The first Madison Square Garden, ca. 1891. Originally a station for the Cornelius Vanderbilt-owned New York & Harlem Rail Road, P.T. Barnum converted the terminal space into the Great Roman Hippodrome Arena in 1871. It became Gilmore's Garden, named for the entertainment impersario Patrick Gilmore, in 1876. The following year, the area hosted the first edition of the competition that would become the Westminster Kennel Club Dog Show. Following Vanderbilt's death, William Kissam Vanderbilt assumed control of the site, changing the name to Madison Square Garden. In 1889, the younger Vanderbilt sold the aging venue to a group of Gilded Age industrialists who hired architect Stanford White to design a new Garden on the same site.

New York Life Insurance, 1929. Between 1879 and 1925 this plot at Madison Avenue and 26th Street was home to the first two incarnations of Madison Square Garden. MSG II (by famed architect Stanford White) was never a great financial success. In 1925, the New York Life Insurance Company who owned the land decided to demolish the Garden for their new headquarters. Completed in 1928, the New York Life Building stands 40-stories-tall and is topped by a gleaming gilded pyramidal roof. While its ornament is solidly Gothic Revival, its massing and shape are distinctly more Moderne.

This house, which attempted to re-create the glories of Second Empire Paris, was built by Leonard W. Jerome as the American Jockey Club, complete with stables and a small private theatre. It later became the University Club and then the Manhattan Club after that. Though it was given landmark status, it was torn down in 1967 when a buyer couldn't be found. Jerome's grandson, child of his daughter and her husband Lord Randolph Churchill, was the famed Winston Churchill.

Madison Square Garden (second iteration), 1903. This building on the corner of Madison Avenue and 26th Street was the second on the site to bear the name Madison Square Garden. The first, built by William K. Vanderbilt in 1879, was a drafty structure that presented athletic attractions, most notably boxing matches featuring John L. Sullivan. Unable to make a profit, Vanderbilt razed the building in 1889, after which the Horse Show Association gained control of the site and hired Stanford White of the renowned firm McKim, Mead, and White to design a new structure. White's Madison Square Garden was a Moorish fantasy that cost three million dollars, was the second-tallest building in New York, and boasted an 8,000-seat auditorium that was the largest in the United States. (It also featured a roof garden where White would meet his end in 1906, shot by Harry Thaw on suspicion of having seduced Thaw's young wife, Evelyn Nesbit.) The second Madison Square Garden, which presented horse shows, dog shows, bicycle races, boxing matches, and the Democratic National Convention of 1924, became profitable once promoter Tex Rickard leased the building, but it, too, was razed in 1925 to make way for the new headquarters of New York Life Insurance Company. Rickard kept the name Madison Square Garden but moved the sporting and entertainment facility across town and uptown to Eighth Avenue, first at 50th Street and then to its current location at 32nd Street.

Though many may not know it, the current Madison Square Garden is, in fact, the fourth Madison Square Garden!

ca. 1966 The Jerome Mansion (pictured here in itself final days) was once home to Leonard Jerome, a millionaire speculator, and financier. Jerome was one of the wealthiest men in New York, making and losing several fortunes over the years. A dashing figure, he yachted with William Vanderbilt, went on hunting trips with Buffalo Bill, and defended the New York Times with a Gatling gun during the Draft Riots. A society man, Jerome founded the famous Coney Island Jockey Club and funded many of the city's early opera houses. It was fitting then that he would have a mansion to match his verve. Jerome had no interest in building a modest home, hiring the English architect Thomas Jackson to build what would be, upon its completion in 1859, one of the biggest and most expensive residences in the city. Designed in the Second Empire style, the Jerome Mansion was six stories high with a mansard roof. While the old money built subtle brownstone mansions, the Jerome Mansion was built to dazzle. Its first two stories were clad in limestone, with the upper stories made of brick and contrasting stone. The interiors were lavishly decorated to impress all that entered. The amenities of the house included: a bowling alley, a library, a trophy room, an art gallery, a billiard room, and a bar (to name but a few!) Decorated in white and gold, the ballroom was unconventionally located over adjoining stables. However, it was still quite a sight, boasting two fountains: one that spouted champagne and another that spouted cologne! In between the stables and the main house, Jerome built a theater that could reportedly hold six hundred people. Even the stables were fitted with stained glass windows. The Jeromes were fervent entertainers with the height of society passing through their doors. All manner of fetes, buisness meetings, and celebrations occurred under Jerome's roof. One such gathering affects us to this day, on November 23, 1869, a meeting took place here that founded the Metropolitan Museum of Art. However, the Jerome family would move to Brooklyn less than ten years after it was built and the Jerome Mansion was leased to the Union League Club. A prestigious blue blood club born out of the civil war, the Union League began expensive renovations and added a seventh floor. It would be the first of a series of clubs to call the mansion home. Following the Union League, the University Club and Manhattan Club would both inhabit the Jerome Mansion in 1883 and 1899 respectively. It was during the Manhattan Club's tenure in the Jerome Mansion that the Manhattan Cocktail was invented at its bar. Having leased it for years, The Manhattan Club eventually purchased the mansion from the Jerome Estate in 1964, a year before it would be landmarked. However, with membership declining, the Manhattan Club wished to sell the mansion to pay down its debts. Filing suit, the Manhattan Club was able to prove they didn't have buyers and, in 1967, it was tragically demolished.

The gilded statue of Diana, Goddess of the Hunt, adorned the tower of Madison Square Garden and held watch over New York City for over three decades. She is arguably the most famous and recognizable work by sculptor Augustus Saint-Gaudens.