And back then, being a pirate to a kid was probably the equivalent
of being an astronaut or sports star to today's youth - just about
the coolest thing to be imaginable.

Look what Mark Twain had to say on the subject:

“Now and then we had a hope that if we lived and were good, God would permit us to be pirates.”

And we still romanticize pirates - just look at the Pirates of the
Carribean series.

Life was pretty sucky for most people in the old days. To see a group
of men - and sometimes even women - roaming the seas in apparent
freedom doing as they please, who wouldn't find that attractive?