Jocelyn Mary McKeever

Jocelyn Mary McKeever, 65, horse trainer and antiques dealer, died early in the morning of May 17, 2026 after an on and off struggle with breast cancer. 

Jocelyn was born on Aug. 14, 1960, the third daughter among the nine siblings of Chris and Kay McKeever of Water Mill, N.Y.  She attended Sacred Heart Grade School and Southampton High and after a stint at the University of Georgia, she transferred to SUNY Morrisville, in upstate New York, and earned her degree in Horse Husbandry.  

Jocelyn moved to Maryland and worked as a groom, then as an assistant trainer. As she became more familiar with training for the track, choosing races, keeping the horses superfit and getting to know the owners and other track personnel, she went off on her own, training not just for specific owners, but for herself as well.   

Being a horse trainer, especially a woman horse trainer back then was rather difficult. She persevered and had a number of good horses and wins. How thrilled she was to see Cheri Devoe become the first woman trainer to win the Kentucky Derby this year! 

During her entire career involving horses, she made 691 starts winning 97 races, with 103 seconds and 99 thirds, earning $1,184,186 shared among the owner, jockey and trainer. That’s an overall record of 43% of her entries ending up in the money, proof of her meticulous study of the form and her astute choice of not only the particular race, but also of the competition. Among her favorite winners were: Lady Cordelia, Belinda O’Britis, Slew Pet Girl and Slew O’ Quoit.

After closing the barn door, she returned to Water Mill to help care for her mother. In the Hamptons, she loved to go to yard, garage or estate sales looking for objects for resale. 

Jocelyn could find treasures, both old and new, for a few dollars that she resold through eBay, various auctions or from her booth in a local antique shop.  She loved the different, the peculiar, the eccentric, the unique, knowing that many unusual items will find a buyer. 

What she liked best was researching her finds. What a delight to clean up an object like a tarnished silver salver to discover it was from the 18th century as she had thought. One time,  Jocelyn purchased a bag of small decoys and asked a knowledgeable colleague what he thought they were worth, he hemmed and hawed and said some were a little valuable and he would give her $500 for the lot. Her antennae quivered down on Maryland’s eastern shore, she visited a decoy collector who ultimately gave her $3,000 for the lot!

Jocelyn was brilliant and kind, wise and generous, talkative, and maybe, at times, a wee bit stubborn, but happy to socialize and equally pleased with her own companionship and that of her beloved dog, Zenyatta.

Jossie will be missed by her family as well as many from all different walks of life. She was predeceased by her brother Kent last year and is survived by her seven siblings: Chris (Nona), Kilda, Clare (Danny), Robert (Trina), Daniel (Cindy), Matthew (Dawn) and Colin (Maura). She was an amusing and fun aunt to 15 nieces and nephews. 

A memorial service will be held at a later date.

Donations in her honor may be made to: Permanently Disabled Jockey Fund, PO Box 910864, Lexington, KY 40591 or the Water Mill Community Club, PO Box 182, Water Mill, NY 11976.

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