Although it's been many years since I've touched on the idea even in passing, I've long thought that the two books, The Pirates Guide to Freeport and Five Fingers: Port of Deceit are two great books to read kind of side to side and to compare and contrast, since they both deal with the idea of adapting the Golden Age of Piracy into D&D in one form or another. Both are books that came out in the midpoint of the 3.5 run, before we had any idea that 4e was waiting in the wings, but after we'd digested the somewhat bitter pill of 3e advancing to 3.5 too early and unnecessarily. EDIT: Actually, I think 4e's development might have been just announced, right as the Freeport book was coming out, although their decision to make it system-less was a coincidence that seems fortuitous in immediate hindsight. It literally has no game statistics of any kind, and is not meant to belong to any system. A number of companion pieces came out for it, giving exactly that; specific game statistics. I can think of at least 4-5 that were released, although I only really used the d20 one (later renamed the 3rd Era.) That said, even when I was actually using that system, the companion books were not nearly as evocative, fun to read or even as useful as the generic, system-less one.
Although I say that the Freeport book is system-less—and it is—it's clearly a D&D book. Beyond the system, D&D has become a kind of meta-setting, almost its own unique subgenre of fantasy, that has a number of pretty instantly recognizable tropes and conventions, and Freeport hits all of them without fail, even without a single rule. In fact, it does so significantly better than most novels that are written specifically to be D&D novels, many of which are simply fantasy novels with some placenames and characters that sound D&Dish. This isn't just a commentary on the races and their characterization which is often the first go-to D&D identifier (although it is that), but you can even see through the text descriptions in Freeport to see the D&D classes, the magic item economy, the type and frequency of magic available, the pantheon of D&D-ish pagan gods, the prominent position of adventurers and former adventurers as a kind of very specific caste of movers and shakers, and more details both broad and specific that are shot through the book through and through.
As a guy who has largely rejected the D&D meta-setting in many ways—and after the behavior of WotC with regards to the brand, am more and more likely to reject even more of it going forward—this is a negative of the book to me. To be fair, most of the systems that the companion volumes were written for are deliberately very D&D-ish—d20, True20, Castles & Crusades, Pathfinder, etc. (Savage Worlds and FATE being admittedly potentially very different.) Although there is much I can borrow, there's much I have to reject, or rework to be useable in the this format.
I also often have a problem with the tone. Freeport alleges to bring a horror tone, but what it really does is have a bunch of wink and nod references to Lovecraftian elements. I've come over the years to see Lovecraftian gaming as more like a Disney ride where you take comfort in seeing familiar Lovecraftian elements as you pass by in your ride-car rather than something that successfully evokes a tone of actual horror. If your Dark Lord has tentacles and the writers make gratuitous reference to madness (but otherwise do little to show it) then ultimately he's still just a Dark Lord, and by now, almost as cliché as a Sauron-like dark wizard. The writers' attempts to inject other tongue-in-cheek references and puns pretty liberally through the book strengthen this impression, and the Lovecraftian horror becomes little more than a theme park caricature of actual horror of any kind; Lovecraftian or otherwise.
Which is fine. I have my own fairly strong opinions on how to be successful with horror in a dark fantasy game, and I certainly think that playing straight up D&D (especially of the 3e or later varieties) with flippant and almost satirical references to Yig, tentacles, weird angles and other Lovecraftian buzzwords doesn't get you there. But that doesn't mean that Freeport doesn't have plenty of good material to borrow and adapt, merely that it can't be used right out of the book as is if you want to actually have the tone and themes that the book claims to be promoting.
I also think that the development of elements outside of the city of Freeport itself is rather poor. I don't just mean the chapter on "The Continent" which was a new development for this book, but also anything else on the nearby islands that are part of the Freeport orbit. The islands themselves are pretty tiny, and the idea that they are chock full of dangerous predators and monsters—especially after the somewhat silly "Great Green Fire" event is verisimilitude breaking. In an area about the size of a few housing developments together in my suburban town, there's supposed to be a bunch of predatory animals and monsters, somehow supporting themselves on... something?
