Under The Skull & Cross Bones Connection - The Hollow World Box Set & The Isle of Dread

'Hundreds of miles from the mainland, surrounded by dangerous waters, lies an island known only as the Isle of Dread. Dark jungles and treacherous swamps await those who are brave enough to travel inland in search of the lost plateau, where the ruins of a once mighty civilization hold many treasures - and many secrets! "

For many people the X1 The Isle of Dread By David Cook, &  Tom Moldvay remains the Pulp standard for Expert D&D By Frank Mentzer. According to Frank it would take about two months total to play through as a mini campaign. This has been my experience in the past with the module. But I reread through my original Expert copy & ogling the Tim Truman artwork once again. But it was the pirate illustrations & the overall feel of this TSR classic. My day has been beyond a hectic one & strange thoughts can sometimes creep in at this point. “ Exterminate the Pirates", alternate scenario for D&D module The Isle of Dread, art by Timothy Truman, TSR was something that always seemed on the menu with various players over the years. But why?!
 

I think perhaps these pirates might have a bit of a reputation that precedes them. I thumbing through the Piazza as I sometimes do & stumbled upon this thread about rehabbing the 'Merry Pirates' of the Hollow World box set. 
But it was member cab's post that got my creative juices flowing;"cab wrote:No, I wouldn't go down that route, I'd go the other way...

A whole nation of pirates can't survive against the might of empires, at least, not indefinitely. They'll fight just as much amongst themselves as with outsiders, they'll ultimately die out. Which isn't the point of the Hollow World 

Give them a technological edge; renaissance or even better style square rigged vessels, give them speed and maneuverability and an arms advantage and they survive. Not only that, they are the scourge of their part of the Hollow World, a force to be feared, the story to scare children with."

Let's take this at face value & make the 'Merry Pirates' not only scary but downright dangerous. Havard Blackmoor bless his heart got the second part of this adventure element almost into place for me;  "Many Merry Pirates are actually brought into the Hollow World with their memories intact. I could see scenarios where the PCs are captured by Pirates only to have the Captain secretly inquire from them about the state of things back in the old country " What if the 'Merry Pirate' kingdoms are actually using the Hollow Earth as a sort of secret nation base? What if their black wizards are actually using elemental planar gateways to come & go from the Hollow World as they please? I see the 'Merry Pirates' as a bunch of murderous opportunities & cut throats raiding where & when they will.

'The Merry Pirate' nations & floating islands are made up of a mix of Hollow World & Mystara races & mixed members. These groups never have made a unified front but might at some point. But the Sea of Dread was mapped out in X1 & that's where the other Hollow World connection comes in. In the Vaults of Pandius Free Mystara resource Sea of Dread there's an article called Pirate Lords of the Sea of Dread by Colin (LordJuss) Wilson. We get the low down on some of the Sea of Dread's worst of the worst sea scum.. You can download Threshold issue #3 here. 

The  Storm of Korotiku guarantees a fresh supply of fodder for the Merry Pirate nations as many pirates find themselves on the strange shores of the Hollow World. 

What if the Merry Pirates' are not simply raiding the Hollow World? The Island of Dread is now a part of the Elemental Plane of Water & partially exists a higher dimensional or planar location. In Threshold Magazine Issue 4: The Sea of Dread we get Advice for traders in the Sea of Dread by LoZompatore which offers some interesting insight into the forces at work in this legendary oceanic location. I think that the connection between the Pirate Lords of the Sea of Dread & the Merry Pirates goes much deeper. I personally think that they've been taking full advantage of Mystara & the Hollow World's oceanic connection to the Elemental Plane of Water for centuries.


Ocean Encounter: Sea Hydra, by Timothy Truman,
 from D&D module X2: The Isle of Dread, TSR, 1983.

Infact in my own home campaigns I've been using the 'Merry Pirates' to raid the seas of Greyhawk for years. These pirates have spies, diplomatic aids, & ties to the Dullstrand  a region on the eastern coast of the Flanaess. Known for the many colourful smugglers, pirates, and fugitives that use its coast and ports as a refuge from authorities. In other words the perfect location to blend into the background of Oerth.

But the connections don't stop there according to the wiki entry on Dullstrand;

"For players utilising the 1980 or 1983 edition of World of Greyhawk, the Dullstrand is a silent partner of the Iron League, and this setting can be used to explore the theme of righteous rebellion against the corrupt, decadent and cruel rulers of the crumbling Great Kingdom and their minions.^[1]

For players who use later "post-Grehawk Wars" versions of this campaign world, the Dullstrand is affected by the attempted takeover of the entire southern Flanaess by the Scarlet Brotherhood, and can be used as a benchmark of the Brotherhood's overall success or failure of their continental ambitions.

In addition, Dullstrand can be used as the quintessential "lawless town" of noisy taverns and bar fights. Using the Dullstrand as a setting also allows dungeon masters to move their campaign away from a traditional northern European land-based setting to a warmer climate and themes involving ships, piracy, and smuggling, and encounters, both land- and sea-based, with pirates and buccaneers." 

Alright so I've talked about 'The Merry Pirates' as an actual nation level threat but what are the OSR connections. I've used them as enemies in both Lamentations of the Flame Princess & as raiders of absolute horror in Astonishing Swordsmen & Sorcerers of Hyperborea. These lightning raiders appear on the horizon. Attack various nations vessels & then vanish into an elemental  storm. 

The Merry Pirates are going to take full advantage of their upper hand in any campaign setting. Fast ships, lightning raids & tactics, strength in numbers, fast ships, pillaging & plundering, & quick escapes. The Isle of Dread is possibly simply another hide away for them on a string of such planar pirate hide outs.
I've used these pirates in a number of very unexpected encounters including recently in my Amazing Adventures campaign. With the 5th edition Amazing Adventures Kickstarter winding down I might be using them soon then I was expecting. Never mind though let's get back to the Hollow World for a moment. Issue Nine of Theshold magazine fills in a lot of the gaps of the Hollow World including valuable information on The Lighthouse’s Guide to Unknown Cultures: The Floating Continents of the Hollow World. This could lead to some very dangerous encounters with the Merry Pirates & their steel!