My Summer Rental with Penny Chenery

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Four boys rented a top floor apartment on Circular Street in Saratoga Springs in the summer of 1994. Three future champion jockeys and an assistant trainer of the stars reserved the top floor in a white column mansion. You know the ones, porches, flowers, a mix of Victorian/Roman beauty and excess. Up a fire escape, along a set of stairs in the back, through a kitchen and finally up another steep set of hidden stairs, we were in the attic, at home, walking distance to the Parting Glass, cheap rent. It was sweet.

We got up early, banging down those stairs, through the kitchen, hung-over (or still flying) and were on our first set by 5:30. Blengs, Sciacca, Hushion, Hertler, Attfield were our bosses. Gallop six a day, breakfast and back up those steps, through the kitchen and we were home, late morning for a nap. Back down and through the kitchen for the races, back up after the races, back down for a night out and back up in the dark hours of another Saratoga night. Four 24-year-olds relishing a conveyor belt of freedom.

Then the conveyor belt hit a bump. 

After a hard day of work, I staggered up those steps, around the corner and through the kitchen when the sweetest voice I ever heard stopped me in my tracks. Dirty, sweaty, mud-covered after galloping all morning, I stood face to face with a woman in her bathrobe, making tea and toasting toast.

“Good morning,” she said.

“Uh, um, uh, good morning,” I said, stammering like a scolded dog.

I smiled the best I could as I looked down at the dirt I had tracked through the kitchen. I nodded and walked up the steps.

“Who’s the old lady?” asked Chip Miller, who had already kitchen-traipsed and was lying on the couch with a cold piece of pizza and an oil can of Foster’s.

“Who’s the old lady? Who’s the old lady?” I said. “That’s Penny Chenery. The Penny Chenery.”

“Yeah…” Chip said, incredulously.

Yeah, we were somehow sharing a house in a lease-finagling, boon-doggling, only-in-Saratoga arrangement. Our landlord, or at least who we thought was our landlord, lived in the basement and Penny Chenery – Secretariat’s mother, the first lady of Thoroughbred racing, the greatest of the greats – was living on the middle floor. All we had to do was dash through her kitchen six times a day without being seen.

Of course, Mrs. Chenery saw us most days, she smiled, we smiled.

Three weeks into the meet, I tiptoed through her kitchen the best I could and saw an envelope on the counter. In long, flowing, cursive writing, it said, “Boys” on the envelope. I opened the envelope and read a note.


I’ve enjoyed seeing you this summer. I’m going home before the Travers. I thought you might enjoy these.

All the best.

– Penny Chenery

Inside the envelope, Chenery placed five tickets to her clubhouse box for the week, including Travers Day. Front row and center, we put on our navy blazers and Brooks Brothers’ ties and went racing every day, culminating with a chairs-on-the-floor, leaning-over-the-rail moment of brilliance as our friend Mike Smith implored Holy Bull to win the Travers. We had never felt bigger. 

• Originally published in the Irish Field.