Jimmy, George & Close Calls

The Working Student Chronicles Part II

I learned a lot at Jimmy’s. Later, I referred to it as my “Graduate School” and I don’t think I was wrong. Five years of grad school to be exact. One of the best things Jimmy did, for everyone who had horses at the farm, was to create a daily schedule for each horse starting with the three day event and working backwards by about three months. He started with the galloping days first, then plugged in the jumping days, the flat days and the hacking days around it. I also kept a journal and tracked what we did to accommodate the inevitable changes that occurred due to unforeseen circumstances such as lost shoes.

On top of providing a schedule, working students at Jimmy’s had a lesson every morning at 7:30 or 8:00 a.m., five or six days a week, without fail, before any of his other lessons started. I really commend Jimmy for this. Even if it was just knocking us out before he started teaching his paying clients for the rest of the day, I always viewed it as putting us first. I think it was a combination of both things, but I was eternally grateful for all of the time and expertise he poured into his working students.

We did barn chores before our lessons and made sure the barn was immaculate before we tacked our horses up. This included sweeping the entire barn by hand with small brooms. A hot little tip: We poured a quarter of a cup of Pine-Sol into a garden watering can and filled it the rest of the way up with water. Then we went down all of the aisles in the barn making big loops as we went. It looked like a series of infinity signs from one end to the other. This made the barn smell really nice.

Jimmy always said the mark of a top barn is that it doesn’t smell like a barn.

Jimmy was also a proponent of being very fit as a rider and he gifted his working students with a membership to the small, local gym in town. Not only that, he expected you to use it every day. This was not a hard ask. I was happy to comply. Sometimes we would see him there and he never failed to walk up to my treadmill and adjust the speed accordingly. “Why are you going so slooow?” he’d ask, with his finger pressed down on the speed button.

Other times we would see him first thing in the morning for our lessons and the first words out of his mouth were, “I didn’t see your name on the sign-in sheet at the gym yesterday. What happened?”  I’d protest vehemently because we went without fail. I wasn’t sure if he was bluffing or instigating a wily ruse. The fact was, Jimmy was keeping tabs, and it mattered to him. If he ever caught you swinging around in the saddle on course gulping air (he watched with binoculars), he would double down on you.

I had been there for almost two years when my mom came for a short visit. The second night she was there, I had been invited to a party at another farm. I wasn’t planning to go anyway, but my friends kept asking me if I was going, and finally, I asked my mom if it would be okay to go. “I’ll only stay two hours,” I promised. She was fine with that. The party didn’t start until 9 or 10 p.m., so the two of us had already eaten dinner anyway.

A friend came and picked me up and off towards Middleburg we went. Two girls, both longtime students of Jimmy’s, shared a barn apartment and decided to host a big party. Everyone was there. We had a blast. The night wore on and I lost track of time. At one point, I curled up on the driveway while waiting for my friend to find her shoes, which had been missing for most of the night (she didn’t find them).

Using what judgment we had left, we caught a ride home. At promptly 3:30 a.m., we pulled into the front lawn of the cottage and someone opened a door and rolled me out. There was a quick, “Are you okay?” before the front door swung open with my mother gripping the doorknob accessing the situation. My fellow passengers registered her anger and quickly rolled their windows up and peeled out.

I had the wrath of my mother who was so disappointed at first, and then downright pissed.

She spit at me, “Where have you been?! You were supposed to be home four hours ago! I was worried sick!”

I was trying to take it all in and perfect my alibi, which sounded plausible in my head.

She continued. “I called Jimmy because I was so worried and didn’t know where you were. I was about to call the cops!”

I remember thinking “Ahhh…fuck…meee…” which I kept to myself. I could see I was never going to make any headway with the spewing volcano that was my mom, and looking at my watch, I had to be up in two hours, so sleep was my immediate priority.

When I woke up, I saw that my alarm clock did not indicate a time whatsoever. In fact, I soon found out my alarm clock was not plugged in to the wall. I was pissed. I was pretty sure this was my mother’s retribution. Her way of making sure I paid for my debauchery.

Except, I’ve always been a morning person. I woke up twenty minutes before my lesson. I threw on riding clothes, ran to the barn, threw feed to all of the horses, and swept what would be visible as Jimmy got out of his truck and made his way to his office.

