This story originally appeared in Mile High Sports MagazineRead the full digital edition.

How in the world does anybody actually finish last in anything? I mean, c’mon. Last? Of all the people attempting to do something, you’re the absolute worst? There is usually somebody in life better than you, but isn’t there always somebody in life worse than you?

Just look around your workplace – are you the worst person doing your job? No way! Go run a local 5K sometime. Even if you aren’t in great shape, there’s gotta be somebody worse. Those races are always filled with the guy 200 pounds overweight who decided it was a “victory” just to walk the entire distance in a little over two hours. You know that guy. He’s wrapping things up as everybody else has taken all the free bananas, bagels, Frisbees and other stuff from the endless supply of sponsor tents.

“Hey, we got all our free stuff. Okay, let’s get going. Oh look, that super-huge fat guy is crossing the finish line. Hey man, good for you! Looks like he’s the last one. Way to go!”

That’s the guy in last place, right? That’s not ever going to be you. I mean, that’s impossible. You would rather not enter an event than come in last. That certainly wasn’t going to be me. The state of Colorado is filled with a myriad of psycho-physical challenges, but finish last? Nah.

I was in great shape in the Spring of 2006. I was in maybe the best shape of my life. The previous summer I finished the Mt. Evans ascent. This is the race where you run up Mt. Evans road. Yep, you run up a 14.6-mile road to the top of a 14er. The event was in early June. In the final half hour of the race, a windy, slushy, icy, snow had been dumped – three inches! – along the course. I, along with all the other finishing competitors, had to walk up the final stages of the mountain – backwards – in order to finish. I did so. I didn’t finish first by a long shot, but I certainly didn’t finish last. In fact, I was actually in a van coming down the mountain picking up stragglers. I mean, these folks didn’t even finish at all. Later that fall, I would run the Chicago marathon in under four hours. I crushed more than half the field of 50,000 runners. In March, I would do the America’s Uphill event in Aspen where you throw on some snowshoes and run up Ajax Mountain. Again, I wasn’t close to the front of the pack, but there were many, many other racers that finished behind me. I was training for the Boston Marathon in which I would finish in 4:03, which was my best time out of the four times I completed Boston.

As I look back on all these things, now breathing hard as I walk up a flight of stairs, it seems impossible that I actually came in last in anything. But alas, I did. Dead last.

I’m not talking about last in my age group. I’m not talking about last in the men’s division. I’m talking last. Every man, woman and child that entered this particular event beat me. Every single person who paid an entry fee, got a bib, left the house early in the morning, ate oatmeal and showed up, beat me. Out of all the people that got free t-shirts, hats, gloves or whatever the giveaway items were, I was the person that got all that stuff and finished last. Despite being in the best shape of my life, I was that dude who was 200 pounds overweight, that everybody was waiting for at the finish line, applauding slowly – for me – as they were packing up all their belongings to go home because all the free stuff had been given away.

I finished last at the Imperial Challenge.

The Imperial Challenge is held on the final ski weekend of the year in April in Breckenridge, Colo. It has a long history of lung-burning conquests. This insane endeavor opens with a 6.3-mile uphill bike ride from the Breckenridge Rec Center, then continues with a 2,998-foot ascent from the Peak 8 base area at the Breck ski resort to the top of the Imperial Bowl, elevation 12,998 feet. From there, you have to figure out how to get down the double black diamond, ungroomed Imperial Bowl until you get to the friendly confines of the slushy spring skiing blue and green trails that take you to the finish line.

The most fit of the fit, those that have nicknames like “Iron Lung,” finish the race in around 100 minutes or so. For most folks, somewhere around two to two-and-a-half hours would be spectacular. There is a three-hour cutoff window at the top of the T-bar before you finish the final ascent. Just getting to that point is fantastic. Oh, and there’s a little trick, you can’t stash gear by the top of the mountain. Of course not! Whatever you go up with is what you have to come down with. The race organizers don’t really care how you get up or down as long you carry it top to bottom. I’m not exactly sure why they throw in the 6.3-mile uphill bike ride. It’s like saying, “You know, running up a mountain in snow isn’t quite hard enough. Hey, I got it! Let’s make everybody ride a bike – uphill. Yeah! Now it’s a race.” At least they let you stash your gear at the base of Peak 8 and not have to carry it with you on your bike. Although, I betcha there’s been a masochistic conversation or two about having everybody hump their gear even on the bike.

