The Wager
Two regulars bet a hundred dollars on a stranger's body. Only one of them did the math on what that meant.
Aspen Valley News · First Tracks
Order of play — read top to bottom
- 01CH·4The Settlementthe bar, after
- 02CH·1Last Callthe bet
- 03CH·3The LeanHal's hand
- 04CH·2The BellsDewey's voice
- 05CH·5The Billwho pays
The chapters are out of order on purpose. So was the bet. You get the stakes when they got them — last.
The Settlement
the bar, after
They settle up at 4:40, high-top at the Rendezvous, a folded hundred sitting between two beers like something neither one wants to pick up.
Hal slides it across. Dewey leaves it there.
"He finished."
"I know he finished. I'm trying to figure out which one of us almost got him killed doing it."
We'll get back to the bar. First the bet. You get the bet last.
Last Call
the bet
Nobody wins the Aspen Gran Fondo. It says so on the waiver. Twice. Right under the part about serious injury or death, which everybody signs without reading because it's printed next to a little cartoon of a smiling cyclist.
A hundred and three miles. Every mean climb the valley owns. Descents where the guardrail is more of an opinion than a guarantee. A beer tent at the bottom for whoever's still upright to reach it.
So two guys who post up at the same bar every June found a way to make it interesting. You can't bet on who wins. So they bet on one rider. A local. Showed up on a frame a size too big, ran his mouth at the start line about doing the full 103, and looked just green enough that you couldn't tell if it was confidence or a cry for help.
Dewey said he'd finish. Hal said they'd be peeling him off the descent by lunch. Hundred bucks. They shook on a stranger's odds the way you'd shake on a coin flip, and that should've told them both that something had gone a little crooked in them.
Neither said the other part out loud. Neither one planned on leaving it up to the mountain.
The Lean
Hal's hand
Mile seventy. The dirt above the Monastery, where the air thins out and starts asking you questions you don't have the breath to answer. Riders get wobbly up here. The eyes go flat. A guy can be sitting straight up and already gone, and the rider was starting to get that look, the one that shows up right before somebody forgets which lever is the brake.

This is where Hal figured he'd crack. So this is where Hal gave him a push toward cracking.
Hal works the course. Nobody questions a guy in a marshal's vest. He found his rider cooked at the bailout, gray, hands shaking on the bars, and got real soft about it. Nobody'd think less of you. The 62 still counts as a finish. Go on home before this turns into something.
He was lying about the kindness and telling the truth about the danger, which is the worst kind of lie there is, because it's half true. The next stretch was the long descent. That drop, on a rider in that shape, was a coin flip with a hundred dollars and a collarbone riding on it. Hal knew it. Hal leaned anyway.
The Bells
Dewey's voice
Back up. Before Hal talked, Dewey spent the whole morning holding the same door wide open, and not once did he stop to ask if the guy walking through it should be.
Dewey works the aid station up at the Bells. A man with a cold bottle and the right words can do a lot of good there, and a lot of damage, and it's the same voice doing both. He didn't touch the bike. He pressed a bottle into the rider's hand and told him he had more left in the tank than the whole carbon parade wheezing past him. Told him the ones who bail spend all winter wishing they hadn't.
Then he put his thumb right on the soft part of the guy's belief and pressed, and sent a half-cooked rider climbing toward the thin air on the strength of a compliment.
He had a hundred on it. He'd have done it for free. That's the part eating him now.
The Bill
who pays
The rider didn't crack. He stood at that bailout with Hal in one ear and Dewey in the other, and Dewey won. He clipped back in and rode away from the open door, straight at the descent two men had bet his body on.
He took it hot. Too deep into the first switchback, back wheel skating on the loose stuff right at the edge, and for half a second the whole bet hung out over the drop with him. Then the tire bit. Pure luck dressed up as skill. He never knew how close it came. The two guys who sent him there knew exactly.
He finished. The whole 103. Rolled into the tent caked in dirt, cramping, grinning, alive, and the whole place turned toward the one guy who actually did the thing.
Hal
You win.
Dewey
I didn't win because he was strong. I won because of what I said at the Bells.
Dewey
Buy the kid his first round. Leave both our names off it. He thinks he did it by himself. Let him keep thinking that.
Hal
He did do it by himself.
Dewey
No. But he gets to believe he did. That's the only clean thing either of us touched all day.
Across the tent the rider walks in, still wearing his number, still wearing the dirt, with no idea two guys at a bar spent the day flipping a coin with his neck. The valley doesn't hand out trophies. It hands out afternoons. And every so often a bill two men are better off spending on the rider they almost broke.
The Aspen Gran Fondo rolls Saturday, June 27. Thirty-six, sixty-two, one hundred and three. Pick your suffering. Sign the waiver. Read it first.