A High Sierra Regatta We Won’t Forget

The only thing better than the sound of new sails is the sound of your friends cheering from the shoreline. That’s what I wanted this year’s High Sierra Regatta to be about. But like most good sailing stories, things didn’t quite go according to plan.

It was a beautiful morning — the kind where the sun stretches lazily across camp, slowly peeling back the chill that settled in overnight. The lake lay still, with rowers gliding like whispers across its glassy surface as the low haze began to lift. Spirits were high. We had the Lusty crew from Mexico and the Sitkas by our side, cheering us on as we prepared to race alongside Mitch and Quincey, who now officially owned Little Blue Boat (formerly Sniper One). It felt as if things were shaping up to be a great weekend.

It had been over a year since Geronimo had danced with the wind. We were extra-excited to hoist our brand-new sails from Precision Sails, convinced they’d give us that extra edge. If confidence could win regattas, we were already on the podium just by association.

Saturday: After breakfast, Chris and I rigged Geronimo and made our way out to the start line, tacking alongside our fleet and weaving between the other classes that dotted the lake like confetti. That familiar hum of adrenaline settled into my stomach as I managed the sheets under Chris’s calm (but focused) commands. At the sound of the gun, we were off third over the line, our new sails filling beautifully as we charged up the course.

We finished sixth, but it was a tight race — one of those finishes where you’re still grinning, knowing you fought for every inch. Spirits were high. Then came the second start. We were forced to tack early to avoid a couple of rogue kayakers who had paddled right into the starting area, throwing off our timing and positioning. Still, we clawed our way back, picking off boats one by one. It was shaping up to be a decent recovery … until we rounded the second downwind mark.

That’s when we collided with Red Eye.

Red Eye is the legendary boat owned by Chris’s Uncle Scooter — the godfather of the Victory 21 fleet, and quite literally the reason we’re all here. For the first time in over two decades, Scooter wasn’t at the helm. Instead, he’d passed the tiller to his fraternity brother and longtime crew, Chuck Phillips, known to us as Uncle Chuck.

Red Eye is notorious for always landing on the podium. Their crew never reveals their secrets — black magic, we joke — and we’ve spent years trying to beat them. We never imagined it would happen like this.

“You see Red Eye coming up?” I asked from the bow, bracing to douse the whisker pole. We were on a downwind port tack about to round the mark, while Red Eye was on an upwind starboard tack.

“Yeah, I see them,” Chris replied — right as Chuck’s booming “STARBOARD!” cut through the wind. In a blink, our boom was against their cap shroud, pulling them from their course and breaking their mast in half.

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