Who does this insane event? Well, it’s nuts like Breck’s Mark Beardsley, who wears duct-taped jeans and finishes in 95 minutes. It’s teenagers like 17-year old Kevin Soller, who was a high school senior and finished in 94 minutes. It’s Scott “The Human Lung” Yule, who at age 50 finished seventh overall. It’s wack jobs like Breck’s Mark Taylor, the only person to complete all 15 challenges, and Army Major Mike Hagen who said he could’ve finished better than third if he hadn’t done a 90-minute swim, a 90-minute bike ride and then skinned up to the summit of Peak 8 from the base of Peak 9 the day before the race!

There are adventure team pros. There are people in the Mountain Biking Hall of Fame. (Who knew that existed?) There were 246 folks that signed up this particular year and there had to be somebody who came in 246th.

That person – well, that person – was me.

***

Let’s back up a couple of years from 2006. I was working as a morning shock jock at KBPI in Denver. Money-wise I was doing okay, but I never turned down a chance to make, well, more money. They needed somebody from the station to host an event at Breckenridge. There were some awesome perks including a hotel room and free passes, plus I would get paid $300 bucks for a two-hour event. Sign me up!

I had no idea what they needed me to do. Hey, did it really matter? My family slept in, and from 8 to 10 a.m. I hung out at the transition area of the Imperial Challenge at the base of Peak 8. This was the final weekend of skiing at Breckenridge; Vail Resorts was just looking to spice things up a tad by promoting their final weekend. I guess having a Rock ‘n’ Roll DJ who would ask women to take their tops off for prizes was the ideal way to celebrate the end of the ski season.

When I arrived, I saw the endless collection of backpacks and a wide variety of ski gear littered all over the place. Strange. I was in full DJ mode, passing out bumper stickers and lip balm when all of a sudden folks started rolling up on mountain bikes. This is weird. You see, nobody told me that I was actually in the middle of a race.

“Where are these folks coming from?” I asked.

“Oh, they just biked up from the rec center.”

“The rec center back down the hill in Breckenridge?”

“Is there another rec center?”

For the next half hour or so, I saw some of the heartiest of folks in my life take thousand-dollar mountain bikes and throw them to the side like they were pieces of garbage. The racers would then put on either snowshoes or use skis with “skins” and start running up the mountain. Skins are a material you can put on a ski that will grip as you move uphill. The skis that you put skins on can vary from Nordic/cross-country gear to heavier skis called “Alpine Touring” setups. The advantage of the AT setup is that, while heavier than the Nordic gear, you have the flexibility to click the heel in when it’s time to go downhill and you have a much sturdier, more stable and faster ski. When you go downhill with Nordic gear, you are basically in a terrifying, nonstop free fall. The other option is to use small snowshoes and just carry a snowboard on your back. I found out all this info much later. At the time, I was just stunned that a race like this even existed.

Like a line of ants, I could see the competitors creep up Breckenridge. It was a small, dark curvy line that seemed to endlessly continue to the top of the mountain. I was incredulous, as I found out that these brave souls were doing something so extreme that I was filled with envy and respect. As the first finishers were dashing down the mountain and sliding home to victory to cheers and cowbells, I vowed that I would be doing this event the next year, not watching it.

I was lucky at this point in my life to be extremely motivated to push myself to my physical max. I had a young family that would indulge my weekend adventures. Simple 5K races were not enough. I had done more 10Ks and half-marathons than I could count. I had even pulled off a half-dozen marathons. I was scheduled to do a medium-sized, 14-mile run the weekend before I would attempt my third Boston Marathon, but those types of runs were always pretty boring. Hey, why not run up a mountain instead? I was an idiot from the get go.

First, I had absolutely nothing. I didn’t have a mountain bike. I didn’t have skins or AT skis. I didn’t have a clue. I just figured, what the heck, I’m in really good shape. How hard can this be? A month before the race, I decided to train a little bit. I got some snowshoes, threw my boots and skis in a pack and climbed up Loveland. I was stunned how hard this actually was to do. I had done other uphill adventures, but nothing where I had to carry so much crap on my back. Okay, this sucked. Adding insult to injury, a glass truck overturned on I-70 on my way home and I had to spend four hours in Silver Plume. Have you ever killed four hours in the small town just west of Georgetown? Let me tell you – it ain’t easy. I’m just saying, there were signs that this whole thing was a bad idea.

The snowshoes were out. The gear was just too heavy. Skins were in! The only problem is that I would have zero time to actually test them out. I went to an Alpine store in Golden where some transient hippie was putting away all the winter gear. He believed they still had some AT gear – well, you know – somewhere.

It was April and we had been enjoying a spate of incredible weather. Everybody was in t-shirts and shorts. The concept of skinning up a mountain was far from most people’s minds. This was Birkenstock and mountain bike weather. I’m sure there was a bluegrass festival this guy would’ve rather been attending instead of helping me find heavy-duty ski gear.

