Potential answers for "Wearing a wire, perhaps"

⭐⭐⭐⭐ MIKED
⭐⭐⭐ SPY
⭐⭐⭐ BRA
⭐⭐ MASKED
⭐⭐ MOURNFUL
⭐⭐ PATIENTS
⭐⭐ TEAMMATE
⭐⭐ BARB
⭐⭐ MOURNING

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The early one gets the worm   He rooms with Ernie   Drug bust figure, informally