Pinkertons Most Wanted | The Dubby Dubberson Gang

SPECIAL NOTICE TO FIELD AGENTS

The Dubberson Outfit

What began as a loose collection of campfire loafers became a traveling catastrophe stretching from Valentine to Lemoyne. The gang has been blamed — in this entirely fictional parody — for stolen payrolls, missing hogs, suspiciously fast departures, unlawful possession of dramatic hats, and enough chaos to make even an O'Driscoll complain about standards.

PRIORITY APPREHENSION BOARD

Five Entries. One Gang. No Good Decisions.

Ranked by danger, influence, and the amount of paperwork reportedly generated whenever they pass through town.

EXTREME PRIORITY • TWO-MAN ENTRY

The Smith Brothers

Charlie & Chip • “The Lightning Riders”

Known for riding the lightning, hogs, horses, wagons, borrowed bicycles not yet invented, and anything else that gets them from Point A to Point B before the law can organize a posse.

Why they rank #1: the brothers specialize in speed, confusion, synchronized bad ideas, and brazen escapes. One distracts the law while the other somehow makes the situation worse. Witnesses report they have crossed Lemoyne with revolvers out, vanished through Cumberland Forest, and once left Rhodes with three deputies arguing over which direction they had gone.

Danger 10/10Mobility UnreasonableKnown For Fast exits

HIGH PRIORITY

Jake Ambrose

“The Harmless One”

Ambrose looks like a young man who wandered into Valentine to buy fence posts. That is precisely the problem. While louder men draw every eye in the saloon, Jake is allegedly the one checking the back door, counting horses, learning train schedules, and quietly deciding which bridge everyone will be crossing at midnight.

Pinkerton notes describe him as “too normal-looking to ignore.” He has a talent for standing politely near a crime until the crime becomes mysteriously well-organized.

Danger 8/10Cover HarmlessSpecialty Quiet planning

GANG LEADER • HIGH PRIORITY

Christopher “Dubby” Williams

Leader of the Dubby Dubberson Gang

Dubby is the self-appointed center of gravity around which the outfit's plans, feuds, campfire speeches, and unnecessary flourishes revolve. He is charismatic enough to turn a bad idea into a mission and patient enough to explain why everyone else misunderstood the plan after it fails.

Rumor places him from Big Valley to the swamps of Lemoyne, sometimes in suspicious proximity to a mountain lion and almost always wearing more leather than the situation requires. He is said to admire Dutch van der Linde's speeches while preferring the organizational discipline of a man who actually wrote the plan down.

Danger 9/10Role LeaderWeakness Dramatic entrances

MUSCLE • MEDIUM PRIORITY

AJ Monegan

“The Mule”

Monegan is the gang's mule in both job description and spiritual temperament: strong, stubborn, difficult to redirect, and usually carrying something he was not present when the group decided to steal.

No one accuses AJ of overthinking a situation. His function is simpler: lift the crate, hold the horse, block the door, carry the camp, and ask where everybody went five minutes later. Yet Pinkerton agents are warned not to mistake limited strategic interest for limited usefulness — every gang needs somebody who can move the piano.

Danger 6/10Strength Mule-gradeThinking Delegated

ASSOCIATE • WATCH LIST

Little Rye

“The Smallest Man in Camp”

The smallest in every way in the gang: smallest chair, smallest horse allowance, smallest share of the loot, and — according to one irritated deputy — the smallest amount of useful information ever given during questioning.

Little Rye is not considered the most dangerous member, but he has the remarkable habit of being nearby whenever a crime has just occurred. He may not start the trouble, finish the trouble, or fully understand the trouble, but investigators increasingly treat his presence as a reliable sign that trouble is within shouting distance.

Danger 4/10Height Under reviewSpecialty Being there

CASE FILE 77-D

How the Gang Was Formed

The earliest reliable story begins outside Valentine, where the Smith Brothers allegedly arrived separately, left together, and somehow acquired a wagon that neither remembered buying. Dubby Williams met them after what a local stable hand called “a disagreement involving a horse, a lantern, and several interpretations of ownership.”

Jake Ambrose joined next, apparently because somebody in the outfit needed to know where they were going. AJ Monegan was recruited when the gang discovered he could carry twice as much camp equipment as anyone else and ask half as many questions. Little Rye simply appeared at breakfast one morning and, according to surviving camp notes, “never quite left.”

They soon established a moving camp in the style of the Van der Linde gang — canvas tents, coffee that could dissolve a spoon, horses tied everywhere, arguments about money, and one man forever promising that one more score would solve everything.

The fictional Dubby Dubberson Gang gathered at camp — Field photograph marked: “DUBBY DUBBERSON GANG — camp believed north of the Heartlands.”

SELECTED INCIDENTS

Notable Crimes & General Nonsense

SPRING • 1899-ish

The Valentine Telegraph Job

The gang allegedly cut a telegraph line so thoroughly that they accidentally cut their own ability to learn whether the law was coming. The Smith Brothers then escaped west at what witnesses described as “a frankly disrespectful speed.”

EARLY SUMMER

The Cornwall Payroll Decoy

A payroll wagon bearing Leviticus Cornwall's name was diverted by a false road sign, a broken-down cart, and AJ standing in the road looking convincingly confused. No one is certain which part of this was planned.

MIDSUMMER

The Rhodes Hog Heist

Three prize hogs vanished after midnight. Charlie and Chip were later seen moving east at high speed. The gang denies stealing the animals and instead insists the hogs “joined voluntarily.”

LATE SUMMER

The Saint Denis Streetcar Escape

After a card game became “financially complicated,” the outfit allegedly escaped aboard a Saint Denis streetcar. Dubby called it tactical innovation. Jake called it the only vehicle nearby. Little Rye reportedly missed the first car and had to catch the next one.

AUTUMN

The Blackwater Ferry Misunderstanding

Pinkerton records contain six pages of redactions, three contradictory witness statements, and one note reading simply: “Do not let these men near another ferry.” The gang maintains it was nowhere near the Blackwater money and has become suspiciously specific about that point.

ONGOING

The Cumberland Camp Circuit

Agents have found abandoned camps from Horseshoe Overlook country to the edge of Big Valley: spent coffee, playing cards, boot prints, cigar ends, and scraps of maps covered in Jake's handwriting and Dubby's corrections.

LATEST FIELD INTELLIGENCE

Where They Were Last Seen

The most recent credible report places the gang north of Valentine before dawn, breaking camp in a hurry and moving east toward Emerald Ranch. A second witness claims the Smith Brothers peeled south toward Rhodes, while Dubby was overheard saying the outfit should “lie low in Lemoyne,” a sentence that historically precedes them doing the opposite.

Other unconfirmed sightings mention a campfire in Big Valley, a loud argument near Flatneck Station, and Little Rye buying enough cigars in Saint Denis to suggest either a long journey or an extremely ambitious afternoon.

ValentineEmerald RanchRhodesBig ValleySaint DenisBlackwater

FIELD NOTE

“Do not approach the Smith Brothers if mounted, Dubby if speaking, AJ if carrying furniture, Jake if smiling politely, or Little Rye if everyone else has suddenly disappeared.”

— Anonymous Pinkerton field memorandum, authenticity questionable

PUBLIC ASSISTANCE REQUESTED

Have You Seen These Men?

Send the Pinkertons a fictional sighting report. Include the location, which outlaw you saw, and any useful details — especially direction of travel and whether the Smith Brothers had located another inadvisably fast mode of transportation.

WIRE SIGHTINGS TO codyblack845@gmail.com Opens your email app with a pre-filled report.