Jordan Rapp, born July 28th 1980. Three weeks later, he went for his first open water swim (sort of) in the waters of Lost Lake in Brewster, NY.

Eighteen years later, he took first strokes of a different kind - in a rowing shell - on Princeton University’s Lake Carnegie. After a high school athletics career focused on squash and lacrosse, he began training for endurance athletics on a Concept II ergometer in the winter of 1998/1999.

Millions of meters and millions of strokes later, he was injured for the first time in his rowing career while training to make the U.S. National Team. And so, in April of 2003, he clipped a pair of aerobars onto his road bike, bought a pair of aero wheels with the first tax return of his post-graduate career, and never looked back, except to occassionally take a peek at the competition.

The struggle itself toward the heights is enough to fill a man’s heart. One must imagine Sisyphus happy. – Albert Camus: “The Myth of Sisyphus”

The concept of vertical ascent is relatively simple - measure the change in altitude only when it is positive. On a loop course, the net altitude gain will always be zero, so we use vertical ascent to measure how hilly a course is. But numbers on paper are just that. 728 vertical feet (or vft.) over 5 miles doesn’t really mean much. It works out to an average grade of 2.8 percent, nothing spectacularly difficult. But when you are scrambling over rocks and roots, while your legs and lungs burn, as you drive yourself at an almost pitifully slow pace up a hill, it can seem like you are stuck in an M.C. Escher sketch, continuously climbing a staircase that never seems to end.

And so it was that on a cold and damp October morning, I found myself scrambling through muddy grass, over slick wooden bridges, and up (and up and up) the hills of the Mohonk Preserve in New Paltz, NY. The weather was a brisk 41 degrees Fahrenheit, a mark from which the mercury would not budge for the remainder of the day. Over five miles of carriage trails, I tried to mask the strain in my breathing from the one other runner shadowing me as we followed yellow arrows through the dimly lit forest. When we finally broke out into the field leading to transition after the opening loop of the American Zofingen Duathlon, I was only dimly aware of the fact that I would return to that loop for three more trips later that day. For the moment, I was concerned mostly with leaving transition in the lead. After a relatively slow transition, that involved putting on vest and windproof gloves, I headed out in first place. I rode down the dirt and gravel path that led out onto the bike course. It was wet on the roads, so I chose to forego wearing socks, fearing that they would get wet and make my feet colder, a decision that on a different day could have cost me the race.

The bike course immediately heads up hill, and, on this cold and rainy day, it literally took me into the clouds. The fog was thick around me, but not so thick that I couldn’t see a lone biker chasing behind me. I hammered the pedals, only vaguely regarding the wattage number on my SRM powermeterthat I would use to pace me through the rest of the day. On the first climb, I wanted to establish dominance. I wanted to make it clear that I would not, and could not, be caught. The power came easily. The pedals flew down effortlessly on the first climb of this 28 mile loop, a loop that I would ride three times, covering almost 3,000 vertical feet each time, making this perhaps the hilliest bike course of any ultra-distance race anywhere in the world. But for now, it was pedal down, pedal down, in a smooth steady rhythm. My legs were strong. They were fresh. And I felt my lead was growing. I would not be caught today and certainly not on this hill.

As I crested the hill, I shifted back down and relaxed my breathing, and began the long descent down from the Mohonk Golf Course. And this was where my lack of socks started to seem like a bad idea. My feet were cold and numb by the end of the winding descent on slick roads. But as I turned out onto the one flat section of the course, I slammed the pedals again, wanting to make sure that I was out of sight as quickly as possible. Break contact, and it’s easier to break someone’s will, especially on a day as punishing as the one before us. My legs still felt strong. I was riding too hard, and I knew I couldn’t hold that pace for 85 miles, but for now, it was what came when I asked my legs to work. On a wet day with leaves on the roads, it would be hard to attack the descents, so I knew I had attack the climbs. I knew that on the downhill sections, I would have to focus on bike handling, and that I wouldn’t be pedaling for a lot of that time, so I reasoned that I would recover then, so I could push a little harder when I was fighting gravity.

My coach warned me to cap my power output on the climbs and to not allow myself to dig too deep into my reserves. There are only so many “matches to burn” on a bike course. And on a course that went up as much as this one, it would be all too easy to burn them pulling myself up. But for now, the power came, and I rode it, up and up and up, climbing over 1,000 feet on the biggest climb of the course. My feet were cold, but other than that, I feltstrong, I was warm, and I was in the lead. As I finished up the first loop, I still felt strong. And I was at least a mile ahead, since there is a switchback loop right before the beginning/end of the loop where you c an see about a mile behind you, and I saw nothing but open roads and rain-soaked fields. With a clear lead, I resolved to more strictly obey my powermeter on the climbs. Riding up that first long climb, with two-thirds of the bike course left to go, I knew that before long the real struggle would be to stay above my minimum limit. But up and up I went, into the fog. The temperature had not budged, and by now, my feet were basically numb. As the day wore on, I became more and more ready to make a Faustian deal for a pair of dry socks.

