Earl Edward Tailer Smith (July 8, 1903 – February 15, 1991) was an American financier and diplomat, who served as ambassador to Cuba from 1957 to 1959 and mayor of Palm Beach 1971 to 1977.

Smith was born in Newport, Rhode Island on July 8, 1903. He was a son of Frances Bogert "Fannie" Tailer (1884–1953),^[1] and Sydney Johnston Smith (1868–1949), a cotton broker and sportsman.^[2] His parents divorced in 1909 and his mother remarried to C. Whitney Carpenter in 1916.^[3] They also divorced.^[4]

His maternal grandparents were Edward Neufville Tailer, a prominent merchant and banker,^[5] and Agnes Suffern^[6][7] (the daughter of Thomas Suffern).^[8] His aunt, Agnes Suffern Tailer Burnett, was the wife of U.S. Attorney Henry Lawrence Burnett.^[9] Another aunt, Mary Tailer Livingston, was the mother of New York Assemblyman Robert Reginald Livingston, a descendant of Chancellor Robert R. Livingston.^[10]

He was educated at the Taft School in Watertown, Connecticut followed by Yale University in New Haven, Connecticut from 1926 to 1928.

Before becoming an investment broker and a member of the New York Stock Exchange. In 1929, he was a founder of the investment brokers, Paige, Smith, and Remick, serving as senior partner until 1937 and remaining a member for more than 60 years.^[11]

In 1941, President Franklin Roosevelt appointed Smith as special assistant in the Office of Production Management (later War Production Board). He left this post to serve in the United States Army during the Second World War. He served overseas and by the end of the war reached the rank of Lieutenant colonel.

As a successful businessman, he became the finance chairman of the Florida Republican Committee.^[12]

Smith was married four times and divorced twice. His marriage was on January 7, 1926 to Consuelo Vanderbilt (1903–2011),^[16] a daughter of the former Virginia Graham Fair and William Kissam Vanderbilt II. Consuelo, the sister of Muriel Vanderbilt, was also a granddaughter of William Kissam Vanderbilt, Alva Belmont, James Graham Fair, and a niece of Harold Stirling Vanderbilt and, her namesake, Consuelo Vanderbilt (the former Duchess of Marlborough from her marriage to Charles Spencer-Churchill, 9th Duke of Marlborough).^[16] Before their 1935 divorce, they were the parents of two daughters:^[17]

• Iris Vanderbilt Smith (1927–2006),^[18] who married Herbert Pratt Van Ingen, Augustus G. Paine III, Edwin F. Russell,^[19] and Donald C. Christ.^[20]
• Virginia Consuelo Smith (b. 1930), who married William Langdon Hutton and Edwin Marston Burke.

The year after their divorce, Consuelo remarried to Henry Gassaway Davis III (the heir to a coal fortune who was recently divorced from her cousin, Grace Vanderbilt, a daughter of Grace and Cornelius Vanderbilt III).^[16] Smith remarried to Mimi Elaine Richardson (1916–1995) on December 28, 1936.^[21] Mimi, a graduate of Miss Porter's, was a daughter of Courtlandt Richardson of New York.^[21][22] They divorced in November 1939,^[23] and she married William Gamble Woodward Jr. in December 1940.^[24]

In 1947, Smith married fashion model Florence Pritchett Canning (1920–1965). Flo, as she was known, was the former wife of Richard Canning. She and Canning divorced in 1943. She met John F. Kennedy in 1944.^[25] They may have dated, and remained friends through his presidency.^[26] Pritchett was also romantically linked with actors Robert Walker^[27] and Errol Flynn.^[28] In the 1940s she worked as the fashion editor for the New York Journal-American^[29] and wrote articles for Photoplay.^[30] She appeared as a panelist on the radio and TV program Leave It to the Girls from 1945 to 1953.^[31] Before her death in 1965, they were the parents of:

• Earl Edward Tailer Smith Jr. (b. 1953)

After the death of Smith Sr.’s third wife Florence from leukemia in 1965, he married for the fourth, and last, time to the former Lesly H. Stockard at the Atlanta County Courthouse in March 1968. Lesly, a daughter of Lester Napier Stockard, was the former wife of John Barker Hickox and James Langley Van Alen (son of Margaret Van Alen Bruguiére).^[32]

Smith died at his home in Palm Beach, Florida on February 15, 1991.^[11]

• Cuba-United States relations
• History of Cuba