The ideology of the Freeporters and their rivals in the even more ridiculous Libertyville is also laughably absurd. You're better off using the city, and ignoring everything else in the book. And that's if you want a very specifically D&D pirate city that has some of the charm and all of the flair of the original Pirates of the Caribbean ride at Disneyland. There's very little outside of the city that I actually like.
The Five Fingers book, on the other hand, is a different creature altogether. I don't think its any more or less usable than the Freeport book as written (at least not for the purposes that I'd use it) it somehow manages to be the same level of useableness while being the opposite of Freeport on almost all of the points mentioned above.
Five Fingers isn't a system-less book, and was never meant to be, although to be fair, not a lot of rules are present in it either. There's some stats of a few NPC characters, a small selection of prestige classes, a handful of other things like Knowledge (local) check result tables, and stuff like that. There are a few side-bars (and by bars, I sometimes mean several pages at a time) of subsystems that D&D 3.5 doesn't have, which Five Fingers introduces, including a chase mechanic, and a detailed bribing mechanics subsystem. But even if you skim this stuff, you're only taking off about ten pages of a 200 page book, so it's hardly like that's the bulk of it.
However, where Freeport—while being system-less—was very clearly a D&D supplement, and even without rules it screamed D&D all the time, Five Fingers is curiously an actual D&D supplement that doesn't often feel like D&D. That's because its an integral part of the Iron Kingdoms setting, which by this point, and developed enough to feel quite a bit different from D&D. By this time Warmachine had been out (in its first iteration) for a couple of years, and had partially served to drive the setting away from its dark and gritty (ish) D&D roots from back in the Witchfire Trilogy days where it started. This means that I don't have to worry about dealing with D&Disms that I don't want, but it does mean that I have to work harder to make it not feel too Iron Kingdoms! Because it's heavily integrated into the setting, and the events taking place in the setting, there are a lot of elements that would be different to use if you don't have something like Cygnar just next door, an occupied Llael flooding the city with refugees, the specific intrigues between the Cathor and Mateau families, the specific intrigues between the Khador and Cygnar superpowers who stand in somewhat transparently for Soviet Russia and Cold War America respectively. You need something like Cryx, you need Thamarites, etc. to make it work without extensive remodeling. Although in some ways Iron Kingdoms fits Dark Fantasy X better than D&D, there's still an awful lot of very specific setting stuff that I need to be on the lookout for. And they don't make any effort to reduce that for greater flexibility, because unlike Freeport, Five Fingers isn't meant to be a modular and insertable into any other setting, it's specifically meant to be part of its own setting.
That said, although both works would need quite a bit of reworking to be useable, Five Fingers probably has more material that I could use. The horror elements are more horrible than in Freeport. The organized crime stuff is tons better and is really the best element of this book. Although it still will need some adaptation to not be Iron Kingdoms specific. In addition, some of the other appendix material is really well done; stuff like the list of NPCs (I'll trawl through that to create my own list, probably—I really like Iron Kingdoms naming conventions; they sound vaguely Olde English without being exactly so.) The list of businesses is also extremely useful. I'd put customized material, drawn at least in part from both of these on the inside of my GM Screen.
I'd also utilize a lot of elements drawn very directly from the four crime lords of Five Fingers. They make the two crime lords of Freeport look like cartoon characters in comparison. I also feel like the occult/horror elements are really well done compared to the flippant rewarming of Lovecraft that Freeport gives us, but I'd probably have to rework them to not be so completely Iron Kingdoms-esque, and honestly there's not quite as much content for this in the book as you'd think anyway.
One thing that is common to both books is that while the theme is clearly "pirates", the book offers relatively little in terms of dealing with actual piracy, sailing, or anything else on the sea. Rather, they are ports that are (sorta) frequented sometimes by pirates, but they are clearly urban sourcebooks that detail a city that is rife with organized (and unorganized) crime. They both are more The Godfather in many ways than they are anything pirate-themed. This doesn't mean that they are bait and switch products, but if you really expect more piracy and find that pirates are only characters that you'd occasionally meet while in port, you might be disappointed. Personally, I prefer the urban crime more than high seas crime anyway.
