| Blackhat |
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I ended up creating a "pecking order" type mentality in the shackles based upon reputation.
Council Pirates.
Free Captains.
Other established pirates.
Newbies.
PCs are always free to go to a port in the shackles, but without a dangerous rep, they are anyone's meat. This gives incentive to climb the ranks. If players still insist on going, use some role playing in port to bring it up- merchants treat them badly, bartenders ignore them, whores laugh at them, other pirates (Gortus Svard!) pick fights, etc.
Also, it is noted (somewhere...) that most free captains are "sponsored" by other free captains. Going it on your lonesome is supposed to be difficult and dangerous... and fun for evil GMs everywhere.