After rustling around awhile in a back room, the bearded hippie came out with the oddest contraption I had ever seen. The skis were wide and pretty heavy, much bigger than a cross-country ski. However, the ski boots were extremely light. He explained that the ski was really meant to go uphill with the skins so the boots didn’t have the heft of the normal downhill boot. You would lock in your toe and the heel could move up and down until you wanted to go downhill. When you got to that moment, all you had to do was lock down the back of the heel, “like this.” With a slight movement and subtle click, the heel of the boot quickly locked in.

“There you go. Now it’s a downhill ski… and oh,” he said, “these things are worth a couple thousand dollars, so, you know, don’t lose them.”

How the hell was I gonna lose them? They were going to propel me to glory!

I thanked the hippie, wished him the best in his goal to not wear a shirt all summer, and left the ski shop now armed with the implements of success.

A couple of days later, I picked up a mountain bike at a local shop in Breckenridge. This whole thing was becoming easier than I thought. I didn’t even care what the bike was. Hey, I only need it for six miles. Give me anything; I will have it back to you in a couple of hours. I really felt confident. My marathon training was going great. My new ski gear, which I had never really used, looked great. The piece of crap mountain bike looked, well, you know, good enough. I wasn’t trying to win this thing, I was just trying to figure out a more exciting way to train for Boston and check off another fun adventure from the list. Honestly, as impressed as I was when I had witnessed the Imperial the previous year, I just didn’t think it would be all that hard.

But don’t forget – I came in last.

***

The morning of the race, I left my pack with all the others at Peak 8. I had my bib and all my gear ready to go. It was a crisp but clear day and getting warmer by the second. Perfect. I got my rental bike good to go and I was ready for action.

Three… Two… One… Air horn… GO!

I took off like a shot! The first stretch of the bike ride was actually slightly downhill. Hey this is great! I pushed out with the lead pack. This ain’t so hard. Then about a half-mile in, we took our first turn uphill. I fell back a little bit, but not too bad. I had done about 40 spin classes that winter. I was fine. We hit our first switchback and the road got steeper. My breath got heavier. I was being passed by more people. Okay, you know, whatever. Then, in a stunning development, the switchbacks resembled something you would see in the Tour de France. What the hell? Why aren’t we just on a normal road like the one I rode down on in my car? Heavy, heavy, heavy. I was really struggling.

The mountain didn’t seem to stop. I kept visualizing what Tomas, my spin instructor, would say at this moment in a slight Swedish accent – “Out of the saddle! Now POOOSH! POOOSH! POOOSH! You can do it. Now, almost at the top of the hill, and POOOSH! And yes, yes, yes… Ahhh back in the saddle… and get some water.”

Of course, I was nowhere close to the top of the hill. I couldn’t reach my water bottle and in a humiliating moment I had to get off my bike and walk it up the hill. Of course, now I’m just getting destroyed as people are passing me left and right. It was a tough pill to swallow – Tomas would’ve been very disappointed. But, I wasn’t giving up. The entire ride wasn’t all uphill. There were significant stretches where you could fly down the road, but the uphill sections were brutal. Despite my struggles, I did notice there were people behind me.

Good. Not last.

In the transition area, I was probably in the bottom third of the competitors, but not too bad. There were air horns and cowbells and I noticed another shock jock from another station was handing out bumper stickers. I felt a huge resurgence of energy and pride. Sure the bike thing didn’t go great, but this was my wheelhouse – walking uphill and skiing down. I was in great shape and an expert skier. The bike crap was in my past! I had practiced with the gear in my hotel room the night before. The transition went smooth and I was off. I was fired up for the first 300 yards or so until it hit me: “Damn, walking uphill is actually harder than the stupid bike!”

OH MY GOD! This is freaking hard. The skins were working great, but the overall heaviness of the ski caught me by surprise. I thought because I was carrying such a light backpack – I only needed to carry some water and have room to put the skins in when I came down – that I would have an easier time than when I failed at Loveland a month prior. I was quickly out of breath because I was pushing too hard. I had to find some sort of rhythm. The key was to actually slow down and find a comfortable pace, which of course meant more people were going to pass me, which they did. Mentally, I just had to slow down. This was nothing like running a marathon. This was harder. I just decided to split the entire race into the towers that carried the ski lift. One tower at a time. Eventually, I fell into pace with another wretch like me. We silently agreed to pace each other switching the lead back and forth with a heaving grudge and a nod. It was happening, but boy was it slow. On the final ascent of the T-bar, very near the top, I realized it was actually too steep for my skins. I saw other folks having the same issue. The cutoff was looming. If I didn’t get to the top of the hill in the next 15 minutes, I wouldn’t be allowed to continue. In a bit of a desperate move, I took off the skis, put them on my shoulders, used my poles for balance and used some well-worn toeholds from other racers.

