The gambler’s fallacy is the mistaken belief that a certain outcome is more or less likely to occur, given a previous series of outcomes. For example, if you flip a coin and get four tails in a row, the gambler’s fallacy would suggest a greater chance of heads on your fifth flip. In reality, the odds remain 50-50.

And so it went for Bruce Miller and me on our four-year Diamond project, when, day after day, season after season, we expected a different outcome than the usual: getting schooled. Whether by rain, cold, or lightning, cryptic cruxes, altitude or exhaustion from the four-hour “approach” to the summit of Longs Peak, we got the beat-down more often than we made any tangible progress.

Alas, the chance of failure remained just as likely, even after 50-plus days of effort.

Gambler’s Fallacy follows the first three pitches (5.6, 5.9, 10a) of Hearts and Arrows (also shared with Enos Mills Wall), then takes an 11a crack to the base of a huge, shaded, right-facing corner. From the base of this Winter Wall Dihedral (first freed by Jeff Achey and Leonard Coyne in 1980—the hardest Diamond free pitch back then), the next 300 feet are overhanging, with pitches of 11d, 13b, 12b, and 13a. This is now the steepest Diamond free route. A final, vertical pitch follows a razor-thin 12d traverse into a sequential finger crack to the top. It wasn’t until three years into it, during the summer of 2019, that we finally deciphered the crux pitches enough to know, at the very least, the route was possible.

I felt ready to redpoint before Bruce did, so on August 9 he supported my effort by belaying and jumaring while I led. Neither of us had led the hardest pitches before, but countless solo toprope attempts had prepared me well. As nervous as I was—concerned that having to repeat any pitch would substantially diminish my chance of sending—I somehow managed a no-falls ascent.

But if the Diamond was the protagonist in our four-year journey, Bruce was the real hero. On August 22 he sent through pitch seven (including pitches of 13b and 12b), which, even at a roadside crag would have been one of his best climbing days ever. The 13a “Roof Pitch” above spit him off three times, but that only seemed to sharpen his determination.

We aided to the top, bivied below Chasm View, hiked to the top of the wall the next morning, and rapped in. Bruce made quick work of the Roof Pitch on August 23, and he sent the 12d final pitch in a couple of tries.

His free ascent over two days, though not ideal, was truly heroic. Did I mention that eight days later he would turn 57 years old? I’ve seen Bruce dig deep on many occasions, but this route required of him a long-term level of effort and commitment several magnitudes greater than anything else has. I know this because the same is true for me.

In the end, the pitfall of the Gambler’s Fallacy is also its upshot: Our dozens of previous failures had zero effect on our eventual chance of success. How about that?

— Chris Weidner

First ascent on The Diamond - Longs Peak (14,255'), Colorado from Louder Than Eleven on Vimeo.