George was in the cross-ties when Jimmy pulled up. I leaned over with my hands on my knees trying to slow my respiration down after the morning’s sprint of chores. When Jimmy walked into the barn, I said very chirpily and nonchalantly, “Morning, Jim. I just have to throw my saddle on and I’ll be ready.”

Jimmy went into his office like clockwork and laid down his bag. I was throwing my saddle on George when Jimmy walked back out and came right for me. Stopping right next to me, he put his arm around my shoulder, squeezing me tight. Wearing a shit-eating grin on his face, he pulled me close and said, “Now how about we take those stirrups off of your saddle? What d’ ya say?” He gave me one more squeeze for good measure, smiling even brighter into my ashen white face.

That’s when I remembered.

Ahhh…fuck…meee,” I thought to myself, yet again.

Another time, I dropped Jimmy off at the airport on his way to teach one of the many clinics he taught all over the country. Jimmy liked to use their old, well-kept Mercedes station wagon for these outings so it would get some use. Otherwise, it lived a well-preserved life in the garage. I loved driving that car. It was diesel, and though it took a bit for it to react to you stepping on the gas pedal, once it started to go, it really took off.

After I dropped him off, I drove back to Middleburg and picked a few girls up for dinner. We had planned a “civilized” dinner out at the Olive Garden and I offered to drive. Yes, this was against the rules, but I figured it was an innocent outing. What harm could come of it?

I drove down the short gravel road to my friend’s house. Everyone clambered in and we turned around, and left. As I was driving back down the gravel road, chitchatting with my friends, I noticed something moving on my left out of the corner of my eye. I looked over and there was a riding mower peeling across a guy’s lawn heading straight for us. The problem was the guy wasn’t on the mower…he was chasing it. I hit the gas, but like I said, it took a while for the car to react. At the last minute, the car took off, and the mower narrowly escaped hitting us. When I looked in my rearview mirror, the guy had caught it in the street and was waving an apology at us, smiling like “no harm, no foul!”

After that, my legs were shaking and you could have cut the tension in the car with a knife. We were all speechless. We were shook up, but not so shook up that we didn’t go to the Olive Garden. We did. But I never took the Mercedes for any extracurricular activities after that.

Speaking of pulling the stirrups off our saddles (for repentance), every winter Jimmy conducted two-weeks of longe lessons. We longed each other every day rotating horses. The beginning of each lesson consisted of vaulting on to the horses from the ground. Jimmy gave you three tries before he’d give you a leg up. With your left hand on the withers and your right hand on the pommel, you hopped in place a few times before trying to pull yourself up.

If I had one claim to fame at Wofford’s in all of my years there, it would be this. Once I figured it out, I was the only one who could climb on the horse each day from the ground. (Unfortunately, sometimes you don’t get to pick what you’re good at!). Notice I didn’t say I “vaulted” on. That might have been the goal, but climbing and flailing yourself up counted.

The trick was getting your shoulders across their withers. If you could do that, you had a pretty good shot. The other trick was to get it done on your first attempt. Every jump-up sucked the energy and strength right out of you. Usually by the third try, the rider would only accomplish half of what she did the previous two tries.

We did all kinds of “tricks” on the longe line including riding side saddle at the canter and doing sit -ups. Jimmy said he knew whether or not someone would go advanced by the way they did, or didn’t do sit-ups. I heard that and was determined to nail it. With our arms crossed over our chest, we leaned back and touch our helmets on the horse’s croup, before popping back up and touching our noses on the horse’s neck. Again, there was a trick to it. To be successful, you used the horse’s movement to help you pop back up from their croup. The rest of it took a little bravery and a lot of concentration.

Side-saddle consisted of swinging one leg over their necks to rest in front of the pommel. This exercise was all about balancing in the middle of the saddle at the canter with no ability to grip the tack. Yes, one hand held the cantle and the other the pommel, but if you weren’t in the middle of the saddle every stride, your arms weren’t going to save you. Sometimes a rider would lose their balance and have to bail. As Jimmy said, “Just make sure you jump off on the same side your legs are on.” Sounds self-explanatory, but one time, it didn’t happen like that, and it was horrible to see someone fall off backwards with their legs up in the air. That one knocked the wind right out of her.

