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Simply Ali

Ali with her dog Enzo.


"I've taken a number of business calls while hanging on Tigerlee like this,” Ali DeGray said, her right arm flung over the withers of the reigning Amateur Five-Gaited World’s Champion of Champions Memories Of Cabo, as he rested in his stall at the American Royal.

The chestnut gelding and Ali had a nearly undefeated first season together, winning in nine of their ten show ring appearances, from River Ridge to Louisville, and earning another two blues that very week in Kansas City. He was, by all accounts, one of the most celebrated show horses of the year, but to Ali he is only “Sammy,” just as the multi-titled World’s Champion CH Tigerlee is simply “Tiger.”

Fanfare doesn’t mean much to Ali. At 26 years old, she is keenly aware that she comes from a privileged family, one that is able to provide her with horses like Sammy and Tiger, and give her the opportunity to show them at the highest levels, but there is much more to her than her background and show ring record would indicate. She is a woman of substance; fiercely in love with her horses and other animals, hard working, approachable, filled with unlimited appreciation for all her life’s blessings and determined to utilize those blessings to enrich the lives of others.

Ali and her mother Helen share many similarities including a love of horses and animal rescue and a kindness that extends to everyone they meet.

Ali’s mother, Helen Rich, is a granddaughter of chewing-gum magnate William Wrigley, Jr., but she raised Ali with a very balanced view of the world.

“My mother is obviously a very wealthy woman, but I don't think I even knew that until I was a teenager because she was always wearing overalls and finding cats in bushes,” Ali said.

And when Helen wasn’t rescuing kittens or other animals she was playing the role of “mom” to everyone around her – whether Ali’s friends or total strangers – or lending horses to people who were in need of them.

“If a horse has such a good personality I'll often say it needs to be with a kid, and she'll literally just give them to kids and say, “When you're done give them back,’” Ali said.

Kindness is typical of Helen; when Ali’s friend and fellow horse show exhibitor Justin Cowley was struggling with kidney disease a few years ago, Helen swooped in to help with medical expenses and logistics, flying him to different hospitals for surgery and flying his friends, including Ali, up to visit him. And when he didn’t have a horse to show in 2011, she let him show her road horse all year, something he considers one of the highlights of his career.

Ali visiting her friend Justin Cowley in the hospital. She and her mother Helen have helped Justin through his illness in various ways.

“Helen has helped me in so many ways it's hard to really list all the things she's done for me,” Justin said. “Every aspect of my life Ali and Helen are a part of or have been a part of – my horses, my health, my business – and I consider them family.”

Her mother’s generosity has not gone unnoticed by Ali, who patterns her life after these same values.

“I guess she just taught me that not only isn’t anybody different than anybody else, but if you are lucky enough to be blessed with all of this stuff you share it,” Ali said. “And I don't like mean people. There is really never any excuse to be unkind.”

According to Justin, Ali is one of the kindest and least pretentious people he knows.

“I would say Ali does a really good job of being ‘normal’ considering her circumstances,” he said. “She hangs around a lot of grounded people, and she grounds me and I think I ground her.”

Because of this, Ali prefers to be known for more than her family’s monetary status.

“It's irrelevant and I want it to continue to be irrelevant,” she said.

Instead, she likes to focus on things she finds more important, and near the top of that very long list are the horses.

Ali is a fifth-generation horsewoman, hailing from a family background in Arabians and National Show Horses. During her childhood, her aunt, Misdee Wrigley-Miller, had a farm in Ocala, Florida, and Helen and Ali were constant faces at the barn, even keeping a number of their own horses there.

“I didn't have a choice, which I love,” Ali said. “If they could’ve duct taped me onto a saddle they would’ve done that.”

Alis first Saddlebred was a large chestnut gelding named Somersby.Ali goofs around with her hunter horse Jolly Mon Sing.

Ali, who had grown up in the western discipline, was a very shy child, but she remembers speaking up the first time she saw a horse performing a posting trot.

“I said, ‘I want to do that,’” Ali said. “They told me, ‘That’s a National Show Horse. They’re really fancy and half Saddlebred.’”

Ali was fascinated by these fancy horses, but she was also scared to get on them.

“At the time I was terrified of riding,” Ali said. “I had so many bad falls and trail rides gone awry.”