It took everything I had to get up the final 50 yards. It was five steps – rest – five steps – rest – five steps – rest – until finally, just under the wire, I made it to the ski patrol hut. But that wasn’t the finish. The race was to the top of the mountain, which was another 40-minute climb. The path was so rough that you couldn’t wear the skis at all. So, I slung them over my shoulders and began the final push. I was thrilled that I had hit the time cutoff and energized by what I knew – despite its altitude –was a relatively easy ascent.

Well, it used to be easy, back when I was a normal skier at Breck and I just schlepped up the ridge after taking lifts all the way to this point.

My legs were heavy and breath was shallow. Just when I thought it was over, the nightmare was beginning again. Somehow I trudged to the top, my boots caked with snow. The day was decent, but it’s always gonna be cold and snowy at the top of Breck. With a deep sigh of relief, I finally hit the summit. There were maybe seven or so people behind me.

I gasped for air as a race official checked me in. It was over! All I had to do was ski down! I don’t mean to brag, but I can ski down basically anything. Whew! As I was silently rejoicing in my head, I realized that I couldn’t get the boot to click into the back heel of the binding.

What the F$%$!!!!???  

It had worked great the night before… in the hotel… which was… well… warm and dry. For 15 minutes I struggled getting that damn binding to work. My fingers were brittle. My head was swimming. I was absolutely starting to panic. The seven folks behind me were quickly catching up. They were getting to the top and getting their gear on in record speed. I was stuck in the mud while smack dab in the frozen tundra. I lost my head and just decided to jury rig both bindings with the strap provided – there are no brakes on these skis like traditional downhill skis. I thought if I could tie myself in, I would be okay. I was officially insane.

“Okay,” I said, knowing there were now only two people behind me, “here I go,” sliding off into a double black diamond run that would be tricky in even the best conditions. I slid down to my right in a precarious manner. Uhhhhhhh. Then I made a turn to my left. Uhhhhhhh. This doesn’t feel good. The speed increased and there was no way to slow down. AHHHHHHHHHH damn! This isn’t going to end well. I took another sharp turn at a precarious angle to my right and it was if I was shot off a rocket. My heels fell out the back; the straps that were being used like an Icelandic binding from the turn of the century whipped off my legs.

I fell on my back as my left ski shot off my foot, raced down the hill and disappeared over a cliff. My right ski also came loose and went in the complete opposite direction, tumbling down the hill before landing straight up and down in the snow 800 feet below me. At least, I could see that ski. My other ski was nowhere to be found – no clue where it went. Gone.

Now what? I scooted down on my butt towards the one ski I could locate.

“Hey, are you okay?”

This came from one of the two people I was still ahead of in the race.

“Yeah. Thanks,” I said.

With a nod, he took off and I was officially in second-to-last place. I picked up my one ski and realized that my only hope in finishing the race was to walk down the mountain I had just walked up. Well, at least walking down was kind of easy. Usually the descent down the mountain would take five minutes or so. The walk back down took me another 50 minutes.

Along the way down, the final racer passed me. I got another, “Hey, are you okay?”

I was. Go ahead. I know I will be in last place.

Then, race officials on snowmobiles approached me. They weren’t really concerned if I was okay, they just wanted to finish the damn race. I refused to take a ride down the hill, knowing that would disqualify me. They were pissed. I didn’t care. I expected a hero’s welcome at the finish. I would be last, but look at the effort!

Nope.

The clock was still ticking, but the entire finish line was packed up. There was one ticked-off dude sitting on a chair with a clock. As I finished to zero applause, the race official sarcastically clapped once, said “GREAT” very sarcastically, and then turned off the race clock. I had done it. I had finished the race. I had come in last. It wasn’t glorious, but I got it done.

The next day, I called the ski patrol who said they had found my other ski. Thank God, because I didn’t have two grand for the hippie. The next year, I did the race again. This time I used snowshoes, carried my wife’s lighter skis and boots, which I kept dry in a bag so there was no snow when I clicked them in easily at the top of the mountain. I easily beat 40 or so people, despite horrible conditions.

I smiled at the top of the mountain and that has been my profile picture on Twitter for the past 10 years or so. It was a smile that told everybody, I was once a fool and I learned from my mistakes.

Many people have asked why I have that picture on Twitter and I’ve never really explained the story. Until now.

I was proud… to finish last.