Alex Boylan (TAR 2 Winner) Speaks about his experience

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The Day I...Won The Amazing Race

Alex Boylan with Ryan Bernstein


If it's possible to have a defining moment in one's life without being defined by that moment, winning The Amazing Race was it. The 28 days I spent racing around the world with my high school buddy Chris, competing for $1 million against 11 other teams, truly was an experience of a lifetime.

My race, The Amazing Race II, arguably was one of the most intense, action packed, adrenaline pumping finishes ever aired on reality television. It was everything you could hope for in a race. When you talk about bottling an emotion, 28 days of fierce competition covering 55,000 miles and five continents, The Amazing Race is the perfect recipe for thrills. It's little wonder the show has gone on to win four Emmys for CBS and is now currently in the midst of its tenth race.

My involvement in the race all came about by chance. One hot summer night, I was relaxing on my deck, messing around on my computer when this pop-up appeared on my screen: "Race around the world for a $1 million." At the time, Survivor was the only reality show out there. The notion of traveling around the world using clues to propel your team to the next location while competing against others to win money was mind blowing.

The biggest difference between our race and the races now is like comparing the purity of college sports versus the pros. When I raced, no one new what to expect. Everything was fresh and exciting. All we had for reference was Survivor, which was pretty intense and raw. You did it for the thrill of victory. You never knew what you'd get out of the racers or in the case of Survivor, the survivalists. Now, reality "players" are cast more specifically. They're personalities instead of people. For them, it's about money and fame. The "players" know how to get camera time – what to do or what to say. For me, after the first 10 minutes of the first leg I forgot there was a camera crew. There were times when Chris and I were so focused and locked in, that we barely uttered a word for hours.
More than 50,000 miles begins with single footsteps.

I had just quit my job in corporate America and my buddy Chris was just finishing up school. We hated what we were doing, so to pass the time until we figured out our lives, we worked as bouncers at local bars in our hometown of Boston. The deadline for audition tapes was in a day and half, so I called up Chris that night, and we had another friend put us on tape. The next morning we sent it off via FedEx and then forgot about it.

Earlier that summer, Chris and I received two free tickets to Europe. The plan was to travel for a few months without any direction or plan and then come back to the states ready to make a go at our future. Before our sojourn began, we decided to spend a few days with my parents - already in the Swiss Alps staying with friends.

The day before Chris and I were scheduled to disappear off the grid for several months, the phone rang. Normally this wouldn't be a particularly strange event. However, my parents' friends said that the phone hadn't rung since they'd been there going on three weeks. It was Chris' mom. Apparently CBS had been trying to track us down for the past few days and was ready to give up on us. They wanted us in New York City for the next round of interviews.

In New York, the producers told us that our interview tape was the worst they'd ever seen, however they loved the way we interacted. I said, "That only comes from knowing someone your entire life as Chris and I had." We underwent several more rounds of interviews until the producers finally selected their 11 teams that would push their bodies and minds to the limits all, with hopes of a million dollars in the near future.

As a 24 year-old, only two years removed from the NCAA college soccer sweet 16, I approached The Amazing Race the only way I knew how – as a game. Albeit the most intense game I'd ever been involved in. For Chris and me this was Darwinism at its best. For us, it wasn't about money or celebrity. It was about competition and beating everyone pitted against us.

All we knew was the race would start somewhere in Nevada. Beyond that, we had no idea where we'd be going, how long we'd be gone and when we'd be coming back. A week prior to the start of the race, the producers flew the 11 teams out to Vegas in order to go over the rules of the race and make sure we knew everything we needed to know. The one rule however was, no intra-team interaction. They specifically wanted all relationships to develop on camera.

It was strange not being able to size up our opponents. I didn't have any anxiety, but like any good athlete, I wanted some form of scouting report on whom I was about to go up against. As Chris and I lay in our beds that week in Vegas, we talked about winning the race. We didn't develop any strategies; we just visualized crossing the finish line first.
All I had to go on was my own experiences in terms of how we would fare against the other teams. I'd lived in Brazil, Caribbean and Germany. I looked around whenever all the teams were together and said, "Is there anybody here who's traveled like I have, with as little as I have, by themselves?" Then I looked at Chris who is way smarter than I am, and I just knew – we were going to win.

The one strategy Chris and I did develop was forming an alliance with one of the other teams. We targeted Wil and Tara, the eventual second place finishers. We did this because Wil and Tara had extensive knowledge of Asia – the one place I'd never traveled to. Collectively we decided to aid each other's cause until we'd each advance into the final three. It turns out the alliance benefited both teams.

