to play at any game of chance for money or other stakes. to stake or risk money, or anything of value, on the outcome of something involving chance: to gamble on a toss of the dice. verb (used with object), gambled, gambling. Betting; wagering. Results in either a gain or total loss of wager, the money or asset put up. Neither risk-taking nor investing, nor like insurance. Risk taking or speculation takes on substantial short-term risk to potentially get high gain. Investing uses property or assets to potentially increase in worth, securing long-term capital gains. Insurance can prevent financial loss but has no way to gain.