I loved the annual longe lessons, but they sure did make me incredibly sore (the good kind of sore!). We finished every lesson by doing a back flip off the side. This sounds crazier than it was. Sitting in the saddle, we would put both of our legs on the right side of the horse and flip them up over our heads to land on our feet. Sounds easy, right? Not always. Sometimes I landed on my ass when I couldn’t control my momentum. More than once, on my way over and down, I slapped Jimmy across the face in the process. He was always one of our spotters for this exercise.

Shaking his head, he’d say, “Every fucking year, Jenn. Every…fucking…year.”

Our main job at Wofford’s was taking care of his wife’s fox hunters. She was a joint master at one of the local clubs. This meant she hunted three days a week. Days the horses weren’t hunting, she provided a strict exercise schedule for all of them. They did a lot trot sets and hacking in between their hunting days. She had six or seven hunters in the barn at any given time so ideally each horse wouldn’t have to hunt more than once every two weeks.

Jimmy was a stickler about a few things regarding turn-out, such as the buckles on your spur straps being positioned directly in the middle of the front of your boot, but Jimmy’s wife had the corner on turn-out.

 She was always immaculate in her riding kit, and she expected her horses to be turned out just as well. I learned a lot from her on how to do this. Every hunting day, we would bathe and braid the horse, put tack on him, cover him with a scrim sheet, and load him on the lorry we would bring up to the barn the night before. Once the horse was loaded, we put a folded towel in the lorry for wiping snotty noses or dirty boots, as well as a sponge with a generous squirt of Lexol added, to wipe off tack off when they arrived at the meet in case it accumulated any dust on the way.

The first three day I competed at as a working student, with Jimmy as my “official” coach, had not gone well. I pulled George up on the cross country because he was exhausted. Upon examination back at the farm, we found out George had allergies and had developed Heaves. We spent the winter rehabbing him back to good health. When the spring rolled around, George was good to go and we were on track for the Essex Three Day Event. 1996 turned out to be a great year for my riding. George clocked around Essex, and later, the Radnor** in the fall.



But we all know what goes up must come down (especially with horses). The following year had some peaks and valleys. T-Bird was on the way in as an up and coming prospect, while George was thinking the Advanced level might just be too much. Sometimes you don’t know these things until you knock on the door.

I decided to switch tracks for George and concentrate on his show jumping. He was a good jumper and rarely had a rail in his career. A young professional liked him and wanted to take him on the cuff. She agreed to pay all of his expenses and get her money back at the end. Honestly, that’s what I could afford to do, aka none of it, so I agreed. She was located about an hour and a half away and took George to her farm.


Like most things, it started out great. I got lots of reports and videos, and George was going well. But the reports became farther and fewer between, and soon, it was radio silence when I reached out to her. Another student at Jimmy’s had sent her horse elsewhere to be sold around the same time. One day, she came into the barn very serious and said, “You won’t believe what happened yesterday.”

We stopped in our tracks and waited for her to continue.

She said, “Apparently one of the neighbors was shooting their gun, and a bullet ricocheted from out of nowhere and grazed the inside of Hobbes leg in the field.”

We stood there speechless.

I said, “So what you’re saying is your horse got shot by a random bullet.”


We stood there dazed, catching flies for a minute, trying to reconcile what she just told us.

And then I panicked.

I thought of my horse, George, somewhere at a farm, with a girl who would not call me back, and I thought the worst. Did she sell him and not tell me? Is he hurt and she won’t tell me? Did she move him elsewhere, with someone else, and not tell me?

The student’s horse did end up being fine. The bullet miraculously went through muscle, so he needed some stitches and time off, but he made out like a bandit as far as that goes.

In the meantime, I hatched a plan. I drove up to the farm where George was, late at night, dragging my boyfriend with me. I told him I needed to pick up a horse. When we got to the entrance of the farm, I killed the headlights.

My boyfriend looked at me from the passenger seat. He said, “What. Are. You. Doing?”

I locked eyes with him.

She doesn’t know I’m coming.”

Hooo-ly shhh-it. Are you telling me that we’re stealing a horse?”

I said, “Ya can’t steal what you already own.”

We crept down the driveway with no lights on, going very slowly. I had never been to the farm, so I watched the cottages for any signs of life. When I got to the barn, I turned the rig around and put the ramp down.

I left the engine running.