About halfway through my second loop, I started to catch the back-of-the-pack riders from the short course duathlon (one loop run, one loop bike, one loop run), which was a pleasant distraction. I would lock one in my sights, and focusing on reeling them in, or “Hunting ‘Em Down” as I have adapted the sticker on my HED aerobars to mean. This is my mantra during triathlons, when I usually have some ground to make up coming out of the swim – breathe in, hunt ‘em down, breathe out. I watched the backs of the riders in front of me, and I watched my SRM screen - focusing on the numbers of each. My power was where I wanted it, now I just needed to keep it there.

But as I started the climb back towards the final loop, I knew that was going to be hard. My legs started to burn, and the lightness and snap that had been there on my first trip up the climb at the beginning of the loop was now long gone. I struggled to keep my cadence up, watching it, and my power with it, slip down. I was getting tired, but fortunately, no one was in sight. As I headed up the long climb, the sun peeked in and out, and the wind picked up, drying out the roads allowing me to carry a little more speed on the descents, and to relax and spin out the downhills more than earlier in the day, a welcome break for my legs.

Finally, after just under four and a half hours, I turned back into transition and made the final climb back on the dirt path to transition on weary legs. I racked my bike, and, finally, did something I’d been dreaming about all day – I put on dry, clean socks. I put on my trail running shoes, having been convinced on one loop in my now soaking wet cross-country shoes that I would want the extra grip of soles meant for trails. And I headed out on the run. And this is where the colossal stupidity of riding without socks really caught up with me – I couldn’t feel my feet. And as a result, I couldn’t move my feet. I was running totally flat footed. My feet might as well have been made of wood. Something needed to change fast, or there was no way I was going to be running 15 miles. Fortunately, the more I ran, the more the feeling came back to my feet, and after about two miles, I could flex my foot, and I was back running the hills, scrambling over the same roots I’d covered that morning. In the forest, my body was warming back up. Climbing up the hills, I started to sweat again, and I felt good, even as my legs burned much more than they had on the first trip, despite clearly going much slower than I had on fresh legs.

As I headed back towards transition, I overlapped the second place runner on a cross-over section of the trail. I was about 25 minutes ahead. But he looked strong, and I knew how tired I felt. I told myself that bike had punished everyone. There was no way he could run as fast as he had on fresh legs. But the real question was how much slower would he be? And how much slower was I? I tried to ignore that question, as I headed out on the second loop, with the feeling back in my feet, and the feeling of pain very, very strong in my legs. I told myself to just keep my feet moving; as long as I didn’t walk, he wouldn’t catch me, he couldn’t catch me. And near the end of the second loop, I overlapped the second place runner in the same spot as I had previously. I had lost no time. I knew if I could keep from walking and keep from passing out, which I very much felt like doing, I would win.

Just a short way into the third loop, I saw another runner up ahead. I tried to pick up the pace. I wanted to lap this runner. At the time, I didn’t know it, but that was the eventual third place finisher. But as he heard my footsteps, he picked up the pace, and my legs were just too tired to keep up. I fought to keep my focus sharp, telling myself to just keep my feet moving. I started to see some other runners out on their first loops, and I set to work passing them, focusing on the short distance between myself and them, rather than the seemingly endless distance to the finish line. As I passed the aid station for the last time, I grabbed a Red Bull, and, at that moment, I drank what tasted to me like the nectar of the gods. After a full day of Gatorade and gels, that soft drink was the best tasting thing I’d ever had. I had only two miles to go, and I had a boost, probably mental, from the caffeine. I felt like I flew (despite essentially shuffling) over the last part of the course. As I ran through the trees on the crest above transition people saw the flash of my red suit and began cheering.

Finally, I made it up the last grassy hill on the course, and then, barely, I climbed up the three stairs to the pavilion to break the makeshift finish-line. And just like that, it was over. Seven hours, twelve minutes, and thirty-one seconds after I had started, my day was done. I sat. My entire body screamed at me. My legs hurt. My back hurt. My feet hurt. But I was too tired to really even register it. I just sat. I ate the best tasting plate of pasta I’ve ever had. I drank glass after glass of orange juice. I changed into warm clothes. And I was as happy as I’ve ever been. “So,” I said to race director John McGovern, “are you gonna put this race on again next year?”