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Robert's first marriage—to Ruth S. (née Lamar) Rumsey (born 1902) in May 1929 in Montreal, Quebec—ended in a divorce about 1931. Previous to her marriage to Robert, Ruth Lamar had been married to John Williams "Jack" Rumsey (1877–1960), who was owner of the Embassy Club (a nightclub in New York City) and president of the American Play Company (an old established literary agency located at 532 Fifth Avenue in Manhattan).

After his death in 1969, the Robert Lehman Foundation donated close to 3,000 works of art to the Metropolitan Museum of Art. Housed in the Robert Lehman Wing, which opened to the public in 1975, the museum has called it "one of the most extraordinary private art collections ever assembled in the United States." To this day, his Foundation remains active, operating the Robert Lehman Art Lecture Fund and sponsoring exhibitions in museums, both around the U.S. and worldwide. Other philanthropic activities include support for PBS television programming. The Robert Lehman Art Center at Brooks School in North Andover, Massachusetts, is named in his honor.

He died August 9, 1969 and is interred in Woodlawn Cemetery in the Bronx, New York City.

Robert's third marriage—to Lee "Elena" (Anz) Lynn (1919–2006)—occurred on July 10, 1952 in New York.

Robert's second marriage, which occurred on June 25, 1934 in Washington, D.C., was to Ruth "Kitty" (Leavitt) Meeker (1904–1984), daughter of William Homer Leavitt and Ruth Bryan Owen, and granddaughter of United States Secretary of State, William Jennings Bryan. They had one son, cinematographer and director, Robert "Robin" Owen Lehman Jr. Meeker had three daughters from her first marriage to William Painter Meeker (1902–1983) whom she divorced in 1933: Ruth Meeker, Helen Meeker, and Kathrine Meeker. Robert and Ruth Meeker's marriage also ended in divorce in 1951.

Robert Lehman guided his company through the perils of the stock-market crash of 1929 and the ensuing Great Depression of the 1930s. Post-war, he grew the company substantially, expanding to Paris, France to meet the financial needs of his clients with international operations. In the process, he made himself one of the wealthiest people in the United States.

While sound financial principles were essential, Robert Lehman was often quoted as saying that he "bet on people." One of those people he believed in was Juan Trippe who would build Pan American World Airways into an industry powerhouse. Robert Lehman understood that to maximize Lehman Brothers' growth he needed additional investor capital. While still maintaining voting control, he was the first to invite non-family members to become partners. He understood too that the right partners could expand the company's opportunities through interlocking directorships. As such, he sold an interest in Lehman Brothers to John D. Hertz who had sold his Yellow Cab Company and The Hertz Corporation for a fortune and who sat on the board of directors of General Motors. Under Robert Lehman, the bank concentrated on rapidly developing consumer industries with financing deals arranged in retailing, airlines, and the entertainment business notably with the Keith-Albee-Orpheum theatre group 1928 deal that sold the majority of its stock to Joseph P. Kennedy which led to the creation of RKO motion picture studios. And, when Lehman put together start-up financing for Paramount Pictures, John D. Hertz would be their connection on Paramount's board.

For six decades he built upon an collection art collection begun by his father in 1911 and devoted a great deal of time and energy as a long-time member of the Board of Trustees of the Metropolitan Museum of Art, and finally becoming the first chairman of the board at the Metropolitan in the 1960s. The importance of his collection became such that in 1957, nearly three hundred works were used for a solo exhibition at the Louvre Museum's Musée de l'Orangerie in the Tuileries Gardens in Paris. At that time, his was the only private American collection to be given that honor. In 1968 he received an honorary Doctor of Humane Letters from Yale University for having "enhanced the civic life, the culture, and the artistic development of our civilization."

He graduated from Hotchkiss School in 1908 and was a 1913 graduate of Yale University and member of Delta Kappa Epsilon fraternity (Phi chapter). When his father retired in 1925, "Bobbie" Lehman assumed the leadership role of the family-owned business. He took over the bank during a time when Lehman Brothers, like its competitors Goldman Sachs and Morgan Stanley, was essentially a one-office firm.

Robert Owen Lehman, Sr. (September 29, 1891 – August 9, 1969) was an American banker, longtime head of the Lehman Brothers investment bank, and a race-horse owner, art collector, and philanthropist.

Lehman was born to a Jewish family in New York City. He was the son of Philip Lehman (1861–1947) and grandson of Emanuel Lehman, a cofounder of Lehman Brothers investment bank, and Carrie Lauer (1865–1937).