By Jolene Last
Every story has a unique blend of excitement, intrigue, heartbreak, love, and humor. As horse lovers, we inevitably bring more than we expect to the mix. My story with Teddy isn’t over yet, but we have had quite the roller coaster ride so far.

Teddy was born as Crusin Ta Caiman in 2010. An off-track Thoroughbred (OTTB), he raced until he was six and then was retired and adopted into a hunter/jumper family, where they quickly realized that the hunter world wasn’t his passion. He loved to jump, but his anxiety was amplified in the show ring. After much consideration, his owner, Anna, decided he may be better off at an eventing home. She called my trainer, Rebecca Gall, who went to try him out.
Rebecca really enjoyed him and thought he would be a perfect addition to her eventing family, so she presented him to a few of her students, but no one was ready to get a new horse yet. This is where I came in – as her last option. To be fair, I was not actively looking for a new mount either. I had a sassy Quarter Horse/Paint with severe breathing issues that were not being resolved. I knew, deep down, that it was time for his retirement, so we set up a time to check out Teddy.
Anna and her family very kindly offered to bring him to my barn, where there would be fewer onlookers. They also offered not to be there while I test-rode him so I would not feel uncomfortable. I confidently stated that it was not necessary and that I would be fine with them watching – famous last words. Anna began by getting on Teddy, and after a warm-up, she popped him over a couple of fences. So far, everything about this test-ride was going wonderfully.

It was my time to shine. I got on, and we proceeded to walk, trot, and canter. All was well. Becca had us jump a couple of small verticals. She then asked if I wanted to try an oxer. Of course, I did. I picked up my left lead canter and aimed at our fence. I saw the fence… but I didn’t see any distance. I was positive that I was going to see it soon. The jump kept getting closer and closer. I remembered them mentioning that Teddy was more apt to take an extra step than to take a long spot, so I repeatedly told myself not to get ahead of him and stay tall if he chipped… he didn’t. I believe we left an entire stride out, and we supermanned over the jump. Now, at this point, I am super proud of myself for staying on and not humiliating myself by falling off.
However, it was also at this point that I realized that he was not turning left… like, at all. We proceeded to exit the arena, at a canter. This had never happened to me, and I was mortified, but I didn’t have time to dwell on it because I had to stop! I should also let you know that Dillon, my Paint, would have dropped his shoulder and bolted like a rocket, leaving me staring at his rear end, leaping and bucking in joyful bliss. Teddy, on the other hand, quietly pulled up and stopped about 20 yards away from the arena.

I sat there for a moment in stunned silence. I then turned around and realized that all sound had ceased to exist. I then saw four faces with open mouths and large eyes staring at us. I sheepishly smiled and said, “Well, I guess I just made everyone else uncomfortable.” Anna’s mom just sighed, “That’s our Teddy.” I am pretty sure she looked at her husband and told him to get the truck ready.
As I returned to the arena, Becca asked if I was okay, and what my thoughts were. Little did they know that the next words out of my mouth were going to be, “I LOVE HIM!” At that moment, I realized that Teddy had my back, and I had his.
I know what you are thinking: everything was perfect after that, and we lived happily ever after. I mean, our bond did get stronger, but we had some ups and downs.

Shortly after I purchased Ted, a dear friend called and asked if I knew anyone with a horse that needed to retire and be a friend to her daughter’s new mount, which was the perfect match for Dillon. He was only going to be a couple miles away, and would get to be spoiled with love and attention.
Unfortunately, we had a little mishap while unloading him, and I broke my wrist. This was a little blessing though, as I got to focus on bonding with Teddy on the ground, while Becca could put a month of training on him. During this time, we realized that turning left was not just an issue with me aboard. I believe my eye size rivaled Becca’s as she tried not to run over me on one occasion.
But that still wouldn’t rival the biggest trial we would face.
In the summer of 2020, I felt great. I was working out more, and gaining more confidence that I would be able to enter my first event with Teddy. Yes, I am that person who feels confident at home, and the moment I think of the show environment, I shut down, and nerves take over. But I watched Becca take him in a couple of shows, and I was ready for Starter, and darn proud of it.
One day, I casually mentioned to Becca and her sister, Leah, as we were doing morning chores, that my two front teeth hurt and my eye felt like someone was squeezing it like a stress ball. This went on for a couple of weeks, so I decided to go in and get it checked. I didn’t want to enter any shows until I knew what was happening. After a few visits with a few doctors, I was referred to a neurologist.
In January 2021, I learned that I had a brain tumor. At this time, we were unsure if it was the culprit for my symptoms, but it did mean that I had to visit more doctors. Teddy was definitely a source of comfort through the many trips to the doctor.
While I was on wait-and-watch for three months, a third symptom emerged. I was struggling with my balance. I noticed that I couldn’t walk in a straight line, and when I was standing, my legs would give out. This escalated the doctor visits, and it was quickly decided that the tumor was pressing on my balance nerve. Surgery was now necessary.

