“We can’t win at home. We can’t win on the road. As general manager, I just can’t figure out where else to play.”

Pat Williams

In the grand carnival that is American sports, my allegiance was a comedy sketch: I cheered for the Dallas Cowboys, the NFL’s equivalent of the high school quarterback everyone adores, and the Houston Oilers, the scrappy drama club hero with a penchant for tragic endings. This was Texas, where football loyalties run deeper than family ties, and here I was, straddling the line like a tightrope walker in a gusty wind.

The Oilers were a team that specialized in heartbreak, crafting losses from the jaws of victory with the skill of a master sculptor chiseling away at marble. Remember the playoff game against the Buffalo Bills? That wasn’t just a defeat; it was a Shakespearean tragedy, a masterclass in how to lose when all signs pointed to triumph. It was like watching your ice cream fall off the cone and onto the pavement on a hot summer day—painful, unnecessary, and entirely avoidable.

Then there was the time we faced John Elway and the Denver Broncos. If there were ever a manual on how to snatch defeat from the clutches of victory, that game would be Exhibit A. Each of these moments was a lesson in humility, a reminder that hope is the most treacherous of emotions, especially when you’re an Oilers fan.

The turning point came during a spirited debate with my friend Jerry Ruiz. Jerry, a Cowboys loyalist, couldn’t fathom my split affections. To him, it was like cheering for both Romeo and Paris to win Juliet’s heart. In a moment of adolescent fervor, I threw my full support behind the Oilers, forsaking the Cowboys in a move that was part teenage rebellion, part loyalty to the underdog.

This decision wasn’t just about sports; it was a rite of passage, a declaration of independence. I became “the Oilers guy,” a title I wore like a badge of honor, even as it often felt more like a scarlet letter.

As the years rolled on, the fervor of youth gave way to the wisdom of age. The Cowboys, with their glitz and glamour, slowly won back a place in my heart, not as the sole occupant, but as a cherished companion to the memories of the Oilers.

What I learned from those years of undying loyalty to a team known more for its losses than its wins was the beauty of resilience. The Oilers taught me that there’s a peculiar joy in rooting for the underdog, a kind of mirth in the madness. Life, much like football, is unpredictable and often ridiculous, but it’s the laughter and the shared moments of disbelief that make it all worthwhile.

In retrospect, being an Oilers fan was like being part of a special club where the admission fee was a broken heart and the membership came with endless tales of what could have been. It was a lesson in finding humor in the face of disappointment and a reminder that sometimes, the most memorable stories come not from the victories, but from the spectacular collapses. And if you can’t laugh at that, then maybe you’re taking the game—and life—a little too seriously.

Stephen Boudreau serves as VP of Product + Content Marketing at Virtuous Software. For over two decades, he has helped nonprofits leverage the digital space to grow their impact. To that end, Stephen co-founded RaiseDonors, a platform that provides nonprofits with technology and experiences that remove barriers to successful online fundraising. He is an avid (but aging) soccer player, audiobook enthusiast, and the heavily-disputed UNO champion of his household.

Copyright ©2024 Stephen Boudreau.