Home Business and Labor John William Sterling, a Well-Respected Man With a Secret

John William Sterling, a Well-Respected Man With a Secret

Wealthy, successful, distinguished ... and gay

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John William Sterling was a corporate lawyer during the Gilded Age, a conservative, upper-class businessman, the kind of man the Kinks describe as “a well-respected man about town.”


John William Sterling

In 1911, his name and resume appeared in Distinguished successful Americans of our day. From it we learn he graduated with honors from Yale College and Columbia Law School. He advised railroad barons in building and dismantling railroads, and he served on the boards of nine large banks and gas companies. Appropriately for a man of his stature, he devoted his time to philanthropy—prestigious charities, the kind people noticed.  Eminently clubbable, he belonged to the exclusive Metropolitan, Union and American Yacht clubs.

Like the Kinks’ well-respected man, John William Sterling lived in a world built around punctuality. A Wall Street Journal correspondent described him as, “almost taciturn, and excessively devoted to his profession. He sat before his desk every morning, not later than eight o’clock, and was usually the last one in the office to close the desk and go home.”

That same correspondent also noted he had an unusual relationship that was ‘often spoken of and commented upon.’ That relationship was with a cotton broker named James O. Bloss.

John William Sterling

He was born in Stratford, Conn., on May 12, 1844. His father, also John William Sterling, was captain of the Splendid, one of the largest clipper ships during the China Trade. His mother, Catherine Plant, belonged to a prominent Stratford family; her father, David, served as a U.S. congressman and as the state’s lieutenant governor. His parents both had ancestors who arrived on the Mayflower.


Sterling Homestead

He studied at Stratford Academy, where he probably knew another young man who would lead his entire life as a bachelor, James Buchanan Mitchell. Graduating as class valedictorian, he entered Yale as the Civil War broke out.

Jonathan Ned Katz, a historian of human sexuality, notes in an essay that Sterling slept with Mitchell at Yale. His journal in September-October 1862 records: “I slept with Jim Mitchell last night an.” Katz suggests they had an ongoing relationship, as Sterling and Mitchell both chose to attend Columbia Law School.


Sterling and classmate at Yale.

His sleeping with Jim Mitchell may not have aroused much comment, wrote Katz, or at least it didn’t arouse much suspicion about what went on.

At Yale, Sterling belonged to Skull and Bones. He graduated with honors from Yale in 1864 and then from Columbia Law School in 1867 as class valedictorian.

Soon after his admission to the bar that year, he met a young cotton broker about his own age, James O. Bloss. Bloss also came from an old New England family, though he grew up in Rochester, N.Y.

Three lines of poetry clipped from the New York Times and pasted into the back of his Commonplace Book suggest Sterling’s feelings toward the man he called “Blossy.”

Once more I give me body and soul to thee,
Who hast my soul for ever: cliff and sand
Recede, and heart to heart once more are we.

Algernon Charles Swinburne wrote those lines in his poem “In Guernsey / To Theodore Watts.”

In 1872 John William Sterling and James O. Bloss went house-hunting, and they settled on 21 West 25th St. They would live together for nearly 50 years.


John William Sterling rocketed to the top of the then-burgeoning corporate world. He went to work as a clerk in a New York law firm and made partner in 1870. Three years later he had his name on the door as a partner in Shearman & Sterling. He advised another close friend, James Stillman, chairman of the board of National City Bank, then the nation’s largest. (Stillman’s great-grandson, Whit Stillman, is an Academy Award-nominated film director.)

Sterling also advised William Rockefeller, co-founder of Standard Oil and H.H. Rogers, whose firm merged with Standard Oil, as well as railroad tycoons Jay Gould and Jim Fisk.

He once said the ideal client is ‘a very wealthy man in very great trouble.’ His clients paid him handsomely for his advice, and he made a fortune.


The Sterling mansion, now a community center

In 1886, Sterling built a stately mansion, Sterling House, in Stratford, presumably a weekend house he shared with his sisters. Today the National Register of Historic Places lists the Sterling mansion, now the Sterling House Community Center.

By 1890 he and Blossy moved uptown to 221 East 47th St., where they had four servants. Eventually they moved to 912 Fifth Ave., overlooking Central Park.


Sterling clearly valued his reputation as a man of means and prominence in society. And so as Katz points out, ‘his contravention of society’s marital standard, and, perhaps, its sexual proprieties, would have been a profound source of conflict and anxiety.’

His mother was said to be happy her son didn’t inherit his father’s love of the sea. Actually, he had more than a touch of hydrophobia. He had a ‘deep-rooted antipathy to the ocean,’ wrote John Anson Garver in a biographical sketch of Sterling. He didn’t even like to take ferries, and never traveled abroad.

Anson Phelps Stokes, secretary to Yale after 1899, recalled that Sterling wouldn’t go to bed until the housekeeper poked the closet with a stick and looked under the bed to make sure there were no burglars. He had iron bars on his bedroom window and an iron door with an electric lock he controlled with a button by his bedside. Bloss slept in the room with him and his valet in an adjoining bedroom.

In Harriman vs. Hill, author Larry Haeg describes Sterling as a chain-smoking, fast walker with a fear of public speaking and a penchant for scheduling meetings at odd minutes, like 3:17 p.m. He ate dinner in the same chair at the same table six nights a week at the Union Club.

He also locked his office at work and always paid for his investments in cash. That made him a very wealthy man.

A Strange Postscript

John William Sterling died suddenly in Canada on July 5, 1918. He left $18 million to Yale and the rest to Blossy, who he named as executor of his estate.

That caused a bit of trouble. Bloss died five months later, on Dec. 15, 1918, without having completely executed the will.

Further, Sterling had died before he could execute the will of another wealthy man, his friend James Stillman, who died March 15, 1918. And Stillman had been named executor of the estate of James Gordon Bennett, who died May 14, 1918.

The first three men who died left $75 million.

Eventually Yale got its money, the largest bequest to a university up to that time.

Sterling’s gift was used to build Yale’s Law School, the Divinity School quadrangle, a School of Medicine, the Hall of Graduate Studies and the Sterling Memorial Library. He also endowed the Sterling professorships, who have included such notables as William O. Douglas, Wilbur Cross, Harold Bloom, Edmund Morgan and Paul de Man.

With thanks to Jonathan Ned Katz, “An Understanding…Held Them Together

NRHP: Sterling Homestead By Doug Kerr – https://www.flickr.com/photos/dougtone/6439034575/, CC BY-SA 2.0, https://commons.wikimedia.org/w/index.php?curid=44722867; Sterling House Community Center By Jerry Dougherty – http://public.fotki.com/GCDOUGHERTY/all-towns-and-cities/stratford-ct/stratfordsterlinghouse.html, CC BY 2.5, https://commons.wikimedia.org/w/index.php?curid=29522854. This story was updated in 2023.


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