Potential answers for "Bootlegger's foe"

⭐⭐⭐⭐ TMAN
⭐⭐ FED
⭐⭐ PIRATE
⭐⭐ HOOCH
⭐⭐ MORAN
⭐⭐ ELIOT
⭐⭐ JAYGATSBY
⭐⭐ ALCAPONE

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Outlook button   Perelman or Parker, e.g.   Like Oscar envelopes