We were very careful at this point each time I would get on Teddy. One beautiful spring day, I got on, and Teddy walked in a small circle, which made me so dizzy that it tops the list as one of the scariest days of my life. I dismounted, and as I walked slowly back to the stables with my faithful steed by my side, I sobbed. Would this be the last day I ever sat on him?
Many decisions had to be made. I was desperate to be able to ride after surgery, so Becca and I sat down to discuss our options. One of Becca’s students and dear member of our Birchwood Eventing family, Jessica Doering, agreed to take Teddy, keep him in work, and show him until I was healthy enough to ride again. I had to wait until July for my surgery, so I was able to go to a couple of shows. I was fortunate to have help getting around the showgrounds as my balance issues progressed.
I had a successful surgery, followed by months of recovery. Of course, my first question at every single appointment was always, “When can I ride?” The day I got the okay, I called Becca, begging to come to the farm to get on. We had already established that I would not get on Teddy for my first ride, as he is 16.2-hands tall. So, my first ride back was on Chewy, lovingly offered by our friend and fellow Birchwood teammate Lisa and her daughter Olivia. You couldn’t wipe the smile off my face that day. Next step, Teddy!
The ride did wear me out, and I didn’t start consistently riding until the following spring. Since I wasn’t very strong yet, I asked Jessie to continue riding and showing Teddy for the summer. One year after my surgery, I signed up for a small schooling show. It was at this show that Teddy and I had a miscommunication, and I fell off after a fence. Teddy, though, was perfect; he stayed with me, wondering why I was lying on the ground.
Unfortunately, I suffered a pretty bad concussion. This was a moment of clarity: I needed to consider my family in conjunction with my riding dreams. Teddy and I were both comfortable jumping at home, but his nerves fed off my nerves in a show setting. I have watched and been in awe of dressage, so I decided to let Becca know that I was thinking about changing disciplines. And this was the best decision I’ve ever made!!

Since Becca wasn’t available to go to dressage shows as much as I would like, we discussed options for trainers. There are so many wonderful ones to choose from, and then I met my new dressage coach, Nicole Trapp. She was very open to what I wanted or thought I wanted to do. She also knew about my fears. After a couple of lessons, I entered my first schooling show. She said I was capable of entering Training Level, but with my last show ending in disaster, I wanted to just do Introductory Level.
I trailered Teddy over on Friday. I could feel his excitement, so I popped him on the lunge line. He proceeded to demonstrate his athletic abilities, and show that the racehorse in him still lives on. One of the riders casually mentioned to Nicole, “Look at that young horse over there.” Nicole looked over toward me; I smiled and shrugged my shoulders in apology, and she responded, “He’s 13.”
One of the many wonderful things about Teddy is that – once he gets the wiggles out – he is a sweetheart. I got on him, and I could feel his devotion and desire to do whatever I would ask of him. We won our classes that weekend.
Following that show, we moved up to Training Level. This time, we would attend a USDF-recognized show. I was debating even going, as my mom was very sick and in hospice care. My father insisted I go and have a weekend to enjoy. I did. I loved the new people I met and the beautiful horses I got to see.
I also got to watch a Century Club ride that brought me to tears. I listened to everyone’s dressage journey with rapt attention. They encouraged me to take pride in my own journey. It was this show that made me realize several things, the most important being that I am blessed with a horse that makes me happy. He aims to keep me safe. If I mess up, I will be okay. Maybe, just maybe, I can earn my USDF Bronze Medal, too. Maybe I will even be able to do Prix St. Georges (PSG) someday. This is fun!

In 2024, I was able to show Training and First Level. Through NEWDA, (now a chapter of the Wisconsin Dressage & Combined Training Association) our local Group Member Organization (GMO), we were year-end Champions at Training Level, Reserve Champions at First Level, and I won Amateur Rider of the Year. This is something that I never dreamed of, and I am so thankful for it. But the connection and joy I have with Teddy supersedes all of it.
This year, I pray that we will continue to strive for our goals. I would love to get qualifying scores in First Level, and venture into Second Level. I don’t know where our story will lead, but entering at “A,” with Teddy as my dance partner, is all that I need to say, “We are a success!”











Beautiful story…. loved it!
God bless your future ❤️
Amazing story of Teddy and owner. Both working through what life threw at them. Love it.
Absolutely beautiful.
God Bless you both and keep you both healthy and safe!❤️
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