Hotel Delmonico, 1937.

Built in 1927, this 32-story neo-Renaissance building struggled through its early years, cycling through owners and names. First called the Cromwell Arms, the building became the Delmonico in September 1928 and was sold by its owners in foreclosure less than six months later, The name stuck, though. The hotel changed a hands a few more times, becoming a hangout for the social elite in the 1960s and a luxury apartment building in the mid 1970s. The building, once again a hotel, was purchased in 2001 by Donald Trump for $115 million. Today the building is a condo called the Trump Park Avenue.