I began my journey here at Black Gate telling everyone that I was a gamer, a lifer as I put it, and that’s something I just can’t seem to shake. It all began when I was in junior high school, very early eighties, and with that damnable Red Box… but that isn’t to say that there weren’t thousands of others who did the same things I did concerning the D&D hobby in their school years.

What makes me different is that I still play today, but again, I’m not alone in that either as sites like Dragonsfoot help link like-minded, and yes ‘old’, gamers into an online world where they can still discuss the trials and tribulations of gaming life.

[Note: True story, I was on Dragonsfoot last week and someone asked a question about the module B3 Palace of the Silver Princess. I answered the question and added a bit about the nasty trick in the room in question. Bam! I get jumped all over for not posting a spoiler alert on my answer… for a thirty-year old D&D module! We old gamers take our hobby seriously I guess.]

But back to the point, I salute anyone who can continue a hobby for thirty years. Like most things started in youth most people will simply grow out of such simple passions. For me, however, a deep love of history and art kept me involved in gaming, along with a good deal of chance.

To tell this story, I’m going to provide a history, but for the art side of things I’ve gone to great lengths to recruit all the friends I’ve made in this industry the past two years as a visual guide. To me there is a symbiosis involved, and one cannot truly appreciate the tale without the visual additions, because any good fantasy tale deserves some wondrous illustration.

I’ll begin where any good role-playing story should, my first character, the D&D Basic ‘Red Box’ Edition fighter, Sir Fleetwood.

[Note II: I asked Frank Mentzer, who wrote the Red Box, if there was any story behind this class example character and he replied as follows: ‘Fleetwood was a fighter PC (okay, actually a ranger) in my Lake Geneva AD&D campaign, c.1981-85. He was regularly played by TSR Editor Jon Pickens for most of that period (along with other players from TSR including artists Keith Parkinson & Steve Sullivan, Jim Ward, Skip Williams, and many more).’]

Like most of those who played this young, I found something I liked and mimicked it. I mean how many people played in their tween years and had a wizard named Gandalf? More than most would like to admit I bet. Anyway, I reached into that Red Box with all my imagination and found Jeff Easley’s picture of the Frank Mentzer ‘Sir Fleetwood’ fighter the most inspirational thing I could have hoped for. What to do next? Why roll him up of course. If someone asked what my fighter looked like, I’d just open the book and point him out. Simple enough, right?

Now, as characters go Sir Fleetwood followed me through the better part of 8th and 9th grade, his exploits becoming my first leg into gaming as a whole. I was gaming with a new friend, Mark, and he was a tireless and creative DM with access to all the adventures his older brother had collected since the 70s. In this target-rich environment Fleetwood quickly found himself leading a company of the usual suspect classes and races as he delved through a dozen classic TSR modules. Three colored boxes later [Expert, Companion, and Masters] and he’d maxed out his class like only a true Monty Hall character can.

This story is most likely a mirror to many players introduction to role-playing with perhaps a bit more experience points involved. I point this out because hobbies are all about transitions, and most don’t survive even a single life-changing event. If you don’t fully recognize what I mean, I’m going to start breaking things down into transition blocks as we progress through this tale.

Transition One: Tween to Full Teenager. That two year stint with Sir Fleetwood spanned the transition between my tween youth of junior high and my induction into the freshman fraternity of high school. I’m sure this school jump marked the end for many role-players, but to me the passion continued as I did something most gamers at that age wouldn’t, I spun a tale where I married the character of Sir Fleetwood to the cleric of his adventuring party, M’Lady Madonna [yes, Like a Virgin made me want my own ‘boy toy’ so how could I resist… I mean I was a walking teenage hormone after all!].

Now I’m not sure what it is about me and marriage, but I’ve always wanted to be married, so it was natural I guess to have my most powerful and successful character get himself hitched. I mean at fifteen years old I sure couldn’t have gotten married myself, so why not live vicariously through my paper and pen avatar, which in many ways is what role-playing is about in the first place. Marriage, however, if practiced by other role-players with their favorite characters most likely stopped there, but not with me…

I had a vision, a creationist dream of world-building that probably rose out of my love of fantasy literature and the desire to be a writer myself. To build such a world, especially as a historian, I needed a timeline, and that tiny piece of written information was more a foundation to this transition than any grand world map I could create. You see, a timeline is begging to move forward, to be advanced, and as I looked at the page of world history I’d created it just never seemed like it was enough.

During this stage I met a friend who had never role-played before and was hesitant to begin something this involved when it was obvious my own characters were so powerful and entrenched. My remedy to disarm his trepidation? I offered him a chance to start his character with a bunch of cool stuff that Sir Fleetwood had collected in his adventures. The only question remaining was, ‘how did he come by all that equipment and magic?’ The obvious answer, the character would be the child of Sir Fleetwood and M’Lady Madonna.

