Jamie
Pestana
At 23, Jamie Pestana has achieved what many people only dream of. Her achievements have not
come without their challenges and Jamie has had to be inventive with her training numerous times
throughout her career. The last few months Jamie has been preparing for the Grand Prix in nothing
but a bareback pad as she has been waiting for her new saddle to arrive. The Equestrian learnt
however this hasn’t been the first time Jamie has resorted to the bareback life as she recounts her
story.
A life of horses
“I was fortunate enough to grow up with
horses in my life,” Jamie recounts. “My mom is
a dressage trainer and until I was 10 we had
our own horse property, so my “babysitter”
was my pony!” Jamie got her first pony when
she was only two years old, a Quarter Pony
named Appleblossom. She would ride her
for hours while Her mum taught lessons.
“Apparently the only time I cried was when I
was taken off of Appleblossom!” She laughs. It
wasn’t long before Jamie got her first “dressage
show pony”, a three year old ConnemaraArabian cross named Darby. She was only five
when she got Darby and she recalls that he
was very naughty, and credits him with really
teaching her how to ride... and how to fall! “I
spent about as much time on the ground as
in the saddle in those days, but over time my
stubbornness prevailed and Darby was my first
training project. By the time I had outgrown
him when I was 11, we had shown through
third level together and he had given me a
foundation for training horses up the levels.”
A star partnership
Most of Jamie’s major achievements in
dressage have been enjoyed with her current
horse who is appropriately named Winzalot,
known as Winny to friends. Their record in the
Junior and Young Rider divisions is impressive.
In 2010 they were North American Junior
Young Rider (NAJYRC) gold medalists in the
Individual and the Freestyle classes, her team
clinched the Team silver that year. That same
year, the pair were also the Junior Young Rider
champions at the United States Equestrian
Federation Festival of Champions. In 2012
they were a part of the Young Rider team at
NAJYRC which received Team silver. In 2013
they rounded out their Young Rider career by
bringing home the Team gold medal and two
silver medals in the Individual and Freestyle
divisions. Recently, Jamie and Winny have been
schooling all of the Grand Prix movements in
preparation for showing in the Under 25 Grand
Prix division next year. “For me this is probably
my greatest accomplishment because he is
the first horse that I have trained to Grand Prix
myself,” she says proudly.
Overcoming adversity
Jamie’s parents bought Winny for her sightunseen at the recommendation of Dennis
Callin when she was 14. “We imported him as
a three year old as a resale project while my
previous horse, Elite, was injured. Elite was
older though, and Winny ended up becoming
such a great partner for me that we kept him.”
He has a very strong personality so training
him was not always easy, but he is incredibly
smart and loves to work. In 2010, when he was
only six years old (the youngest age horses
can be to qualify for Junior Young Riders) he
was both NAJYRC and National Junior Young
Rider champion. “We went on to have success
in the Young Rider division