How a Donkey Challenged Me to Accept His True Nature & Rediscover My Own

By Margaret Winslow

New World Library; Non-fiction; ISBN 9781608685905; 277 pages; Paperback, E-Book

Reviewed by Margaret Evans

When Margaret Winslow decided to buy a donkey, she had no idea that her 700 lb white donkey, Caleb, was going to come with some expectations of his own.  

An overworked field geologist and professor emeritus of Earth Sciences at the City College of New York, Winslow decided to meet her midlife agenda not with a world-trip sabbatical, but by answering a for-sale ad for a “large white saddle donkey” and fulfilling her childhood wish for a Mexican burro. She had no idea that owning Caleb would not only upend her life, but her understanding of herself.

Her book Smart Ass: How a Donkey Challenged Me to Accept His True Nature and Rediscover My Own, is an absolutely delightful – and at the same time thoughtful – book of the starts, stops, tears, training highs and very lows, hilarity, and insights of Winslow’s life on the trail – or in the ring with cones and rails – riding her great white donkey. Every time, Caleb had his own idea about the session of the day while her oceanographer husband Joe Stennett, friends, and trainers helped her along the way. Sort of.

“Right before our next lesson, Caleb unexpectedly dragged me straight from his stall to the big ring. I mounted in the usual haphazard manner and he threaded his way between the cones, both up the line and back, veering aside at one point but knocking over only one. Too bad [friend] Laura wasn’t there to see it. When she joined us, Caleb set off again through the obstacle course, snatching the traffic cones and dropping them here and there until he had arranged them to his satisfaction, as if auditioning for a job with the highway department.”

Out on trails, it was no different. Caleb would take issue at manholes, believing each one to be the entrance to the underworld. And it was no help either when, trail riding Caleb along a quiet road with her husband riding his bike in front, they saw a dozen adults outside a largely abandoned psychiatric centre. While Caleb stiffened, pranced, and snorted past yet another manhole cover, Winslow tried to ease him, hoping fervently the group wouldn’t notice her prancing white donkey.

“Out of the corner of my eye, I saw someone sprinting toward us clad in pyjamas, a terry-cloth robe, and slippers,” she writes. “There were inpatients here after all. The man stumbled and slowed, tripped up by the belt of his trailing robe, but continued to approach. Half a block away he raised his arms in a gesture of…what? Supplication? Horror?

“‘Caleb, let’s go!’ I kicked harder and hauled hard on the right rein. ‘Move on! Now!’ What would the patient do when he reached us? More important, might Caleb, already panicked by the gurgling monster under the iron lid, trample the man?”

Caleb’s antics and Winslow’s trials would take them from the ring to the side roads, to competitions, and to churches whose ministers begged to borrow Caleb for Christmas nativity shows. But pressures and frustration piled on Winslow as her crisis at work led to a crisis in winning over Caleb. It would take both to new levels as she saw in herself what Caleb was trying to show her. For all the misunderstandings, false starts, frustrations, avoidances, and ringside antics, Caleb gave Winslow what she needed more than anything – his forgiveness of all things misunderstood. Including herself. 

Smart Ass is a delightful book on so many levels. Winslow has some seriously troublesome moments with Caleb, ones that riders with any kind of challenge might face. But they lead the story of Caleb and Winslow on such a unique, enriching journey that is both satisfying and poignant.

This book is a wonderful gift for anyone. And for yourself.