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James' employment epitomized the change in the upper Westchester economy over the 80 years since the house was built—the grandson of farmers, he was commuting from their land to a regular job as a commercial artist at the Manhattan offices of the Metropolitan Life Insurance Company.
His father was a past president of the Metropolitan Life Insurance Company and his mother was a hymn writer, credited with over 500 hymns, most notably "Blessed Assurance" with Fanny Crosby.
The concert netted US$13,275, with one part transferred to the Paris branch of the National City Bank of New York in order to provide immediate relief from his financial problems, and an annuity purchased at the Metropolitan Life Insurance Company, whereby he would receive US$1,250 annually for the rest of his life.
N.C. Wyeth's Pilgrims (1991) (illustrated by murals begun by Wyeth for the Metropolitan Life Insurance Company)
The square is dominated by the former headquarters (until 2005) of Metropolitan Life Insurance Company and the headquarters of New York Life Insurance Company, located on the site of the original Madison Square Garden.
Throughout his career, he has arranged transactions for some of the US's most prominent corporate clients including J.P. Morgan Chase & Co., Sidley Austin Brown & Wood LLP, Fried, Frank, Harris, Shriver & Jacobson LLP, Amerada Hess Corp., Sanford C. Bernstein & Co., Swiss Reinsurance, MetLife, Cerberus Capital Management and Akin, Gump, Strauss, Hauer & Feld LLP.
From 1904 he was president of the International Banking Corporation (subsequently merged into the company now known as Citibank) and was a director of the American Light and Traction Company, Metropolitan Life Insurance Company, National Bank of Commerce in New York, Toledo, St. Louis and Western Railroad Company, Wabash Railroad Company and the Western Union Telegraph Company.