Cassandra Naupac
Horse Racing

Women in Racing – Cassandra Naupac

For three and a half years after the birth of her son, Cassandra Naupac held on to her racing equipment, despite barely using it. Just two months after deciding to sell her tack, she returned to riding race horses. She decided it was time to put herself first once again – and jockeying was exactly what that meant.

Born and raised in Pittsfield, Massachusetts, Cassandra did not come from a family of jockeys – no one she knew was involved in the industry for that matter. In fact, she didn’t even live near a track. Nonetheless, she grew up an avid lover of horses and dreamed of being a jockey as a young girl. Cassandra and her father spent summers on the lawn at the fair circuit in Northampton, 45 miles away from home, placing $2 bets on the horses with the best names or the prettiest faces.

At 15, she began hunter/jumper lessons, and just two years later, she found herself trekking 1,000 miles away from home to begin her jockeying career. With a move to West Virginia on a wing and prayer from a kind woman offering to teach her, Cassandra worked her way up from a hot walker to a groom and then ponying racehorses and breaking babies and finally to jockeying full time.

A Bond Forged on the Track Lasts to Today

Cassandra’s first win came on July 4, 2010 on a horse named Handsomely… who had a not so handsome race record. New to trainer Brian House’s barn at Louisiana Downs, Cassandra was optimistic that the dark bay colt was ready for a comeback. The moment the starting gates opened, Handsomely took to the track like an old pro.  With a relatively hot early pace, Handsomely and Cassandra took the lead on the backstretch. Cassandra recalls that race, and it’s stretch run, the best:

“I felt like I was in a good spot in the final turn and just hoped he would have enough to stay in front to the wire. And then I heard them. Creeping up on my outside, Patrick Valenzuela and Bee Tree. And they were rolling. I started urging Handsomely on using my whip and my hands and also my voice. And then they got even closer. I could see them in my head just going by me and thought to myself, ‘Dang, we’re going to run second’. But I wasn’t giving up without a fight. I was hollering, ‘C’mon, Handsomely, c’mon!!’. And he showed me he wasn’t ready to give up without a fight either. He dug in for more and that made me push even harder… I was as low as possible, pushing on his neck to encourage him with everything I had. When we passed the wire I looked over at [Patrick] instantly and he smiled at me.”


Cassandra and Handsomely came out on top that trip, and three years later their fate would intertwine once again.  One night after putting her son to bed, Cassandra came across a post from a horse rescue as she scanned through her Facebook feed. The face of a horse all too familiar sent Cassandra’s heart racing. The horse, “Handsomely,” was set to be auctioned off to the highest bidder – who would more than likely be the meat buyer. In one swift moment, the jockey who had ridden him to a win all those years ago was about to drive him to the most important victory of his life. Cassandra and his former trainer Brian House rallied a crowd of fans to raise funds to purchase Handsomely, and within 72 hours the two were reunited.

Cassandra and Handsomely are still together today as he lives out his days with his jockey and together they advocate for the care and versatility of retired Thoroughbreds.

A Sport and Career Providing Both Challenges and Opportunities

Since that win on Handsomely in 2010, and the many races and wins since, Cassandra has soaked up the knowledge of the jockeys around her and learned from the trips she has taken on a racehorse’s back. “I’ve met some amazing riders and trainers. The most important thing is being willing to listen and accept advice and then apply it. I still learn something every time I ride.”

There is an added complexity to being a female jockey, Cassandra notes. Certain trainers and owners simply don’t give women in the sport a fair shake. It’s something that is echoed through more than just sports as women fight for a level playing field to their male counterparts. In horse racing, however, with the need for physical strength and fitness so integral, it’s easy for women to simply be overlooked. When Cassandra became a mother she gained weight – the ultimate crux for all jockeys but perfectly normal for a woman carrying a child. After her son’s birth Cassandra didn’t think returning to the sport as a rider was in her cards. With a young son and a new husband fresh in his own jockeying career, Cassandra put her dreams of riding on hold. Committed to raising a child it was two years before she got back up on a horse and three and a half years later, after only sporadic sessions on horseback, when she sold her racing tack.

And then something changed.

At some point there began a small tug on Cassandra’s heart. There were early morning frosts that could have been warmed by the hot breath of a horse after a workout. There were finish lines crossed, win photos snapped, and opportunities grabbed by other jockeys. There were dreams that kept creeping into daylight, desperate to no longer be kept to night time fantasies. So, just two months after selling all her equipment, Cassandra decided to return to racing. Finally ready to put her own happiness first – from the back of a Thoroughbred.

Today, returning to the sport as a woman, mother and jockey, Cassandra is taking a different approach. Everything is with a new purpose. Physically, she is healthier and stronger than ever before. As a business woman, she navigates her relationships with trainers and owners with a patience and wisdom she lacked before. She studies her races, she understands the horses she rides on a different level, and she values every opportunity she gets to put her feet in the irons.

There is more at stake these days for Cassandra, too. Riding race horses is no longer about dreams of finding fame and success like it once was. There’s a new dream now – one of providing her family with stability; a chance to buy a home and send her son to college. A chance to make a difference in the lives of racehorses in retirement, as she has done for Handsomely. A chance that, some day, young girls will look to her for inspiration as proof that they too can shatter the glass ceiling. There’s something deeper too. There’s a desire to leave a legacy for her son.

“I want him to know that nothing is unachievable. If you really, truly want something, all you have to do is keep your head up and work for it. Nothing is ever going to be handed to you or come easy.”

Sometimes it takes stepping away from what we love the most to gain a new perspective and appreciation for it. When you add seeing it through the lens of a mother that becomes even more powerful. Cassandra had thrown in the towel, the odds definitely not in her favor as a mother… and a woman in a male dominated sport. Instead of giving up, she has battled back. She is back in the race and there’s only one destination in sight from here: the finish line.

With a new determination, and a deep passion for not just winning races but for creating a future – a legacy to outlast her moments in the winners circle – Cassandra Naupac is destined to make her mark.


Article written by Eliya Finkelstein

Chief Storytelling Officer

This Post Has One Comment

  1. Laura Reply

    You and I would have much to talk about comparing careers I suspect. Sure enjoyed the read Cassandra. And Kudos to you, for your efforts in saving Handsomely!! Well done, you do Rock! That’d been the best thing to read, as I love those that have the heart to save any horse from the meat man, or a slaughterhouse!! You and that horse had gone full circle, what a thing it is for you to give back this way! May God Bless you and your family. Good Luck at the Races!!!

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