But the horses were so alluring that she pushed aside her fear and did it anyway. Tom and Nancy Scott trained for Misdee at the time, and it was Misdee and Nancy who gave Ali her first saddle seat lessons on a sweet Arabian mare named Kaabor’s Doll – a gift from Ali’s grandmother.

“I'm so incredibly proud of her and where she came from, because she started out not being as confident of a rider as she is now,” Misdee said. “She'd be so afraid but just keep on with that Ali spirit. I know today Mom is up in Heaven smiling down going, ‘Yes! She got the horse gene.’”

When Ali was seven the Scotts and Misdee went separate ways, which left Misdee searching for a place to send her horses. Misdee knew that trainer Ruth Gimpel was located in nearby Tampa and had some National Show Horses, so she called and asked if Ruth could take her in. Ruth did, and when Misdee moved, Helen and Ali went with her, paving the way for Ali’s introduction to Saddlebreds.

“Ruth really got me out of my shell and was patient with me and taught me,” Ali said. “We had the rainbow reins and the posting strap.”

In 1998 she got her first Hackney pony, a bay gelding named Among The Stars, or “Hoppy.”

“We got a Hackney pony probably because I was so scared of everything else,” Ali said.

Ali and her partner Memories of Cabo were the 2015 Amateur Five-Gaited World's Champion Of Champions.


Ali was so small that when she showed Hoppy they would load a fifty-pound bag of sand into the cart with her so the pony could tell she was back there. The sand bag also served as a footrest, since Ali’s feet weren’t even close to touching the bottom of the basket. When Ruth decided that Ali and her new pony should go to Louisville, Ali took special note of her mother’s response.

“My mom said ‘I only want her to go if she's not going to win,’” Ali said. “Ruth asked why and she said, ‘Because I don't want her to think that's how things happen. You don't just go and win. If I wanted blue ribbons I would’ve bought a blue ribbon factory.’”

Ali and Hoppy didn’t win. They took a sixth place in their qualifier and left without a ribbon in the championship, but Ali was thrilled and the experience left her eager for the next step. That step would come two years later in the form of her first Saddlebred, the renowned chestnut gelding Somersby, or “Gumby.”

“He'd had a lot of really talented riders, and then me, who couldn't tell her right lead from her left,” Ali said. “I remember he had the cleanest bottom half because I would clean him really well, but he was a huge horse so I couldn’t reach the top half.”

But, though his size was intimidating, Gumby was an excellent teacher, carrying Ali safely through many lessons and large pleasure classes despite her fear.

“Somersby taught me how to connect with a horse and trust,” Ali said.

He was also the first horse she rode onto the Green Shavings at Louisville, and, while they never won there, he prepared her well for everything that was to come. She won her first World’s Championship with the great CH Free Willy in the Junior Exhibitor Road Pony 13 & Under division in 2002, and that was just the start.

There would be many more Louisville victory passes to follow, with horses and ponies such as Autumnwood’s Rumor Has It, CH Tigerlee, Seize The Moment, I’m Good To Go, Kalarama’s High Roller, Imagine That, Roar Of Thunder, Heartland, Elegant Touch, Harlem’s Worldly Lady, Most Definitely Diamonds, Starlight Voyager and Heartland High Tech. This year she added Memories Of Cabo, Twin Willow’s McDreamy and Craycroft Matador to that list.

The reigning Hackney Pony World's Grand Champions, Ali drove Craycroft Matador to win the Open Hackney Pony qualifier and Hackney Pony National Championship at this year's American Royal under the Majestic Oaks banner.


Though she has now been showing there for fifteen years, Ali still views competing at Louisville as an immense privilege, and is as excited as a child, every single time

“I think if you lose that, you lose sight of everything,” she said. “You may as well do something else.”

But, for all the excitement and meaning Ali attaches to showing, especially at Louisville, there is never any pressure; she and her mother both agree that their first priority is the happiness and health of their horses.

Ali kisses her horse Northern Asset. One of her favorite activities is spending time with her horses in their stalls.“She would never push a horse for a career,” Ali said of her mother. “And if I come out of the ring and I missed a canter she'll say ‘canter much?’ She never pressures me or makes me feel badly. She’ll make fun of me, but it’s good-natured.”

And she is always there with encouragement – something that Ali needs more than her fans might think.

“One of my biggest issues with riding and driving is actually having low confidence,” Ali said.

