Possible Clues:

• Elude
• "eads I win, tails you ___22
• Not prove victorious
• Shake, as a police tail
• Gamble away
• Finish last, say
• Blow, as a lead
• Emulate the 18-Down
• and 14 Down: Suffer maybe when paper is accidentally chucked out and turn very irate
• Mislay — fail