This, for all you scoring at home, was the supreme catalyst. In bringing in this new role-player and character I just advanced my world’s timeline more than eighteen years and created a second generation of a fantasy family.

Sir Fleetwood’s son was named Philip, after the player who played him, and during the summer after my freshman year we played many adventures with this next Fleetwood. Unfortunately, Phil, like many people who fall into the genre quickly also disappeared just as fast when the true pressures and new opportunities of high school came into play.

By my sophomore year Phil was gone to bigger and better things and I was left with a void best filled by my first long-term relationship with a girl…

Transition Two: Boy Meets Girl. Okay, here’s the crux. In the 1980s the word geek wasn’t what it is today. There was no Big Bang Theory, no Anime, and certainly no MMORPGs. That’s not to say there weren’t geeks, it’s just that they weren’t as socially acceptable as they might be today. Even in 2011, however, it’s probably pretty tough to walk the halls of a high school with a 4E Players Handbook and a set of Magic cards and get women. The transition from game playing youth to awesome teenage stud is a trap that’s killed its fair share of role-players.

This meant that if I wanted to conform to the rights of passage and get the girl, I needed to be like everyone else. Perhaps this is what happened to Phil, but whatever the case, I put away my characters and books from the eyes of my peers and collected a group of socially acceptable friends. In reward for this new persona I gained popularity and a dance captain girlfriend… but like a super hero of old, I just couldn’t give up my secret identity.

On the weekends I would blatantly lie, say I was hanging out with known cool friends at school, and instead race over to game with my trusty sidekick Mark. Why? I guess I wasn’t ready give up the pursuit of adventure, and by my junior year I decided it was once again time for a Fleetwood to be the center of a campaign as my timeline and history grew. So another generation passed and Thalos Fleetwood, son of Philip, was brought into the world of his forefathers from the newly minted pages of the Unearthed Arcana.

Thalos would be my companion through the end of my high school career. He was blessed and cursed by being the character that helps you move from Monty Hall gaming to a more realist way of true campaigning. Magic items dwindled, experience was harder to come by, and each level you gained was more a celebration of something hard won than simply a number that is ever on the rise. But even as my mind grew to the possibilities of a more fundamental way to game, my youth slipped into another transition, this one a waiting assassin for most hardcore gamers that had survived as long as I had.

Transition Three: College. I remember well preparing for college. My life was in turmoil as my long-time girlfriend broke up with me and I was trying to rediscover who I was. I chose a school far from home, far from friends, and when I got there I promised myself I was done being a child, done with fantasy, and certainly done with role-playing. For all intents and purpose this should have been the end.

Three weeks into my first semester on dorm I hear dice rolling in the room next to me. Gamers… and you know what, they were doing it all wrong! They didn’t care about history, or worlds, or heaven forbid character backgrounds. For the love the game I needed to step in right? RIGHT? So I did, I walked in, threw their woeful DM to the curb, and started showing them role-playing as I knew it.

By luck and chance I’d survived the purge of youth, and when I rekindled what I thought was broken I traveled back on vacations to my home town and resurrected my world and the Fleetwoods inside it.

Mark, ever faithful as any true friend could be, was always there and by my second year at college I was ready to take on another generation. Thalos beget Relgar, and I’d now moved into the 4th generation of Fleetwoods.

Now Relgar was an interesting story, because to that point the Fleetwoods were a family on the rise. They’d been kings and powerful lords, but perhaps my own fall from grace and reclamation spurred the idea that the House of Fleetwood should tumble as well. Relgar lost his kingdom and was forced to live the life of a deposed noble in a free city of duelists and rogues.

Like me he was in the wild, without true place, and as the days of my college life dwindled he found love with a vivacious beauty just like I did, but this time all secrets were on the table. I found love, and so did he, another generation of Fleetwoods certainly on the way as transition again knocked on the door.

Transition Four: Work. What do you do after college? Well, you get smacked right in the face by what being an adult means as well as how little your degree counts for anything. This is another stark moment in the life of gamers, and after the freedom of college is ripped away, the need to work for your food and shelter can take the shine off spending hours lost in fantasy imaginings and rolling polyhedral dice.

I moved to Florida, several thousand miles from my home town and gaming friends, but instead of spending my days in full grind mode I used gaming as my release from the monotony of the nine to five, or nine to nine in many cases. Ah the joys of retail…

Actively seeking role-players I created my own role-playing group for the first time, but in doing so I dropped my old world and old Fleetwood ties because there was simply too much to try to relate to a core of new players. Although this wouldn’t be the end of the line for my role-playing days, it could have easily marked the end of the Fleetwoods.

Mark, however, had other plans, and along with one of my other oldest gaming cohorts in crime from junior high, Murphy, the two made an enormous road trip to spend their first week’s vacation from their jobs with me in Tampa Bay playing nothing but the old world D&D.

