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Ali DeGray - People's Choice Junior Exhibitor of the Year

by Ann Bullard


World’s champion equestrienne. Those words only begin to describe Ali DeGray. She is an artist, photographer, editor, a person her trainer, Ruth Gimpel, describes as “an old soul, always intelligent and with an intuitive insight into life and people way beyond her years.”


If ever a person were born and bred to achieve such heights, DeGray certainly qualifies. The daughter of Helen and James Rosburg, niece of Misdee Wrigley Miller, granddaughter of the late Deedee Wrigley Hancock and great-granddaughter of the late William Wrigley, DeGray’s roots run deep in the equestrian world. James Rosburg’s career in sculpture and Helen’s as a romance writer and publisher have helped open different vistas for their daughter.


At 17, the petite redhead has climbed to the top of the Saddlebred ‘mountain,’ at least as far as junior exhibitors are concerned. Under Gimpel’s tutelage, she moved from being a seldom ribbon winner in academy to Louisville champion. In 2006, she won junior exhibitor world’s titles in the five-gaited, roadster pony and country pleasure divisions. After eight years in the saddle, she has garnered 23 world’s and reserve world’s championships with eight different equine partners.


Horse World readers recognized DeGray’s achievements by voting her the 2006 Junior Exhibitor of the Year. CH Tigerlee and CH Kalarama’s High Roller topped the voting in the junior exhibitor 14-17 five-gaited and junior exhibitor country pleasure divisions while Seize The Moment was reserve Junior Exhibitor Roadster Pony of the Year.


“I’m over the moon that people voted for me,” DeGray said when she heard of the award. “This has been the most amazing ride of my life. I’m eternally grateful for everyone who supports me and is my friend.”


Looking at DeGray today, one might think it all came easy. That would be anything but the truth. The Rosburgs spent many hours on the road between their home in Palm Beach and Gimpel’s stables in Lutz, Fla.


“Ali started with me when she was eight. She had been thrown by an Arabian and was really afraid,” Gimpel said.


DeGray’s ‘up-down’ lessons began with Gimpel running next to her. She progressed to walk and trot academy classes and on to Gambler, an academy horse leased from Michelle Maynard. When DeGray was ready for a horse of her own, her parents selected the pleasure driving pony, Among The Stars (Hoppy).


“Ali was so little when she started, we had to put a feed bag in the bottom of the pleasure driving cart,” James Rosburg said. “She probably didn’t weigh 50 pounds.”


They started well, coming back to win the stake after tying reserve in the qualifier at the 1998 Harvest Days Horse Show. The following spring, DeGray and her mother shared the pony, with DeGray getting ribbons at Gasparilla and Helen winning a pair of classes at Tampa Charity.


That year was a break-out season for Pixie Dust and Steel, Inc. The Rosburgs had become immersed in the saddle horse business, with both Helen and James having horses to ride and drive. There was no question that the group was headed to Louisville. DeGray and Among The Stars brought home two ribbons – one green and one brown.


The year 2000 brought new opportunities and new honors. Teamed with the proven Somersby, DeGray went through most of the season before winning her first blue at Southeastern Charity.


Gimpel laughs when she talks of the decision to take pair to the world’s championships the following year. “I told Helen, ‘Now, Helen, Ali is not ready to go to Louisville and compete in Junior Exhibitor 13 and Under.’ She told me, ‘If you want to take my child to Louisville for experience, you take her. Why in the world would I want her to go to Louisville her first year under saddle and be real competitive? She doesn’t have the right to go and be competitive. She has to earn that.’”


DeGray spoke about her first – and always beloved mounts. Hoppy has since been sold, but DeGray agrees she could not have asked for a better pony.


“Somersby is still my baby,” she said of the horse leased by the Harvey Greenburgs. “He’s still ornery. He will try to buck me off if I ride him and he thinks that is hilarious. He may be overweight and goofy, but I think he’s one of the most beautiful horses ever.”


As DeGray’s skills developed, her parents and trainer challenged her with new mounts. First came Free Willy, arguably one of the best roadster ponies in history. Pixie Dust and Steel’s white silks with red trim graced winner’s circles from Florida to Kentucky, including a pair of 13 and under world’s and champion of championships titles and a world’s championship and reserve champion of champions in the 14-17 age group.


Such horses as I’m Good To Go, Autumnwood’s Rumor Has It and Reedann’s Whispering Leaves followed. DeGray continued to hone her skills, never anticipating what lay ahead. Gimpel matched her with the proven CH Token Favorite, her next step in learning to ride a five-gaited horse.


In early 2005, the Rosburg family and Gimpel headed into a cold Kentucky winter to shop for horses. They looked at four before meeting Melissa Moore on what Helen called “the nastiest, coldest, rainiest day.” All had seen World’s Champion CH Tigerlee in the show ring.


“The first time I saw him [at the barn] I was star struck,” DeGray said, speaking of the horse as well as of Donna and Melissa Moore. “They brought him to the ring. He was huge. I couldn’t believe I was looking at him and would ride him.”


“Ruth said Ali could ride him, so I knew she could,” Helen said, adding to the story. “When Melissa rode him, I was thinking ‘Oh, my goodness.’  I was nervous but trust Ruth so completely I let Ali get up on him. She got on and the hair on my arms stood up! It was just electrifying!”


