The Deckmasters Organization in Skydwellers | World Anvil
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The Deckmasters

Stretching beneath the resident portion of the Sky Cities is a bustling network of shops, farms, malls, stores, parks, groves, fields, libraries, factories, offices and markets that form the work sector of the Cities. Wide streets big enough for three full-grown dragons to walk through, and cavernous buildings grown from enormous trees. Some of the less populated streets would be lined with warehouses, research centers, guild halls, and weather stations. The streets would be crowded with shoppers, people on their daily business, families on outings, and even runners. Sections of buildings or even entire stores will occasionally be open to the air, covered only by a single woven roof, adding to the chaotic, bustling look.   This tangled web of daily interactions provides the perfect opportunity for a thief - daily pickpockets, nightly robberies. Swindles, scams, embezzlements, half-hearted deals - all part of a thief's trade. Most thieves are solitary - simple pickpockets, or nightly robbers. But the largest and most covert organization of all is that of the Deckmasters.  
Design on the back of all Deckmaster cards

Founded by a former powder lord, the Deckmasters began as a small band of thieves, composed mainly of powder addicts looking to fund their now extremely expensive addiction. Over the years, it grew, even during the chaos of the Draconic Invasion. What started out as a small thieving operation led to full-blown schemes and scams, and the name of Deckmaster became intertwined with almost all business dealings in the sky - though not many knew that.

Such a ruthless organization is feared by most everyone - any knock on the door at night by a runner bearing the emerald wings sends chills into the boots of the shop's owner, and even policemen secretly fear the Deckmaster Aces. Most of the time, it's a fear that lies buried under the surface, but every time a theft or incident is reported, the public backlash has even the organization's members on edge.

Structure

Keeping with their name, the Deckmasters organize themselves by the names of cards. They're ranked by gemstone - starting at onyx, the lowest, then sapphire, diamond, ruby, and emerald. The gemstone ranks denote experience and value of a member, with onyx being relatively inexperienced and emerald being highly praised.   Aside from the jewel ranks are the card ranks - starting at seven, then going from jack, queen, ace, then king. Sevens are the main members, and the most populous. Queens are the commanding officers, in charge of instructing the sevens. Aces and jacks, rather than holding a leadership rank, refer to the purpose they serve - jacks of all trades, who can serve well in a variety of missions, and aces, highly specialized personnel mostly known for their fighting abilities. And the kings, of course, are the ones in high command - the big guys, the ultimate leaders.   Of course, among the sevens, there are different classes that take care of different jobs. There are:
  • Runners: bring messages between bands and deliver threats to any clients of the Deckmasters.
  • Pickpockets: work primarily in the day on crowded streets
  • Raiders: rob homes and businesses during the night
  • Marauders: pull off big thefts - museums, warehouses, mansions, etc.
  • Swindlers: are a part of larger schemes, scams, and general embezzlements

Deckmasters will keep their ranks sewn just under their inside collar, in the color of their jewel rank and different symbols based on their classes - wings for the runners, coins for the pickpockets, differently ornate crowns for the kings and queens, and so on. They keep this carefully patched up lest they be identified as a thief and locked away for life. They'll be organized into bands with different numbers of classes, headed by queens and overseen by the kings.  

Culture

"Cut the cards, Phil, and let's see who's got to go run out tonight."   "I was under the impression that you enjoyed runs."   "No more than I enjoy playing a game of Winds with everyone, knowing that I don't have to risk my rank tonight."   "Okay, I'll cut the cards. Vincent, you're up. On your way out, tell Mr. Queenie that the falcon's dropped the coin. Can you do that for me? Thanks. Good luck - you'll be stopping by the merchant's guild tonight."
Although there are relatively few Deckmasters in all - just three separate bands in total - they keep their identities hidden from each other between bands. As they're highly sought by the police force, theirs is a society of secrets, pass phrases, coded messages, key words, and phony coins. Their losses early on led to a series of strict training and ruthlessness even among members. Though bands often have a kinship with each other and decide their own code of morals, they are thieves - no honor, no sense of duty. If a Deckmaster were ever to be caught and arrested, they would be on their own, and banned from any further heists.   Of course, many members live for the risk. The chance to prove themselves, to rise the ranks, to find close friends and cohorts within their bands, and the constant adrenaline rush. Deckmasters devote themselves almost entirely to their work, and as a result, often have strained relationships with their Bonds - there are no fully-fledged Deckmaster dragons. The lack of opposable thumbs and pride that places them above petty theft is a general discouragement from that.  
Type
Guild, Thieves
Parent Organization

Headquarters

Thanks to the recent membership of Ashley Lywin, the Deckmasters have found an unofficial base of operations in the Coin Vault. There's a small room on the uppermost level where they keep all their records hidden in the walls and floor - membership records, client documents, profit ledgers, and more. It's also a safe haven for any Deckmaster in trouble, and the place to go to find both plenty of open pockets and at least one Queen prepared with instructions.   Of course, the owners of the inn would be mortified to find out that they're unintentionally aiding the Deckmasters, so they find ways to keep their minds at ease - bringing in customers with magic shows to discourage the owners from asking too many questions, having a few key members sit down weekly with the owners to develop a good relationship with them, and having a strict code to maintain a cordial and amiable presence within a twenty-span radius of the building.
Crowd at a festival (prime pickings for a seasoned Deckmaster)

Prominent Thefts
Due to a string of recent successes, the Deckmasters have gotten even bolder with their robberies, pulling more and more elaborate schemes. These include the raiding of Governor Gyrot's mansion, the deal they managed to cut with the merchant's guild, and even the brazenly obvious pickpockets going around during the Midwinter Festival.   But perhaps the most famous of all was the recent brawl that was started by the Aces who had been sneaking in and stealing metal from the  Swordsmen's League. When apprentices of the guild had snuck into their building to practice for their Midwinter Festival display, they saw a team of five Aces plundering the precious metal speartips and Edges from their cases. Most would back down, but the apprentices threw themselves at the Aces, and the ensuing fight ended in one captured Ace, two hospitalized apprentices, and many nervous Deckmasters.  
In light of this loss, the Kings are recalculating their policies on secrecy and how far they are willing to go to make a profit. To top it all off, a simultaneous (and partially to serve as just a diversion) chain of robberies in the marketplace shops resulted in the arrest of talented Jack Ashley Lywin. These two skilled Deckmasters have since escaped custody, but, courtesy of Deckmaster policy, are no longer members of the thieving guild.

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