So came yet another timeline advance, Relgar sending his son Philip II into battle against the dark tides that had helped destroy their kingdom thirty years before. 70 odd years in the gaming universe and a decade in reality provided 5 generations of gaming family. Philip II being a hardcore reminder of true experience earned as he ground out years of hearty campaigns under my watchful eye.

I have often asked myself why my old friends came all that way, but really the writing is on the wall. Mark and Murph made the journey and gave up their only week off because of history, because of a story that was still being written, and that anvil from which we were forged was now strong enough to endure almost any transition, even the next great step forward.

Transition Five: Marriage. As I’ve said above, I love marriage and always have, which is funny since my parents got divorced when I was less than a year old. Perhaps it’s a desire for something you were denied, but whatever the case I married my college sweetheart, and for most role-players sharing nuptials would be another hurdle hard to cross.

If you happen across a prospective wife or husband at the office, in a club, at the beach, or even shopping at the grocery store, it’s certainly going to be harder to explain that on Saturday nights you sit around a table pretending to be elves and wizards.

For me, however, my wife had been indoctrinated into my alternative lifestyle since it was almost acceptable. I mean really, it’s amazing what eighteen year-old young women will let you get away with that twenty-eight year-olds won’t… Whatever the case, I dodged another bullet here simply by the seven years I’d already invested in the relationship.

My commitment to gaming would be tested again, however, as I once again took to the road seeking work.

Transition Six: Moving. Now I don’t know how many people are born, grow up, and die in the same town, but it can’t be too many. My friend Mark is the exception to the rule, but after a year in Florida it was time to move again, this time all the way up the coast to the Baltimore/D.C. area of Maryland.

Moving can be hard on anyone, but it is certainly crushing to the spirit of a role-playing campaign. Forget play-by-email, which never works, because in all reality once you move from a game and group you’re never going back.

It also doesn’t help that the older you get, and the more weighted down with life, the less you want to go to a gaming store and start all over with people you don’t even know. When I went to Maryland I was still a rather spry twenty-six, so I could afford to build again, but this time I determined that I’d have to include my old world no matter how much teaching it would require.

Luckily for me it worked, and I managed to spin new and improved tales about my world and the Fleetwoods into a new group in Maryland while Mark and Murphy made the pilgrimage to play during ‘The Week’ once a year for supplementation.

This new gaming group saw the rise of Philip II’s son Gorwin who went from being a king to a massive power grab for the title of world emperor. Unfortunately it wasn’t in the cards for Gorwin, but that never diminished the fact that he marked a 6th generation of family, and during his reign my world celebrated its 100th anniversary of historical timeline.

I would continue to play Gorwin into my 30s, and then his son Alec as the calendar turned over into a new century. A 7th generation was now on paper and being played.

[Note III: Alec’s sister is Lyssa, the now famed wizardress from Art Evolution]

Alec was an interesting story because he was built from the D20 Iron Kingdoms supplement, was a Pistoleer, and as Fleetwood’s go probably became the most shadowed of them. He was also my first Fleetwood to have been made fully in D&D 3rd Edition, which in itself was another transition as I’d played 1E Advanced D&D for over a decade. I also suspect that as many players might be lost as gained when companies create a new edition, so I guess I survived several possible pitfalls there as I just kept moving along in the game.

When it comes to pitfalls, however, there’s one that I think trumps them all, and it’s possibly the final transition.

Transition Seven: Children. Yep, for the better part of all folks, children will someday be in the cards. What do children leave you time for? Well, nothing… they’ll end up taking it all unless you go to great lengths to nurture yourself as well as them.

My son was born in 2006 and by 2007 I didn’t game anymore in Maryland save for that one sacred week a year with Mark and Murph. Again, without those now-ancient friendships and family lines, I wouldn’t have played at all.

A child, in some insane twist of irony, became both the reason I gamed for twenty-five years and the reason I basically stopped. I suppose a contributing reason to that stoppage lay in the fact that I now had my own lineage, my own heir to the throne, and somehow that diminished the need to go overboard with gaming at least in the short term.

Still, when you do something so long and invest so much into it, putting everything away forever is hard. There has to be some way to fill the void left by what you’ve given up, and for me I might be able to stop my weekly games, but I couldn’t stop building, stop writing, or stop the flow of history in my gaming world.

Eventually Alec gave way to Godwin during a Mark and Murphy ‘Week’ and I actively tried to make it back to my hometown a couple more times a year to supplement that need to game.

