In 1912, her New York holdings, which included works by Monet and Pissarro, were auctioned off. In 1926, Frederick Ecker of the Metropolitan Life Insurance Company, commissioned architects to design the apartment building that sits there today, with the first three floors having been intended as a 27-room apartment for Virginia Vanderbilt.









[Credits: Library of Congress, Google Maps.]

Murray Hill Hotel

41st Street and Park Avenue

Following the 1871 opening of the Grand Central Depot (which evolved into what we now call Grand Central Terminal), Hugh Smith, part owner of the city's stagecoaches and son of real estate man Peter Smith, realized the train station lacked a convenient hotel. So he bought some land on Park between 40th and 41st, and commissioned architect Stephen Decatur to design the structure, which would be made of brownstone, granite, cast iron, and red brick. Stockbroker Nathan S. Hunting partnered with David I. Hammond, who managed the Hotel Bristol, to lease the Murray Hill Hotel from Smith and its 600 rooms opened in 1884.

It garnered praise from the New York Times and included the latest in ice-making and refrigeration. The hotel would play host to Mark Twain, P.T. Barnum, Jay Gould, "Diamond Jim Brady," and even Presidents Grover Cleveland and William McKinley. It was not without scandal. On Valentine's Day of 1886, a butcher was stabbed by a fellow worker in his shop. Then in 1902, construction on the Park Avenue subway tunnel resulted in an explosion, killing a worker and blowing out every window on two sides of the hotel. Several people in the hotel were also killed, and material damage was significant. There was also a fire in 1904, which destroyed 16 to 20 of the apartments. Hugh Smith's sister lived there until she died in 1906 and, in 1910, it was auctioned to Benjamin L.M. Bates, who had worked his way from assistant night clerk to manager of the hotel. He died in 1935. Though he left the bulk of his estate to his sister Adelaide Roberts, his will left $300 a month to a Helen M. Bates, who had claimed to be Benjamin's wife. He disputed the claim, but left her the money to avoid notoriety. Roberts quickly sold the hotel. It lived on for over a decade.

In 1946, the owners announced plans to demolish the hotel, but the residents sued. A court ruled that they were guests, not residents. But it was all for naught. By 1948, it had been demolished. What sits there now is known as 100 Park Avenue.









[Credits: L'Architecture Americaine, Google Maps.]

Webb and Twombly Houses

54th Street and Fifth Avenue

Eliza Webb and Florence Adele Twombly were two of William Vanderbilt's daughters. (William was Cornelius's son.) Webb was married in 1877 and legend has it her wedding gift was to be a Fifth Avenue mansion, but construction didn't start until 1883 when an accompanying mansion for her sister was added to the plans. They were designed by John B. Snook. The Webb family took no. 680 while the Twombly family took no. 684. Hamilton Twombly would become one of William Vanderbilt's most trusted advisers and a manager at the New York Central Railroad. As for William Seward Webb, he was convinced to give up medicine for finance, eventually becoming head of four railroads. The sisters had to carefully coordinate their social schedules so as not to put guests in the position of deciding which house to visit. There were triumphs and tragedies, including the drowning death of Hamilton Twombly, Jr.

The Webbs put their mansion up for sale in 1913, and John D. Rockefeller stepped in to replace it with a six-story commercial building, though that didn't happen until 1917. Widowed, Florence Adele Twombly stayed put until 1925, when Rockefeller purchased her mansion and replaced it with an extension of his new building, known as the Rockefeller Building. It stood until 1956, when it was replaced by Buchmann Tower.









[Credits: NYPL, Google Maps.]

Grand Opera House

23rd Street and Eighth Avenue

The neighborhood of Chelsea gets its name from the estate of retired British Major Thomas Clarke. The name Chelsea was passed down through his family until it got to Clement Moore. After his 1863 death, parcels of Chelsea were sold off, one of them, at the northwest corner of Eighth and 23rd, going to a man named Samuel Pike. Pike intended to build an opera house there like the one he had built in Cincinnati. His dream was realized in 1869 when Pike's Opera House, a five-story marble-adorned structure, opened. Built for 1,800 people, twice that would squeeze in. But despite staging some of the best opera of the day, it was the Academy of Music on 14th Street that ultimately won over artsy New Yorkers. Pike's Opera House closed within a year.

Railroad man Jay Gould and financier James Fisk bought the house from Pike, established Erie Railway offices, renamed it the Grand Opera House, and changed the entertainment lineup. Fisk was reported to have had his mistress and a neighboring house. Fisk ended up being shot dead in the opera house when a business partner became unhappy with him, apparently something to do with the aforementioned mistress. True success continued to elude the opera house, though it remained intact until RKO commissioned Thomas Lamb Associates to remodel it as a movie theater in 1938. It kept going until 1960, when it was closed for demolition and then gutted by fire. What is there now is a rather disappointing three-story commercial structure.









[Credits: NYPL, Google Maps.]

Working Women's Hotel

33rd Street and Park Avenue

In 1823, Alexander Turney Stewart came to New York from Lisburn, Ireland and opened a small dried goods store with lace and linens he had brought with him. By 1848, his emporium was the largest in the world, with international outposts. He was among the richest men in the country. Known to be generous, he preferred to invest in worthwhile causes rather than just donate his money.

Enter the aftermath of the Civil War. Many war widows were struggling to find lodging that was both affordable and respectable. So, in 1969, Stewart commissioned architect John Kellum, who had designed his store on Broadway, to design a "women's hotel" to house up to 1,500 females working in "day labor." It occupied the full block of Park from 32nd to 33rd, had a large central courtyard, and was done in the French Second Empire style. Stewart's poor health and a financial crisis in 1873 dragged construction on for about eight years.

The hotel finally opened on April 2, 1878. Sadly, neither Stewart nor Kellum lived that long. The Times estimated that nearly 20,000 people had visited the hotel on opening day. Despite elaborate design and decoration and major publicity, Stewart's widow declared the hotel a "complete failure" 54 days after it opened. She cited labor costs, but theories and opinions about the failure abounded. Either way, she shuttered it to make changes and reopen it as a commercial hotel, which happened on June 8.

In 1902, the nearby 71st Regiment Armory caught fire, with embers spreading to the hotel. The hotel had been touted as fireproof, but the exit stairs were padlocked and 21 people died. The hotel kept going. In 1919, the employees walked out. But it wasn't a strike. Think of it more like senior cut day in high school. They just wanted some fun. They planned a party and even invited the hotel's guests. Unfortunately, the clock was ticking and Stewart's dream finally came to an end in 1925, when the building was purchased with the intention of replacing it with a taller commercial structure. What stands there now is 2 Park Avenue, which was built in 1927.

—Evan Bindelglass is a local freelance journalist, photographer, cinephile, and foodie. You can e-mail him, follow him on Twitter @evabin, or check out his personal blog.

· Daytonian in Manhattan [official]

· Looking Back at Manhattan's Lost Gilded Age Mansions [Curbed]

· All Preservation coverage [Curbed]