A note on pirates

The entry for Men (Pirate) directs you to choose the ship type of the fleet, and extrapolate from that the numbers of pirates and level 1+ headmen. You can list the fleet types out in order of ascending threat, like so:

Ship Type Num Max Average
– F4, 0-level Mercenaries –
Sailing, small 1d3 36 24
Sailing, large 1d3 60 40
– F4x2, 0-level Mercenaries –
Boat, River 1d8 80 45
– F5x4, F4x7, 0-level Mercenaries –
Longship 1d4 300 188
– F5x5, F4x9, 0-level Mercenaries
Galley, small 1d4 400 250
– F11, M9, F8, F5x10, F4x17, 0-level Mercenaries –
Galley, large 1d3 750 500
– F11, M9, F8x2, F5x16, F4x27, 0-level Mercenaries –
Galley, war 1d3 1200 800

I can’t help but feel the Sailing Ship fleets are a little lacking- they sail the most dangerous waters in the most advanced vessels, with a single leveled fighter among them. This may be by design, but if not: If the monster entry was changed to read “There will be one 4th level fighter present per 30 pirates or ocean vessel, and one 5th level fighter present per 50 pirates or ocean fleet,” it would at least goose them up to a spot between River Boats and Longships.

Maybe the sailing ships have mages or clerics instead to help with sea navigation?

If I remember right, B/X puts Clerics amongst buccaneers, who are basically pirates with neutral alignment. Another option would be to bump the number of ships up a little.

Clerics would be worth their weight in gold to pirates, not just for navigation but healing, food and water etc. Ships could stay at sea longer.

Maybe I’m just weird, but Sean’s comment, along with the historical penchant for raiding monasteries that various vikings demonstrated, makes me picture pirates raiding temples to carry off clerics (along with the other loot) and then keeping them chained in the cockpit as part of the equipment of the ship (rather than as part of the crew). As a side benefit, this provides player character pirate hunters with a possible source of additional retainers.
Re: Charlatan’s basic point: I’m inclined to agree. The 250 pirates on a small galley (perhaps mostly rowers, not pirates?) are not likely to be as capable, individually, as the sort of more daring pirates in the crew of a large sailing ship. Making the sailing ship pirates more elite seems like the way to represent that. More generally, there’s a distinction between the crew as in the people needed to do the work of sailing a ship and the body of pirates on a ship. I think during the Age of Sail that pirate ships carried many more crewmembers than needed to sail the ship, since they needed to be able to fight and to crew prizes (I know that privateers and naval vessels of the period did, but I think that extends to pirates as well). Conversely, the total company of a galley would typically have many rowers who weren’t really combattants (and may have been slaves). So maybe the solution is to distinguish between the number of pirates on board (which for a sailing ship would be the total complement, and maybe the same for river boat pirates, but might be a tenth the number on a typical galley) and the non-pirate crew (perhaps 0 for a sailing ship, but maybe 90% for a galley). We can then make all of the pirates the elite 1st level characters, not the normal 0th level characters who don’t choose to pursue a life of danger, and make the complement of leaders relative to the 1st level pirates. At that point, a small sailing ship has a comparable combat company to a small galley, and a large sailing ship comparable to a large galley.
On a tangential note, a Roman historian I game with tells me that during Roman periods, at least, a great deal of the enormous amount of piracy in the Mediterranean was based on people in small villages near the coasts launching raids in small boats on merchant ships nearby–fishers and similar ordinary coastal folk who added an amateur sideline in piracy, and might turn pro if they were successful enough. That might be represented well enough by noting that river boat pirates are also active in coastal operations, although I think the river boats described in the game are too large to represent the small coasters and fishing vessels used by coastal pirates.

Sorry, I should have explained my chart better: 250 is the average number of pirates in a small galley pirate “encounter” (1d4 galleys, each with 100 pirates aboard).
If you only count marines as pirates, the small galleys would have around 20 pirates already. So that change would move the sailing vessels up relatively, but by significantly depressing the potency of the fleets ahead of them. Longships become as formidably staffed as War Galleys. You also move the presence of Pirate Kings off the encounter list completely (which is fine; they’re clearly leading a Domain of Chaos at level 11!), as well as the level 8 leaders.
In my mind, you have some targets for crew capability like so:
River boat pirates need a chance to take down river travelers.
Longship pirates need a chance to survive sea encounters, and raid villages and towns.
Galley pirates need a chance to survive sea encounters, raid villages and towns, and fight fleets of other galleys.
Sailing ship pirates need a chance to survive open sea encounters, raid merchant ships, and fight other sailing ships.
In the case of open sea stuff, you have to take survivability with a grain of salt (dragon turtle?). But I’m thinking of merchant ships, which I would be inclined to staff as a merchant caravan (Fighter 5 captain, 2 Fighter 2/3 lieutenants, 20 Fighter 1, lining up nicely with the complement of a large sailing ship).

Thanks for noticing this discrepancy. This was legacy data from B/X. I’ve now corrected it as follows:
Pirate: A pirate fleet may be found on any body of water, whether lake, sea, or river. The fleet size depends on the water vessel. Riverboat fleets number 2d4 ships; fleets of small galleys or small sailing ships number 1d6; fleets of longships number 1d4; fleets of large galleys, war galleys, and large troop transports number 1d3.
The crew number is determined by the ship crew requirements described in Chapter 6, and will include a full complement of marines, rowers, and sailors. Marines and sailors are always pirates, as are any rowers on riverboats and longships, but the rowers on galleys are captive slaves. All pirates are armed with swords and leather armor. 40% are also armed with crossbows or shortbows. Slaves are never armed and will not fight.
There will be one 4th level fighter present per 30 pirates, and one 5th level fighter present per 50 pirates. Pirate fleets of less than 300 will be led by a pirate captain of 8th level; forces of 300 or greater will be led by a pirate king of 11th level. A pirate king has a 75% chance of employing a mage of level 8+1d2.
This correlates to corrections made to Troop Transports under Equipment:
Troop Transport, Large: This is a large sailing ship reinforced for war and modified to carry additional troops. It can carry 50 marines in addition to its normal complement of 20 sailors.
Troop Transport, Small: This is a small sailing ship reinforced for war and modified to carry additional troops. It can carry 25 marines in addition to its normal complement of 12 sailors.