The other team in the final three, Blake and Paige, never seemed to pose a threat to Chris and me. From 11 teams down to the final three, Wil and Tara were our greatest competition and eventual arch nemesis.

When you're in the race you don't think about the big picture. You can't. You have no idea where or when it's going to end. You don't know what day of the week it is, and you're operating on very little sleep. All you can really focus on is the task and moment at hand. We could be friends before the race, and we could be friends after, but during the battle, it was all about victory. So if I hurt your feelings, too bad. It's a sport, and I'm here to win. That's I think what separated Chris and I from everyone else. We didn't let our emotions get in the way.

A perfect example was when Wil and Tara had lost their clue before heading to Alaska, and unbeknownst to us, the last day of the race. They approached Chris and me and asked if we could tell them where they needed to be and what they needed to do. As nice as I could, I reminded them of our agreement that the alliance ended when we made the final three. Wil persisted to the point that I had to shut him down with a harsh "no" and walked away. He was furious and more determined than ever to beat us. I kind of got the feeling that Wil didn't even care if he finished second, as long as he finished ahead of the two of us.

Wil and Tara managed to make it to Alaska by tailing us to our plane and eventually telling their pilot to "follow that plane." When I learned of what they had done, I was overcome with a very quick moment of anger. I quickly calmed down; there was no time to lose it at this juncture. Little did I know, we would return the favor, which eventually won Chris and me the race.
Chris and Alex seconds from winning and $1 million.

The day of the last leg, we woke up somewhere in Alaska after spending the night in an igloo. In Alaska during January, the cold air crushes your lungs and freezes any part of your body that's exposed. By then we had traveled more than 50,000 miles. I wanted the race to end.

We hadn't slept for three days; we hadn't eaten very much. My mind was losing perspective; my body was running on fumes. I didn't know how much more of this I could take. If there had been a part of my body or mind that could stretch, it was snapped.
We set out in the bitter cold for our final challenges – a husky ski pull. This challenge never aired. It was too intense, and the producers felt it wouldn't go over well with the viewers. The idea was that two husky dogs would pull a team member on skis across frozen earth.
Chris is a big guy – 6'3", 220 pounds – these dogs worked. At one point, he's carrying the dogs trying to cross the finish line. I'm an animal lover, but I'm beating my dogs to go faster. All I can think of is that the finish line could have been at the end of this leg, and I'd be damned if I was going to let some dogs keep me from nirvana.

Next, we all got into Snow Cats and set out across a frozen lakebed in search of our next clue. The sweat I'd built up from the ski pull was starting to freeze on my face and neck sending an icy chill deep inside my bones. My face was raw and burnt from the wind and sun tearing at my skin. The only thing that kept me from breaking down and collapsing in a heap on the snow was the fierce heat of competition.

From the Snow Cats we hopped into 4 X 4's and drove 50 miles to the middle of nowhere, which is all relative in Alaska. We had to bust through a block of ice to get our next set of instructions. Chris immediately hopped out of the car and shattered the block in a few blows.

The clue lifted my spirits. We were headed back to San Francisco. I swelled with emotion, finally sensing some closure to the 28 days of madness we had endured. The goal was within reach. Now we just had to get to the city by the bay.

We came to a literal and figurative fork in the road. Do we drive to Anchorage for our flight back to San Francisco or do we go to Fairbanks? I had no idea. Which was closer? I looked at the map and immediately guessed Fairbanks International Airport. Several hours into the drive, I began to worry. I made a mistake that surely cost us the chance of prevailing as champions of race two. I was barely hanging on. How could I have been so stupid? My thoughts were distorted.

The entire ride, Chris and I barely uttered two words. When we arrived at Fairbanks International Airport, we raced up to the counter and I asked the ticket agent the only thing that was on my mind – "Is there any way another flight from anywhere in Alaska could beat us back to the States?" When she assured me there was none, all the tension left my body like a deflated balloon. Only then did I realize there had been a throbbing behind my eyeballs for the past two hours.

Feeling at ease that my decision hadn't cost us the race, Chris and I went to grab something to eat. When we returned, the ticket lady was ashen-faced. She had made a mistake. There was a flight leaving Anchorage for Oakland sooner than she thought. We had less than five minutes to get on a plane that was sitting on the tarmac that would take us to Anchorage, which would get us on that plane to Oakland. We made it with a minute to spare.

