Sidelines October 2026

This Issue! John French—Treasure to the Sport; Cyndi Jackson—Dressage to the Max; Grace Stenbeck-Werner—One Ride at a Time; And Much More!

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SIDELINESMAGAZINE | October 2026

itting jump seat in the cockpit of

a FedEx cargo plane, eyes closed

but ears intently listening for any

sound indicating one of the three horses in

the cargo area may be discontent, Natasha

Klingenstein, business operations manager

for the international transport company

Horseflight, briefly wondered what she had

signed up for. Her first job as an in-flight

groom was a grueling “milk run,” where she

was getting four flights’ worth of experience

over one continuous 26-hour journey.

The aircraft crisscrossed the country

from Florida to Alaska, making stops in

NATASHA

KLINGENSTEIN

Flying High With Horses

By Diana Bezdedeanu • Portraits by Kacy Brown

Memphis, Los Angeles and Seattle while

temperatures plunged from 90 to 38 degrees.

“Ultimately, that experience confirmed I was

exactly where I was meant to be,” Natasha

recalled. “I felt that I was directly impacting

these horses’ lives by making what could be a

stressful experience positive and comfortable.”

LEARNING TO FLY

Although Natasha’s career now centers

around horses flying 30,000 feet in the air,

that’s not where her love of equines began.

Growing up in Torrance, California, her initial

exposure to horses was at a nonprofit self-care

co-op barn right in the middle of the city. This

no-frills stable taught Natasha responsibility

and that caring for horses isn’t glamorous; it’s

showing up every day and giving them your all,

even when no one is watching. Reminiscing,

Natasha laughed, “When I was little, I thought

I was going to be a cowgirl because the horse I

was riding at the time was ex-rodeo.”

That dream shifted during a family vacation

when she was 10 years old. While trail riding at

a dude ranch, her horse encountered a log lying

across the path. Rather than simply stepping

over it like every other horse had done, her

horse launched over the obstacle. “That flying

Natasha Klingenstein in

Ocala, Florida.