When Ali has moments where she isn’t sure she is up to the task with a particular horse, Helen is always there to assure her that she is.

“I think it's easy to remember the good ones,” Ali said. “But I've fallen off in the ring so many times. I've had classes where I didn't rack at all. I’ve been the subject of so many gasps. My purple ribbons far outweigh my blue ones.”

Even today her trainer, Tammy Devore of Devore Stables in Sonora, Kentucky, is still working with her to improve her confidence. But, despite this ongoing struggle, Ali is happy to say that nervousness is no longer an issue for her.

“Two things keep me from being nervous,” Ali said. “One is remembering why I got into this to begin with. I love horses. It would be silly to stress them out by being nervous or not being grateful that I’m sitting on a horse. The other thing is you waste time being nervous. You sacrifice all this time or money. Other people can identify with the fact that you didn't get to go to the birthday parties or the sleepovers, and probably missed prom for it. But it’s an incredible opportunity, so I’m going to enjoy the hell out of it.”

One of the things she enjoys the most is the bond she forms with her horses. Of course her bond with Gumby, who died two years ago in her arms, will always be one of the most special, but Ali has a knack for creating meaningful relationships with all of her horses … sometimes whether they like it or not.

“I’ve always ‘forced’ my horses to be my buddy,” Ali said.

Starlight Voyager is the perfect example. Though he was difficult and didn’t want to befriend her at first, Ali was persistent, and she believes it made all the difference.

“I really believe that, in bonding with him, he's done more things for me than he wanted to or necessarily would have,” Ali said.

Her bond with Tigerlee made a big difference too – for Tiger, but also for Ali.

Ali spends some time with donkeys Sloopy and Schroder.

“When my mom had cancer and it got really hard for me I could always count on Tiger,” Ali said. “He was wild and game and tough but he would never, ever hurt me. And if you walked into his stall crying he knew.”

These days Ali serves as president of Medallion Media Group, the publishing company Helen founded eleven years ago, but she is the same unpretentious person outside the horse world as she is in it; when she first came to Medallion, she started as an intern and worked her way up just like everyone else.

Medallion wasn’t her first experience in the publishing world, either; always ambitious, she became the first young adult reviewer for Romantic Times Magazine when she was just thirteen years old, and did some modeling for romance novels in her teen years as well.

“I don’t talk about that much, though,” Ali said.

Today she has set aside the reviewing and modeling to focus on bringing peoples’ art into the world for the enjoyment of others. Some days this means she is approving and giving opinions on cover art, and sometimes it means she is deciding which trade shows will be the most appropriate for Medallion’s products that year.

“Quite frankly, I have an unbelievable team of driven, brilliant people and I often feel like my role is primarily supporting and encouraging them,” Ali said. “I give out some ideas, but they make the magic happen.”

To Ali, a successful day at Medallion is a day when someone picked up a book, because she believes in the power of books to transform, elevate and bring good to the world. But she works to cultivate good in other ways, too, and with something that might be considered a little less conventional – jewelry.

Though Ali began making her own jewelry in high school, it didn’t occur to her to turn this passion into a business until years later when someone gave her a special crystal.

“I swear it made me happier, and I started getting into the idea of crystal healing,” Ali said.

Combined with her love of jewelry, this formed the basis for her new company, Luna Avalon Designs, which launched in February of 2014.

“I love it because I get to be creative, which is extremely important to me, and it’s fun,” Ali said. “Why wouldn't you want to have a business that makes people feel better?”

Ali and her friend Lexi Strauss brought Ali's Luna Avalon Designs to this years American Royal.

And, while jewelry may be a very human concept, animals are never far from Ali’s mind, as she donates ten percent of all Luna Avalon proceeds to rescues, a mission she holds dear to her heart, and one of the biggest passions she shares with her mother. The other, of course, is the horses – something that Ali will forever feel privileged to call part of her life.

“That is the first thing I think of when I wake up in the morning,” she said. “I'm not going to say I couldn't be more appreciative because you can always be more appreciative, but I constantly think, ‘How amazing is it that I'm healthy enough to do this, and that my mom is able to put me in these positions?’”

Most people in Ali’s position would get used to the view, but it is likely that the gracious young woman with the bright red hair never will. She is simply Ali, and when she reflects on her life, to her, just like her trips into Freedom Hall, it is breathtaking, every time.

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