I couldn’t find the light switches in the dark. The horses, surprised by the intruder, started to stick their heads out of their stalls, snorting at me. I could only catch a glimpse of their faces when they turned toward the moon. About five stalls down, I found one with no markings, and putting my hands on that narrow face, I recognized George immediately. I slipped the halter I brought over his head and pulled him out of the stall. I stripped him of the multiple rugs he was wearing and took him out to my trailer where I threw two heavy wool coolers on him. It was cold enough outside, I wasn’t sure if they would be enough to prevent him getting chilled, but that was going to have to do. Sure enough, George loaded straight away and I carefully lifted the ramp, trying not to make a sound. We crept out of the driveway with no lights and headed back for home.

This is why I rarely bartered in my business. Someone always loses.

I called the girl the next day, and lo and behold, I got her on the phone straightaway. Of course she was pissed. I told her the truth. She had avoided my calls for almost three months and I panicked. She rattled off all of the money she had spent on him out of her own pocket. Herein lies the problem with bartering.

In the meantime, I got a call from someone who had transitioned from Eventing to Steeplechasing. She was an assistant trainer to a very successful trainer and jockey who trained for a high-profile, prolific owner. She said she remembered George from the events and what a good jumper he was. She thought he could be a Maryland Hunt Cup horse and wondered if I would let them try him. My interest was piqued. I said sure. I drove the horse north for them to try.

I warmed George up in the indoor and jumped a few jumps. Then they wanted to see him jump outside. The assistant trainer, the eventer turned jockey, hopped on. They slid the top board out of the paddock fence and she picked up a gallop next to the driveway and went down to it full blast. Then they put the board back up. She looped around in the field and galloped back down to the paddock fence at a really good clip. I would be lying if I said I didn’t have my eyes squeezed halfway shut as she neared the fence, but George sailed over it and that was that.

They needed a couple days to think about it, but when they came back to me, they offered me a year’s lease for half of the purchase price of George. Even though it was considered a lot of money at that time for a one-year lease, I just couldn’t stomach the thought. I envisioned him being handed back to me crippled and wrecked, or worse. I declined.

However, they had planted a seed in my mind. I decided to call a successful steeplechase trainer in Middleburg and see what he thought of George. He said to bring him over. I shipped George over and three of us hacked down the long gravel road until we got to a neighbor’s fields. We picked up a trot and were talking smack and bantering a little before they started to canter. We all had a little canter, before the trainer turned his head around and said, “KEEP UP!”

And then they took off.

In less than two seconds they put a decent gap between me and them.

I thought I was already going fast.

So I went even faster.

We galloped up and straight down hills, looping back and forth over the countryside, absolutely flying. My eyes were watering so badly, I had to keep blinking to see, and it didn’t take long before my quads and my shoulders were burning. I couldn’t have pulled up if I tried. All in all, the galloping probably only lasted four minutes, but that moment has stayed with me to this day.

It was the first time I thought, “Hmm, I wonder if I should be a jockey.”


The trainer agreed to help me with George. We swapped horses. He pulled a gelding out of the field that needed to be reschooled and sold. I took “Shorty” back to Jimmy’s and George went to live at the racing barn. I also helped gallop a couple of horses in the morning as part of George’s keep.

Photo credit: Douglas Lees

I had been galloping there for less than a week when the trainer put me on a very seasoned campaigner. This horse had won on the flat, and over brush and hurdles, with multiple amateur owners. If there is such a thing as a steeplechasing schoolmaster, this horse was it.

Three of us hacked down to the Middleburg Training Track to have a gallop. I was supposed to stay behind the two horses I was with and just follow their lead—go when they go, pull up when they pull up.

We picked up a trot, and my horse’s neck got shorter and shorter, and pretty soon his ears were in my face. Instead of trotting, he decided cantering on the spot was more efficient. I crept closer and closer to the two horses in front of me. One guy turned back and yelled, “You’re too close! Get off my horse’s ass!”

I didn’t even have a chance to respond. My horse saw a gap and he was gone. We split between the two horses, both of those jockeys screaming at me, and we were off. I couldn’t hold one side of him. Pretty soon we weren’t galloping, we were breezing.

Big diff.

The little bay gelding galloped with his ears in my face and I still think that’s the fastest horse I’ve ever ridden. He was the epitome of a good thoroughbred—fast, tough, with a superior work ethic. I’ll admit, I was scared. I knew I had no control, and I wasn’t following orders.

