Mr. Oakhurst thinks that making camp on the way to Sandy Bar is a bad idea because their exodus from Poker Flat is made at an inopportune time, in the stare of winter. For, the journey to Sandy Bar is long, it is late in the season, and they must cross a steep mountain range, the Sierra Nevadas, a crossing that is, at best, "a day's severe travel." Naturally, as a gambler, he would calculate the odds of any decision.
Mr. Oakhurst, whose name suggests strength, is "philosophic" and he firmly believes in fate. In addition, he possesses what the others lack: a "calm equanimity." After the others, who lack his wisdom and have been drinking, insist upon stopping, Oakhurst looks up at
...the gloomy walls that rose a thousand feet sheer above the circling pines around him; at the sky, ominously clouded; at the valley below, already deepening into shadow.
His profession makes Oakhurst cautious and always alert to changes around him since danger can easily make its stealthy way to him. He know that stopping is a mistake.
Certainly, he has acquired a wisdom that the others such as the complaining and selfish Duchess and the reprobate Uncle Billy clearly do not possess. Instead, this opportunistic scoundrel makes off with all the provisions in the night. It is then as they are stranded in the snow without animals or food that the gambler Oakhurst realizes all the odds are against them, just as he feared earlier.