The Best of the Best – Part Two: Being a professional is not all fame, fortune and glory


Hillary and D’Orsay (Harry) showing “under the oaks” at Upperville. I was glad to be invited to be a part of their exciting day.

I took a day off this past week to attend the nation’s oldest hunter/jumper show, the Upperville Colt & Horse Show. It is a prestigious competition held on absolutely stunning grounds in northwestern Virginia. It brings together the “best of the best” once again, most of them straight from Devon.

My dear friend Hillary was competing that day, crossing yet another thing off her bucket list. I was glad I could be there to see her show (and to head up her personal gaggle of paparazzi!) but also to watch some of the most accomplished horses and riders while dreaming about how good I would be at living like the top 10%.

After a full 10+ hours of watching hunters show “under the oaks” in the main ring at Upperville, I had one serious take-away:

It is not a glamorous life to be a professional rider/trainer at that level.

Of course when I was a pony rider and even in to my early junior years, I thought that there would be nothing more exciting and fabulous than competing in the Olympics and then becoming one of those trainers you only read about in The Chronicle of the Horse. Luckily for my parents I became more realistic about my future, sadly for us all I went in to politics. Sure, I trained for a few years on the side, basically to pay a couple of horse bills and because I truly do enjoy it. But it was never going to replace my day job (even though sometimes it did.. shhh!). Which means I understand completely why these men and women have picked this career path.


Bones wasn’t super impressed with the Green Conformation Hunters, but he guarded our spot in the grandstand from the rogue Corgis, Jack Russells and other horse show canine ruffians like a champ!

Back to Upperville.  I sat in the grandstand with my dog for hours and hours watching the most winning hunter horses in the country compete against each other. I saw the most accomplished professionals put in perfect trip after perfect trip, usually riding at least two if not more horses in the same class. And those jumps were BIG – like 4’+ big in the High Performance Hunters. There isn’t much room for a mistake at that height. With a jumper a bad distance isn’t judged, so the only worry is taking a rail and accumulating penalties. In a hunter round, you better nail it right on the money every time because the jumps are big and the misses are penalized even without the obstacle coming down.

Wow. It was glorious. I loved every single minute of it!

As I sat there, well-dressed, well-heeled and really well-off owners came and went as they watched one of their many “investments” on course. I eavesdropped on as many conversations as I possibly could – it was simply irresistible. I learned that one horse really didn’t deserve the ribbon it got at Devon in the Derby because it rubbed a rail. Another horse just hasn’t looked right since the beginning of March at WEF. On and on it went, with different configurations of people throughout the day. Absolutely fascinating.

I got to thinking about those professionals riding their horses.  Yes, I’ll say it – those poor trainers. What a lifestyle they have chosen, what a hard scrabble path they’ve come down to get to this level. It isn’t glamorous at all, and I’m not kidding when I say that I would never want to be one of them.

Sure, they have found a career and made some kind of living from their childhood passion. They figured out how to transition from pony-obsessed kid to world-class athlete. And yes, they get to be around horses every single day. But even I get sick of horses sometimes and I pay to do it, it doesn’t pay me to be there!

These professionals have immense amounts of pressure put on them every time they put their foot in a stirrup. The owners spend tens, if not hundreds, of thousands to win and expect a perfect performance with a blue ribbon behind it. At one point I wondered how the conversation would go between a particular trainer and some owners later at the barn – he had pulled up the horse in the middle of the course, a very good decision in my opinion as the horse didn’t look right. Would there be questions? Would the pressure be that much greater the next time in the ring? Or would there be understanding that not every day goes your way?

Professionals must quickly turn that diamond in the rough into the Hope Diamond. Often times this means risking life and limb on an untalented mount that is competing above its pay grade. Once they find and train a smart, forgiving, safe and competent horse, it is quickly sent off to an amateur with the resources to fly in for the weekend to show. Process repeat.

Trainers at this level, or most any level really, cannot have much of a personal life. Think about it – you start your season some time in December down in Florida for HITS Ocala or the Winter Equestrian Festival at Wellington. Slowly through the spring you make your way north as it warms up, with Lexington then on to Devon. Quick jaunt to Upperville before you are off to chase points across any number of shows to make sure to qualify for indoors. Brief stop with your kids at the end of summer for pony finals, and the next thing you know it is indoor season (and October already) so you find yourself at Capital Challenge then Harrisburg and on to the Washington International Horse Show. Home for about a month, but those horses need to get back to Florida by the middle of December to acclimate to the weather, so enjoy your month “down” and have a great Thanksgiving.

This isn’t glamorous, this is grueling. The owners and riders get to jaunt off to the islands for some relaxation during the holidays. Meanwhile the trainers care for and ride their horses, making sure that they stay in tip-top form for the next season of point chasing.

What happens when you or I feel sick or have a bad day? Not much, we stay home and don’t ride. Professionals aren’t allowed that option. Watch any pro long enough these days and you can tell what hurts by how they compensate in the saddle. Watch them jog their horses for ribbons and be glad it is the horse, not the rider, being judged for soundness.

I know, I know, don’t cry for me Argentina! It is the life they have chosen, but that doesn’t mean it is all fun and games. It is tough getting to the top of any particular field. It is even tougher staying there. But an advertising campaign never spooks at the green rolltop or dumps you into the natural oxer. A house for sale won’t come out of its stall lame for no particular reason and blow its chances at being Horse of the Year. You can still go to your job as a financial advisor with a broken leg from that skiing accident in Vail.

I’m not trying to say that our day jobs are always predictable or easy or that we don’t work as hard. I’m just saying that the grass isn’t always greener for those who make my horse passion seem so enchanting and I think it is far too easy to pretend equine professionals have the best job in the world.

So I’ll still go to every big horse show I can to watch endless rounds of top performance hunters put in flawless performances. And as I see their riders wince when they hop off a horse and climb aboard another, I will be both jealous that they are living a life totally immersed in everything equine, but also feel a bit sorry for them that life isn’t nearly as glamorous as it may seem to the rest of us.

me and hill banquet

Hillary and I at a Wisconsin Hunter Jumper Association banquet close to 20 years ago now (sheesh we’re old!) Still friends and still crazy after all these years!


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