I’d never coached before. But somehow, during my second year of teaching high school in Brownsville, Texas, I was recruited to lead the boys’ junior-varsity basketball squad. As a former benchwarmer, I dove for the clipboard like a player scrambling for a loose ball.
That pre-season, I whistled the team through drills and scrimmages, determined for us not only to be great—but to be legendary. Our home court was two miles from the U.S.-Mexico border, and many of my players crossed the international bridge each morning and night. They spent their summers on farms, not at skills camps. So imagine how incredible it’d be if we annihilated the more well-heeled teams. We’d become borderland heroes, I was sure.
We lost our opener in the final minute. We’d turn a corner soon, I told myself. But the corner never came. For three months, we rode a bus up and down the border, enduring one brutal defeat after the next. Our critical weakness: the full-court press.
Opposing coaches, in an act of mercy, usually let up whenever they realized that my team couldn’t advance the ball past half court. But one refused to yield. He pressed with his starters, then with his B squad. When I gestured for grace, he pressed with his scrubs. When I called a time-out before half, my team captain was nearly in tears.
“Take me out, coach,” he pleaded. “Please.”
I tried my damnedest to be a good role model, but I was frustrated at my players, for being pitiful (we were supposed to be heroes!), and at myself, for being a miserable coach. The squad’s faith in me evaporated. They stopped inviting their girlfriends to games; I stopped inviting mine.
Near the end of the season, we traveled to a dusty border town to face a shorthanded team. To my surprise, we quickly pulled ahead, having found the only team in Texas more god-awful than we were. But if I could replay any game that season, I’d choose that one—our sole victory.
After months of blowouts, it was my chance to show mercy like other coaches had shown me, to be a good sport, to win right. But I wanted to demolish the other team, to prove that I wasn’t an utter failure. So, when the other coach signaled for me to let up, I pressed on, pretending I didn’t see him.
Sometimes a win can be a loss, too.
This essay is part of our Art of the Fail series.