It soon became apparent that the first hotel was far too small, and it was demolished in 1905 by new owners, hotelier Fred Sterry, Harry S. Black and German financier Bernhard Beinecke, who envisioned a much larger, new Plaza Hotel, which was designed as an opulent, 19-story, French Renaissance-inspired château-style building by Henry Janeway Hardenbergh.
The new hotel was constructed in 27 months, at a then-unprecedented cost of $12.5 million, up from previous estimates of $8.5 million.
It was opened October 1, 1907; the first guest was Alfred Gwynne Vanderbilt.
When the hotel opened, a room at the Plaza Hotel was only $2.50 per night (the equivalent of $68.6 in 2019).
The hotel proved so popular that a huge, 300-room annex was added along 58th Street from 1920–1921.

Conrad Hilton bought the Plaza Hotel for $7.4 million in October 1943 (equivalent to $109 million in 2019) and spent $6 million (equivalent to $88.7 million in 2019) refurbishing it.
Hilton sold the hotel 10 years later, in 1953, to Boston industrialist A.M. "Sonny" Sonnabend for $16 million.
Hilton sold the Plaza to raise funds for construction of the Beverly Hilton, but immediately leased the Plaza back for two and a half years, and then another four when that lease expired.
Sonnabend became president of the Childs Company, a national restaurant chain, two years later, and Childs purchased the Plaza on November 18, 1955, for $6.2 million in stock (equivalent to $60.4 million in 2019).
Childs had partnered in the development of the neighboring Savoy-Plaza Hotel, (now the site of the General Motors Building).
Sonnabend created the Hotel Corporation of America (HCA) in 1956, to leverage tax losses from Childs.
HCA assumed management of the Plaza from Hilton in January 1960.
HCA changed its name to Sonesta International Hotels in 1970.
Sonesta sold the Plaza to Western International Hotels in 1975 for $25 million (equivalent to $119 million in 2019).
Western International changed its name to Westin Hotels in 1981 and the hotel was renamed soon after, becoming the Westin Plaza.


Westin sold the Plaza to Donald Trump for $390 million on March 27, 1988 (equivalent to $843 million in 2019).
Trump commented on his purchase in a full-page open letter in The New York Times: 
I haven't purchased a building, I have purchased a masterpiece—the Mona Lisa.
For the first time in my life, I have knowingly made a deal that was not economic—for I can never justify the price I paid, no matter how successful the Plaza becomes.

 Trump installed his wife, Ivana Trump, as the hotel's president.
After $50 million in renovations, the hotel was earning a healthy operating income, but not enough to make the payments on its heavy debt load.
Trump made plans to pay off the hotel's debt by selling off many of its units as condominiums.
A deal was instead reached for the Plaza's creditors, a group of banks led by Citibank, to take a 49% stake in the hotel in exchange for forgiveness of $250 million in debt and an interest rate reduction.
The agreement was submitted as a prepackaged bankruptcy in November 1992.

In 1995, CDL Hotels International and Saudi prince Al-Waleed bin Talal purchased a controlling stake in the Plaza in a deal that valued it at $325 million (equivalent to $545 million in 2019).
It soon became apparent that the first hotel was far too small, and it was demolished in 1905 by new owners, hotelier Fred Sterry, Harry S. Black and German financier Bernhard Beinecke, who envisioned a much larger, new Plaza Hotel, which was designed as an opulent, 19-story, French Renaissance-inspired château-style building by Henry Janeway Hardenbergh. The new hotel was constructed in 27 months, at a then-unprecedented cost of $12.5 million, up from previous estimates of $8.5 million. It was opened October 1, 1907; the first guest was Alfred Gwynne Vanderbilt. When the hotel opened, a room at the Plaza Hotel was only $2.50 per night (the equivalent of $68.6 in 2019). The hotel proved so popular that a huge, 300-room annex was added along 58th Street from 1920–1921.
Conrad Hilton bought the Plaza Hotel for $7.4 million in October 1943 (equivalent to $109 million in 2019) and spent $6 million (equivalent to $88.7 million in 2019) refurbishing it. Hilton sold the hotel 10 years later, in 1953, to Boston industrialist A.M. "Sonny" Sonnabend for $16 million. Hilton sold the Plaza to raise funds for construction of the Beverly Hilton, but immediately leased the Plaza back for two and a half years, and then another four when that lease expired. Sonnabend became president of the Childs Company, a national restaurant chain, two years later, and Childs purchased the Plaza on November 18, 1955, for $6.2 million in stock (equivalent to $60.4 million in 2019). Childs had partnered in the development of the neighboring Savoy-Plaza Hotel, (now the site of the General Motors Building). Sonnabend created the Hotel Corporation of America (HCA) in 1956, to leverage tax losses from Childs.HCA assumed management of the Plaza from Hilton in January 1960. HCA changed its name to Sonesta International Hotels in 1970. Sonesta sold the Plaza to Western International Hotels in 1975 for $25 million (equivalent to $119 million in 2019). Western International changed its name to Westin Hotels in 1981 and the hotel was renamed soon after, becoming the Westin Plaza.

Westin sold the Plaza to Donald Trump for $390 million on March 27, 1988 (equivalent to $843 million in 2019). Trump commented on his purchase in a full-page open letter in The New York Times: 
I haven't purchased a building, I have purchased a masterpiece—the Mona Lisa. For the first time in my life, I have knowingly made a deal that was not economic—for I can never justify the price I paid, no matter how successful the Plaza becomes.
 Trump installed his wife, Ivana Trump, as the hotel's president. After $50 million in renovations, the hotel was earning a healthy operating income, but not enough to make the payments on its heavy debt load. Trump made plans to pay off the hotel's debt by selling off many of its units as condominiums. A deal was instead reached for the Plaza's creditors, a group of banks led by Citibank, to take a 49% stake in the hotel in exchange for forgiveness of $250 million in debt and an interest rate reduction. The agreement was submitted as a prepackaged bankruptcy in November 1992.
In 1995, CDL Hotels International and Saudi prince Al-Waleed bin Talal purchased a controlling stake in the Plaza in a deal that valued it at $325 million (equivalent to $545 million in 2019).
Plaza Hotel