Possible Clues:

• Risk-it-all wager
• All-out Vegas play
• Follow-up wager depicted in the starred clues' answers?
• High-stakes gamble, and how the answers with circles can be read
• High-stakes wager
• Poker loser's offer
• Bettor's offer
• Offer from a desperate sort, perhaps
• Risk-it-all bet
• Call in many a betting game