The airports were the great equalizer, so it actually became important where you sat on the plane. If you were in the back, you lost valuable minutes from somebody sitting in the front. When I walked up to the ticket counter in Anchorage, I was floored when the ticket agent gave Chris and me first class seats. Apparently, the other two teams had been complete assholes so she wanted help us out.

As soon as the plane landed, Chris and I were two rockets blasting through the airport. I'd like to take this opportunity to apologize to all the women and children we bowled over trying to get the first cab. We were headed to Atkinson-Esher house, the oldest building in San Francisco, with the possibility to end the race and win the million dollars. Nothing was going to stand in our way.

We arrived at Atkinson-Esher house first and grabbed our next clue. I felt no pain. No fatigue. I was focused and locked in like a laser beam. The next clue set us off to the Municipal Pier. As we were pulling away, relief washed over my body as I saw Wil and Tara pulling up.

The clue said we could not take any public transportation to the piers, so Chris and I took off running. This was our strength over the other competitors – our athleticism. When we got to the piers, my heart sank. There were a hundred piers and all of them were municipal. The Fairbanks incident shook my confidence a bit, and I didn't want to make another costly mistake. It was going to come down to who guessed right.

We started smack dap in the middle. We discovered after a few piers that the actual Municipal Pier was the last one on the end in the direction we were heading. Bingo!
About 100 yards out, we took the biggest blow you could possibly imagine – Wil and Tara had made it there ahead of us and were leaving the pier with their clue. They were going to gain at least five minutes on us. At that stage, that's an eternity.

As we made it to the box – I knew it was the last clue because it said go to East Fort Baker and cross the finish line – my stomach twisted in knots. For the first time since this whole experience began, I told myself that second place was good enough. That's all I could do to keep going.

When we pulled away from the pier – our cabbie had no idea where East Fort Baker was – the higher powers intervened for the last time. Wil and Tara had not been able to get a cab and were just hopping in as we pulled around the corner. That competitive fire roared back to life as I told our driver to "follow that cab." All we had to do was follow Wil and Tara. It was a scene straight out of the movies. There was new life.
Chris and Alex in Rio.

CONTINUATION>>>>>>>>

Just a few days back, I said to Chris that if we were close at the end, and it came down to a foot race, we'd finish as champions. Well here we were, neck and neck with our opponent. Wil knew we were following them and tried to throw us off the trail. He stopped his cab and got out trying to dupe us into believing we had arrived at East Fort Baker. We didn't take the bait.

Wil made a critical mistake. By getting out of his cab and running several hundred yards hoping we'd follow, it gave me an opportunity to ask people where East Fort Baker was. A tractor-trailer driver on the side of the road told us it was the first exit off the Bay Bridge. Armed with that we were off.

Just as we were about to exit, Wil and Tara's cab zoomed in front of us. They appeared from out of nowhere. To add to the frustration, a mini-van got between our cab and theirs. We were trapped on a one-lane road behind the slowest driver in America. Wil and Tara started to pull away. That sinking feeling started to settle in again as I had no idea how much distance would need to be covered once we got out.

We came around the bend and saw an empty cab. It started to dawn on me that we could actually be fighting for third place. We hadn't seen Blake and Paige for a while, and they could be sitting at the finish line waiting for us. We jumped out of the cab without paying and tore off along a path.

Adrenaline coursing through my body pounded in my ears. My lungs were screaming from all the running. Fatigue was finally settling into my legs as my muscles burned. All that went away when we came around another bend and saw a hill in front of us. At the base of the hill were Wil and Tara.

Chris and I looked at each other; we knew we had it. We only had to make up 300 yards. There was no way Tara was going to beat us up that hill. This was it. On the other side of that hill was the finish line.

Wil was first to crest the hill followed a few steps behind by me. The next person coming over that hill would determine which team would end this crazy journey as the winners. All the other teams were there cheering, and when Chris appeared ahead of Tara, they erupted.

As I collapsed on the mat, Chris soon after, I knew my life would be different. Right then and there, I knew this would a defining moment in my life. It's amazing the difference between finishing number one and number two.

We were these two hurricanes blowing threw the world; eyes wide-open thinking nothing could stop us. Winning The Amazing Race has opened some doors for me, but it was just a short time later that I was sweeping floors in a production company in Jacksonville. My legacy will not be Alex Boylan, winner of The Amazing Race. It will be Alex Boylan creator of his own destiny.

what a long story.. but it was fun reading it..