Lucretia Osborn McKleroy
“The Most Interesting Woman in the World… that you never heard of”
Photos courtesy of the William H. McKleroy Family

Lucretia Perry Osborn McKleroy was a poet, playwright, model, novelist, docent\staff at the MET, SF’s Legion of Honor and de Young, equestrian, skilled skier, Girl Scout leader, Red Cross nurse. All while as a socialite of New York and San Francisco. Her work was published in The New Yorker, San Francisco Magazine and produced on stage.


Lucretia lived in Glen Cove Long Island, Garrison and Manhattan, New York, Florence, Italy, Carmel, CA, San Francisco, and Alpine Meadows (Lake Tahoe). Lucretia (Lu) was the daughter of prominent New York lawyer Lt. Col. Alexander Perry Osborn, of the famed William Henry Fairfield family, known for paleontology discoveries such as the velociraptor and T Rex, as well as their friendships with notables Teddy Rosevelt, John Muir, and Hudson River School artists as Frederic Church and Albert Bierstadt. Her linage included historic Naval heroes Oliver Hazard Perry and his brother Commodore Matthew Perry.
Born in 1916, a rare event of the time shook her life near her fifteenth birthday. Lucretia’s mother, Anne (ne Steele), abandoned her wealthy husband, Lucretia, twin daughters and much younger son. Anne would later be humorously called “The Bolter” from the oddly similar incident in the 1930s of another known beautiful debutant socialite leaving a wealthy husband. The bio The Bolter on Idina Sackville, was written by the daughter, Frances Osborne (unrelated to the Osborns), and was the basis for the film White Mischief. As the oldest child, Lucretia took on many of the burdens of sibling management from the working father.
Lucretia’s love of equestrian activities helped her overcome the bolting of her mother. This culminated with her adoption of the horse, “Cedarbrook.” The family was quite surprised to discover whenever the horse heard music he would rear up and dance on hind legs. They had not known that Cedarbrook had previously performed in a circus! Lucretia loved the magical musical Cedarbrook and soon put on her own circus shows for friends. Lucretia ‘s adventures of riding atop dancing Cedarbrook became talk of the town. The horse became the titular subject of her novelized biography published at age sixteen. (Photos coming soon.)
Little Lu summered at the family estate’s “Wizard of Oz witch’s castle” (according to some the inspiration for the movie’s castle). “Castle Rock” is the estate of former Illinois Central Railroad president William H. Osborn in Garrison, NY. Castle Rock, is one of the most recognizable man-made landmarks of the Hudson River Highlands. Donated to the state by the family, the property was recently purchased by Mr. Whipple (“Please don’t squeeze the Charmin”). Really.


Lucretia was quite the belle of the ball with her beauty and social-column mentions seducing West Point cadets to recklessly swim across the mile-wide Hudson River to Castle Rock to woo “the princess of the castle.” On ocean voyages she was always seated at the Captain’s table.
This most eligible bachelorette met her match in William Henry McKleroy Jr. on a upstate NY ski lift. The impressive six three 230 pound McKleroy was a charming southerner. From a Aniston, Alabama banking family, she would soon be engaged and their marriage linked two established American families—Yankee and Southerner. William would become an Army Lt. Col. himself (like her father) during WWII.


Relocated to Monterey with her husband’s appointment to Fort Ord, the young couple would post-war move to San Francisco. William McKleroy used to banking savvy to purchase real estate for the baby boom. Despite his size, William was an agile and graceful skier and ice skater.
In the sixties become key supporters in the development of Alpine Meadows ski resort (now with Squaw Valley known as Palisades). Their five children were avid skiers and often local NASTAR race winners. Lucretia and her husband were well-known for their Christmas parties at their long-time Pacific Heights pink home.

Tales from Two Valleys” by Eddy Star Ancinas.



Tragedy would strike twice with sudden deaths of first her eldest son on Christmas Day rushing up treacherous old Highway 80 with his new Christmas present skis and then her husband from a heart attack while playing tennis. Lucretia became the matriarch of the well-known McKleroy family, raising the remaining four siblings as a single mother. She maintained her family’s prominent standing within New York and California high society.
She passed on 12 March 1994 at her home at the age of 77 with a memorial held at Grace Cathedral. She is at rest alongside her beloved husband and son at Trail’s End cemetery in Tahoe City, CA.

Read Lucretia Osborn McKleroy poetry sampler here.
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