Plans were that Gimpel would show Tiger throughout that first season. Those changed after Asheville. In early June, DeGray stepped up on her five-gaited powerhouse at Chattanooga Charity. Many observers agree that ‘electrifying’ is a good description. They earned a blue and reserve at Lexington and then it was time for the World’s Championships.


“We just decided to go for it,” James said.


DeGray and Tiger left Louisville with a tricolor signifying their being the best in the 2005 junior exhibitor 14-17 five-gaited division.


The year 2006 brought many changes for DeGray and her family. They had moved from Palm Beach to the Tampa area to be closer to their horses.


“I think Ali now is as good a junior exhibitor rider as anyone,” Gimpel said, crediting DeGray’s being able to ride close to home as one contributory factor. “They lived a five-hour drive from here and she couldn’t get the hours in the saddle she really needed. Ali has worked her heart out.”


What seemed would be a comparatively easy year proved to be the greatest of challenges. When Helen was diagnosed with a recurrence of breast cancer, everyone’s focus changed. The Rosburgs and their extended family carried on with the grace one has come to expect. Not only was DeGray facing her senior year at a new high school with all that entailed, she had to step up and help be a rock for James and Helen.


“She is so careful of me,” Helen said, speaking not only of the past year but throughout their lives together. “Being her mom, I feel so loved, so cherished all the time. She looks out for me and worries about me like I worry about her.”


Neither Helen nor DeGray speaks much about those difficult times. A visit to the Medallion Press Web site gave a little insight into some of the teenager’s days.


Helen wrote, “When he [James] was unable to care for me, Ali stepped in.”


DeGray’s care provided her mother, “some of the lightest, funniest moments of my life. Ali, for instance, was there when the drains came out.


“It was kind of like a car wreck. You don’t want to look, but you can’t seem to look away. She paled. She stood behind the medical assistant, peeking first around one side, then the other. I concentrated on her expression as the tubing was swiftly pulled out. Ali's features might have been made of rubber they contorted so dramatically. I laughed so hard I was only vaguely aware of the messy follow-up and the discomfort. I didn't think anyone could be funnier about it…”


“This past summer was very difficult,” DeGray conceded, emphasizing only the horse-related opportunities. “I had to step up in the show ring in Mom’s place. I showed Seize The Moment for her.”


She also took over the reins of Kalarama’s High Roller at Lexington, winning the junior exhibitor country pleasure title. They followed that with a pair of wins at Louisville, then with victories at ASHAV and Harvest Days. When Helen is ready for her favorite horse, DeGray happily will relinquish that opportunity; meanwhile, she is a more than able ‘catch rider.’


While it may be difficult for some to understand DeGray’s progression from a timid, beginner rider to one who has mastered a powerhouse like CH Tigerlee, watching her mature into the confident young woman she has become has been even more rewarding. The timid little girl wearing round glasses, the youngster who clung to her mother’s skirts (or jodhpurs) now is a confident young woman and freshman at the University of Tampa. DeGray will be 18 in July, which not only gives her one more year as a junior exhibitor in the show ring, but makes her younger than most of her college classmates.


“I’m a little young to be in college,” she said. “I took some tests, went to summer school for two weeks and skipped my sophomore year in high school.”


As an art major, “I get to do art all the time. I’m still intrigued by anthropology and history, but art and horses are my two major loves at this point in my life,” she said.


DeGray plans to finish her undergraduate work at the University of Tampa. She speaks of attending NYU or the Art Institute of Chicago for graduate school. Meanwhile, she will “stick around, ride horses and stay with my mom.”


A self-proclaimed ‘nerd,’ DeGray revels in editing manuscripts in the horror genre for her mother’s Medallion Press. “I get to read all the time, so I’m happy about that. On the inside, I’m very, very nerdy,” she explained.


DeGray’s earlier association with the publishing company included modeling. If you look closely at several book covers, you will see her with some of the most popular male models in the business. Today she includes conventions and editor appointments in her routine. She also is a typical teen who enjoys her horses, drawing, skate boarding and water sports.


She spoke briefly about being Helen and James’s child. “It’s awesome, being Mom’s daughter. She is more my friend than my mom. It’s cool riding together. She never pressures me but encourages and supports me. She makes fun of me from time to time, but it’s okay.


“James is the best horse show dad that ever existed. If it weren’t for him, I don’t know where any of us would be right now,” she added.


“Ali’s the best kid in the whole world,” her mother said. “She is so responsible and conscientious and has the healthiest conscience of anyone I’ve ever met. She can’t stand to feel guilty so she never does anything wrong. She lives the axiom, ‘let your conscience be your guide.’”


With her final year as a junior exhibitor ahead of her, DeGray looks forward to sharing the show ring and spotlight with her friends.


“Any way the ribbons go, I’ll be happy,” she said of the deeply-competitive division. “We’re all friends and they’re all great riders. I have so much respect for everyone in that class. It’s an honor to be among those people.”


Win, lose or draw – the upcoming season will be an exciting one for DeGray, her parents, trainer and all who revel in the talent of the American Saddlebreds and their young riders.

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