Answer: JAILBIRD

AnswerCrossword Clue
JAILBIRD"Avian" for whom flight is often futile
JAILBIRDCooler resident
JAILBIRDConvict
JAILBIRDCon
JAILBIRDCooler dweller, or a novel
JAILBIRDPen resident
JAILBIRDPen dweller.
JAILBIRDMatt Ward song about escapee?
jailbirdperson who is or has been confined in jail; convict or ex-convict
jailbirdan inveterate convict, also GAOLBIRD