[Note IV: I did a calculation once, that if you get together with other RPers for a full week, and play upwards of 16 hours a day the whole time, you’ve put in 112 hours of solid experience-building gaming. In contrast, when I gamed one evening a week, it would be for a 3-4 hour session that would take a full hour to get stared, so maybe 3 hours max would actually make up gaming. Thus, in a full calendar year, minus holidays and missed weeks, you’ll probably get 130 hours of gaming in. That means that by taking that single week, I could get as much experience and role-playing in as I could in a whole year with a standard gaming group.]

Godwin was the 8th Generation and as I took the time to work out his tale and adventures, I began revisiting my world’s history. What had once been a single sheet of loose-leaf paper was now a huge digital file. I’d written out 150 years of history in it, and on top of that I’d created 14 full ‘Ages of Man’ in my world that spanned over ten thousand years.

It was at this point that I began to be intrigued by something I referred to as ‘the founding’, which is to say the place in time where my Fleetwood line actually began. You see, Sir Fleetwood was certainly my first Fleetwood, but I began to wonder how he actually started with a surname, the title of knight, and where in the misty past his people had come from.

To assuage this archeological thirst I petitioned Mark and Murph, who both had ancient family trees as well, to journey to the past and find each of our family’s humble beginnings. To accomplish this we went completely old school, cracking out our worn 1E hardcovers and starting first with just the Player’s Handbook for what would be the true genesis generation.

In these simple campaigns I finally saw the creation of Tyr ‘Fleet of the Wood’, a common woodsman thrust into the fire as a fighter/soldier/and adventurer when plagues swept across his homeland. He would be the true first Fleetwood, the forefather of them all.

Now understand we didn’t have to invest the bank in these characters, we just needed to give them purpose and have the story play out from there. We also took the opportunity to play some classic modules as well, Tyr’s big one being B2 Keep on the Borderlands in honor of the recent passing of Jim Roslof who’d done the cover for that module.

Backtracking in such a way allowed me to relive a portion of my youth. The art of role-playing was now so thick in my blood I don’t see a time when it will ever leave me. The act of playing out this history had a kind of restorative magic to it, something that keeps those who do it young, laughing, and doing things far from respectable as mature men of the community.

So Tyr gained some promise and a surname to give to his son, Vigbrandur Fleetwood, who would have the chance to once again use the Unearthed Arcana for his creation. To test his adventurous metal we included the running of the modules B3 Palace of the Silver Princess and S2 White Plume Mountain as the name Fleetwood slowly grew to renown in a region I called The Free Coast.

By the time I’d joined Black Gate magazine and once again moved, this time to L.A., the gaming family was rounding out. Vigbrandur, now the 2nd generation, had given over to a 3rd generation in Reld Fleetwood. For this generation I could choose a class from any 1E book including Dragon magazine classes so Reld became a duelist. His child would be the link that bound the timeline to the original Sir Fleetwood.

At this year’s GenCon, the convention we now plan our yearly ‘Week’ around, we got to finish our past, and continue the present with Godwin completing the final section of G1-2-3 Against the Giants. So from 1983 to present, 28 years, I’ve played D&D and utilized a single family line to keep my hobby going through a lifetime of transitions.

For those of you who have managed to read this far, I’d like to thank you for taking the time to do so and also offer you an update on my gaming family.

In 2012 my old DM Mark and I managed to get together during the month of August when he was on voluntary layoff from his job and I was transitioning from one job to the next and had a month free as well.  During those few weeks, we once again managed to advance the Nameless Realms timeline with the Fleetwood Family and run a fresh Pathfinder campaign featuring Corvis Fleetwood.

Corvis spent the better part of a year campaigning in various jousting tournaments across the Nameless Realms from Thalonia in the New Kingdoms all the way across the continent to Findalynn in the Principality of Dragmarsh.  It was a grand time for adventure, and it once again reminded me just how important my friendship with Mark is and how two people who have played RPGs so many years together can simply sit down and tell an epic tale of adventure, sharing the DMing duties, for the better part of two weeks.

Corvis survived and had a son of his own before the year was done, thus the twelfth generation of Fleetwoods had been played and the thirtieth was in the fold.  I can only imagine what the next chapter will hold for the Fleetwoods, but when it does take place, I’ll be sure to list it here for all those who come in to take a look at this long and intricate gaming family tree.

Now you might be wondering what happens as I transition into my 40s and what I believe is called middle-age? Only time can tell, but as long as there is history to write and a family line to foster, all 11 generations of it, then I will endeavor to do so… one Week at a time if I must…

[Note V: I want to say a special thanks to all the artists who contributed to this project. Each piece included here is an original work, and was provided with incredible care. Your talents have always inspired me to keep this ‘thing’ going, to imagine greater than I would have alone, and to believe that my characters deserved more than being simple numbers and letters on a white paper page. To say I’m a fan of what you do is a critical understatement, and I hope this small piece of fan-boy history gives you some glimpse into what you mean to all the fans out there who follow your work like I have over the past thirty years.]