Betting
A wager between Samson and his Philistine companions during his wedding feast supplies the one extended episode of betting in scripture.
Samson's Wager at Timnah
At the seven-day feast, Samson stakes thirty linen garments and thirty changes of raiment on a riddle put to thirty Philistine companions, with the same stake riding the other way: "Let me now put forth a riddle to you⁺: if you⁺ can declare it to me within the seven days of the feast, and find it out, then I will give you⁺ thirty linen garments and thirty changes of raiment; but if you⁺ can't declare it to me, then you⁺ will give me thirty linen garments and thirty changes of raiment" (Judg 14:12-13). The companions accept: "Put forth your riddle, that we may hear it" (Judg 14:13).
The riddle itself runs, "Out of the eater came forth food, And out of the strong came forth sweetness" (Judg 14:14), and for three days they cannot solve it.
Coercion and Resolution
Unable to win the wager outright, the companions threaten Samson's wife: "Entice your husband, that he may declare to us the riddle, or else we will burn you and your father's house with fire" (Judg 14:15). She presses him through the seven days of the feast, and on the seventh day "he told her, because she pressed him intensely; and she told the riddle to the sons of her people" (Judg 14:17). The men of the city return with the answer in the form of a counter-riddle: "What is sweeter than honey? And what is stronger than a lion?" Samson replies, "If you⁺ did not plow with my heifer, You⁺ did not find out my riddle" (Judg 14:18).
Samson pays the wager by violence rather than from his own goods: "And the Spirit of Yahweh came mightily on him, and he went down to Ashkelon, and struck thirty men of them, and took their spoil, and gave the changes [of raiment] to those who declared the riddle" (Judg 14:19).