Possible Clues:

• Handled, as a case
• Had a sample of
• Police "Though I've ___ before to tell her of the feelings I have for her"
• Wasn't lackadaisical
• Took a crack at
• "I ___ so hard" Linkin Park lyric
• Took a shot
• Sipped uncertainly
• Bound to imprison ring-leader that's prosecuted
• ___ and 14-Across (reliable)