The pirates steal and go round sailing looking for treasure
The look out job is to look out for pitates and storms.
There have been several "Sandy"s and "Roberto"s in baseball. Two of the more famous were Sandy Koufax, a pitcher for the Dodgers in the 50s and Roberto Clemente of the Pitates in the 60s.
Oh, dude, like, a skull and heart tattoo can symbolize the duality of life and death, you know? The skull represents mortality and the heart symbolizes love or passion. So, it's like saying, "Hey, I'm deep and complex, but also, I like to keep it edgy."