If this horse got hurt, it was on me.

By the time we had galloped over the backside, I was beyond my quads and shoulders burning. They had smelted into solid metal. The horse kept going, past the ramp onto the track. The trainer was standing just beyond that on the rail. I looked at him like “I have no fucking control and don’t know what I’m doing,” but he was standing there with a smirk on his face, holding a stopwatch in one hand and giving me a thumbs-up with the other.

We galloped past him, still flying, and when we got to the 1 mile pole, the horse pulled himself up as easy as he pleased. He knew his job and where the finish line was. We trotted a bit before turning in and heading back to the ramp to leave. I was so tired I couldn’t form words. The trainer just laughed all the way back to the barn.

I spent the winter racing in the Fox Hunter’s Timber races at the point to points in our area. I remember being so excited to tell Jimmy that I had finally found my perfect sport, the one where it was always “three long and never four short!” If I had a nickel for every time Jimmy screamed at me “Jenn, if it’s between three long strides or four short ones, it’s always four short!”  I’d be rich!

It was an incredible experience. George had a great gallop and it was easy to see a distance on him, even going that fast. More times than not, he lost the race down the home stretch, and I suspect this is where his age caught up to him. That said, he was also just a cheap claimer from Arizona competing against stakes winners. He did a great job holding his own considering the competition.

During my tenure at Wofford’s, the Kentucky Three Day upgraded to a four star. A friend of a friend offered to fly four of us to the event for cross-country day. We met in the wee hours of the morning when it was still dark. We pulled the car up to the hangar at the little airport in Manassas. The pilot slid the door up and proceeded to wheel the plane out onto the pavement using one finger.

I wanted to throw up.

It looked like a Ford Fiesta with wings.

I boarded, but not happily. It was a quick, uneventful flight, and we landed before the rain came through. We had a great day walking around the course, drinking a couple Heineken’s out of a can, and watching fabulous horses and riders at our country’s first four star event. We even made it home safe and sound.

In the meantime, one of the girls in the cottage was given a cat by a friend of hers attending UVA. Apparently the cat was no longer welcome at the frat house. We weren’t allowed to have pets in the cottage either, but the cat needed a home, so how could we say no? Stimpy was still more kitten than cat. She was tiny, gray, and mottled brown. I wouldn’t call her a looker, or even cute, but she was an awesome dog cat. She had survived living in a frat house, so living in the country, even in secret, was a serious upgrade. We left a back window open at night for her to come and go as she pleased with the intention of keeping her locked up during the day.

Being a survivor, she was good at taking care of herself. Never sure where her next meal was coming from (even though she always had cat food available) meant that anything left on a plate, or in a bowl, or in a glass, was fair game. I caught her on the counter many a time with her head shoved all the way down in a tall glass licking up the remnants of what was once milk. Stimpy would eat and drink anything.

It didn’t take long for us to notice that Stimpy was filling out in her newfound cushy lifestyle. Turned out our kitten-cat was actually preggo. She soon had two kittens of her own, a grey female like her and an orange tabby male. Since we had been so successful keeping Stimpy under wraps, we decided we could keep all three.

That is until Jimmy’s wife popped her head into the cottage unexpectedly and found all three.

Somehow we managed to keep all of the cats, even as we went our separate ways. One of the girls kept the female, whom she named “Nermal,” and I kept the male, who I called “Smithers,” or “Smitty Kitty” for short.


After five years, my working student gig came to an end. It was time to strike out on my own. They say it takes 10,000 hours of practice to perfect a skill. That’s 10,000 hours of “perfect practice” (Jimmy’s term) riding horses before you are adept, let alone good, at it. An average person works 40 hours a week for 50 weeks a year. That comes out to 2,000 hours of working a year. I certainly didn’t ride horses 40 hours a week straight at Jimmy’s, but I soaked up whatever crumbs of knowledge I could in whatever way I could for more than 40 hours a week.

Anyone can hang a shingle out and call themselves a professional.

But have you done the work?

It was such a great experience working for Wofford and being surrounded by good horses and good riders. I am so grateful for all of the lessons and attention and expertise Jimmy gave to us. When David O’Connor told me at sixteen “if you want to be anybody in this sport, then you have to be in Middleburg,” he wasn’t wrong.

It was one of the best decisions of my life.


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