gentleman of fortune—(euph., dated) a pirate:
- By a “gentleman of fortune” they plainly meant neither more nor less than a common pirate.
man of fortune—a person possessing great (usually inherited) wealth:
- A sailing club consisting of four or five young men of fortune, have conducted the annual Regattas.
Note: The expression does not correlate in meaning with the phrase fortunate man—a man favored by fortune; a lucky person:
- He was a fortunate man, learning from her to embrace the simple joys of everyday life.