in 1864 and was a member of Skull and Bones and president of Brothers in Unity during his senior year.

[1] He graduated from Columbia Law School as the valedictorian of the class of 1867 and was admitted to the bar in that year.

He became a corporate lawyer in New York City, and in 1871 helped found the law firm of Shearman & Sterling, which represented Jay Gould, Henry Ford, the Rockefeller family, and Standard Oil.

In 2003, historian Jonathan Ned Katz uncovered evidence that Sterling lived for nearly fifty years in a same-sex intimate partnership with cotton broker James O.

[6][7][8][9] Sterling died July 5, 1918, while staying at the fishing lodge of Lord Mount Stephen in Grand-Métis, Quebec;[4] he is entombed at Woodlawn Cemetery.