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On March 18, 2005, the Syracuse Orange suffered what has gone down as one of the biggest upsets in the last 20 years of the NCAA Tournament. That’s the night that Jim Boeheim’s club fell to the No. 13-seeded Vermont Catamounts, 60-57, in overtime. It’s a loss that most Syracuse fans want to forget about, which unfortunately isn’t going to be possible this year considering that articles are already starting to come out reflecting on that terrible, horrible, no good game for the Orange. For most fans of the Orange, it’s one of the worst losses in program history. For me, it’s something different. It’s a loss that I can only describe as bittersweet.

I’m a lifelong, die hard Syracuse University fan. I was raised on Orange basketball thanks to my dad, who grew up in Marcellus and was a devout fan of the Orangemen. But I was also born and raised in Vermont, and while I scoffed when a guidance counselor told me that applying to Syracuse was all well and good but I should probably look at UVM as another option (note: I never applied to UVM – the only school other than Syracuse I applied to was James Madison, in Virginia), over the years the Catamounts have become a team that I root for year in, and year out. It certainly hasn’t hurt that I’ve played with or against several players who have suited up for UVM.

One of those players was a kid named Tony Orciari, a former America East Player of the Year who was two years ahead of me, and I distinctly remember that when I was in fourth grade, the first time I ever tried to dribble the ball in an organized game, Tony came along and stole it from me. He went on to co-captain one of the best high school teams in Vermont state history alongside my brother. Another of those players was Taylor Coppenrath, and therein lies the entire reason for that 2005 first round defeat leaving me feeling more conflicted about a Syracuse basketball loss than any other in history.

I hated seeing Syracuse lose. Absolutely hated it. I was actually pretty happy to see Hakim Warrick, Gerry McNamara, and the rest of the Orange draw UVM in the first round, because I knew that SU held such a distinct advantage athletically that there was simply no way that Taylor and his compatriots in green could keep up. I fully expected a 25 point victory, assuming that Syracuse chose to dictate the tempo and run the Catamounts off the floor.

Unfortunately, that’s not what happened. Rather than pushing the pace and using the serious size and speed advantage at the team’s disposal, Syracuse allowed the Cats to dictate the tempo, and UVM started grinding it out with long possessions, turning the game into a battle of halfcourt offenses. For all Jim Boeheim’s greatness as a coach, I honestly don’t recall the last time the Orange were a truly superior team when it comes to halfcourt offense. And the fact that the Orange refused to exert their will, push the pace, and just run UVM off the court continues to astound and baffle me to this day.

But I still can’t stay completely upset about the loss, because like I said, I knew the star player for the Catamounts. I first came to know Taylor when I was about 12, and he was about 11. He was a year behind me, and we played with and against each other in the local AAU circuit in Vermont. Eventually, we wound up at the same high school, where he became my teammate my senior year. And yes, that does mean that Taylor didn’t make varsity until his junior year of high school. I won’t even begin to get into that, because it opens up a Pandora’s box of idiocy with regard to the sports politics at St. Johnsbury Academy in little St. Johnsbury, Vermont. Let’s just put it this way: when UVM coach Tom Brennan came calling about Taylor Coppenrath, our coach – a former UVM star himself – basically told Brennan he was wasting his time.

Clearly, our former high school coach was dead wrong, and Tom Brennan was a very wise man to ignore the pompous blowhard and go with what his own eyes were telling him. After all, I remember one home game my senior year against a rival that featured a kid named Matt Sheftic, a bruising 6-foot-8, 250 pound senior who had already committed to play for UVM, and who was expected to dominate us. Tom Brennan was in attendance for that game, and for a high school basketball game in Vermont, I remember the crowd being comically large, spilling out the doors of the gym. Everyone wanted to see what Matt Sheftic would do to us, and how thoroughly he would dominate Taylor.

Instead, the opposite happened. Taylor absolutely destroyed his future teammate, running circles around him up and down the floor. I honestly can’t remember if we won or lost that game (I believe we still lost, but Taylor completely outplayed his counterpart) but that’s beside the point. Taylor was also our soccer team’s goalkeeper, meaning that his quickness, hands, and anticipation were vastly underrated. He wasn’t the fleetest footed kid in the gym, but he was always a much better athlete than he was ever given credit for.

I admit, when I first met Taylor and even into his freshman and sophomore years of high school, I would have called you crazy if you’d told me he would wind up being a 3-time America East Player of the Year. I’ve always been happy to have been proven wrong. I’m thrilled that he’s been able to continue his playing career for all of these years in Europe, too, earning a good living playing professionally in places like Greece, Italy, and Spain.

And that’s why I’ve never been able to get completely bitter over that damned 2005 loss to UVM in Worcester. I hate that Syracuse lost. It drives me insane that Hakim Warrick’s college career ended on that note. But I still just can’t get completely mad about the loss, simply because I had a personal connection to the other side of the matchup. I never met Hakim Warrick while I was at Syracuse. The closest I ever came was simply remembering seeing him on his recruiting visit, walking around the Dome during a game alongside Damone Brown, looking like a 6-foot-8 preteen.

But I’ve known Taylor Coppenrath for more than half of my life at this point. So while I was disappointed in the way things played out for Syracuse, I couldn’t help but be at least a little bit thrilled for the guy who I still remember as a kind of pudgy, not particularly skilled 11 or 12 year old, who made an astonishing transformation into a legitimate NCAA Division I basketball player between the time I met him, and the time he became a redshirt freshman at UVM.

On the other hand, I never knew TJ Sorrentine. That’s why I’m comfortable, to this day, saying: screw TJ Sorrentine.

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Jeff is a 2003 graduate of Syracuse University, and has been published on various websites including Cracked.com, Spike.com, TheSportster.com, Gunaxin.com, and TopTenz.net, among others. His work was featured in the New York Times bestselling book You Might Be a Zombie and Other Bad News. He's got a wife, and a toddler he's brainwashing to love Syracuse. Jeff's a pretty great guy, overall, and would never steal your car. Follow him on Twitter: @jekelish