In "The Outcasts of Poker Flat," Mr. John Oakhurst and Tom Simson met while gambling before meeting again on the trail.
After Mr. Oakhurst and the others are kicked out of Poker Flat, they head to a new settlement. On the way, they come across Tom Simson, whose nickname is "The Innocent of Sandy Bar." He seems to be a nice young man who almost got more involved in gambling.
Mr. Oakhurst and Tom met across a gambling table. Mr. Oakhurst won $40 from Tom, which was the entire amount the young man owned. After things were done, Mr. Oakhurst returned Tom's money to the young man and told him not to gamble again. He told him that he wasn't a good gambler.