Possible Clues:

• Prized cigar
• High-quality cigar
• One of The Young Ones opening act for One Direction living on the island
• Like Castro
• Castro, e.g.
• Like Desi Arnaz, by birth
• From Havana, say
• Jose Canseco, by birth
• Like many Miamians, by birth
• Fidel Castro, e.g