How to play
The city is up for grabs. Build your crew, claim your corners and pick your fights. Chicago only has room for one winner.
3–5 players total: two to four bosses and Chicago Police. Each side can win.
↓ Download the complete rulebook (PDF, A4)Save it or print it for the table.
1. Make a name for yourself
Be first to 4 Empire Marks, or become the last player standing. A shortage of bank money can also end the game with a final count. Win a completed raid to earn one permanent mark — attacking or defending. An opponent’s withdrawal also counts as your win. Taking an unclaimed business earns no mark.
Run out of money or people and you are eliminated. Your businesses return to the merchants; police seals disappear if police is eliminated.
2. Set up the game
- Choose the Boss count: play with 2, 3 or 4 Bosses. In the digital game, use the Bosses setting. Chicago Police joins every match as an additional player.
- Assign characters and turn order: the digital game shuffles the Boss characters and seats. Bosses take turns in seat order, then Police takes a turn. At a physical table, choose or draw Boss characters and agree who plays first.
- Prepare the board: shuffle the Street Life and Police File decks separately and place all pieces on Start. Every business begins under merchant control.
- Give out starting resources: every Boss gets $12,000 and 50 soldiers; Police gets $12,000 and 28 officers. Each Boss also gets one Contacts card. Keep the rest in the supply.
No one begins with an active superpower. Standing on Start at setup gives no income, power roll or police encounter.
Cash and banknotes
For a physical game, prepare 420 banknotes worth $265,000. Give each Boss and Police the same $12,000 starting bundle: 1×$5,000, 5×$1,000, 3×$500 and 5×$100. With four Bosses and Police, the bank begins with $205,000 after setup.
Banknote supply for the physical game| Value | In the box | In each starting bundle |
|---|
| $5,000 | 20 | 1 |
|---|
| $1,000 | 100 | 5 |
|---|
| $500 | 100 | 3 |
|---|
| $100 | 100 | 5 |
|---|
| $50 | 100 | 0 |
|---|
| Total | 420 | 14 |
|---|
The $50 notes make exact change for the Fixer’s half-price bribes and other $50 increments. A banker may play, but must keep the bank’s money separate. Players may exchange notes of equal value with the bank at any time. In the digital game, open Banknotes beside a player or Police to see their notes; the Ledger shows the bank’s remaining supply.
If the bank cannot cover a required payout with its total remaining money: pay what it can and record the rest as bank credit in $50 increments. Count that credit as the recipient’s cash, then end the game immediately. A shortage of one note value alone does not end the game; exchange notes first.
Bank shortage final count: each remaining Boss and Police scores $10,000 per Empire Mark + cash (including bank credit) + the listed establishment costs of their controlled or secured businesses + $100 per remaining soldier or officer. Highest total wins. Break ties by more Marks, then more cash, then more people, then earlier Boss seat; Police is last in seat order. Eliminated sides cannot win.
3. Make your move
- Roll two dice and move. Bosses travel clockwise. Police travels counterclockwise after the Bosses. Doubles give no extra turn.
- Resolve your destination. Start uses its special rule. If the police pawn is there, choose the bribe or raid the police; this has priority over any business. Otherwise, if another side controls the business, choose to pay or raid. Card movement also resolves the new destination.
- Take one available action. Take control, recruit, raid, trade at Start, rebuild contacts if your cash is below $1,500, or pass.
Moving forward onto or past Start pays $4000 and gives the moving boss a Superpower roll. This applies even when the final space is beyond Start, not only when the piece stops on Start. Businesses give no extra Start income. The opening setup gives no ordinary Start reward. Big Boss Meeting gives no ordinary Start payment, but its participants still roll for Superpower if the meeting continues.
4. Own the street
Pay the establishment cost to take a merchant’s business. When another side controls the business, the arriving side chooses either to pay its Protection or Inspection fine, or to raid. The blue police seal controls a police business even when the police piece is elsewhere. If the police pawn is also there, the police encounter has priority: choose the bribe or raid the police instead, with no second business payment.
Protection and Inspection fines start at $500 and rise $250 per block clockwise. Control a whole block and its payments double. A payment ends the encounter. A raid also ends the encounter; a failed raid does not create a second payment.
At a recruitment hub, buy 4 people for $1500 or 10 for $3000, up to 120 total. Police pays the same recruitment prices.
5. When talking stops, roll the dice
In a raid, both sides roll one die. The lower roll loses one person. A tie causes no loss: roll again, unless an active power changes it.
- Lose 20 people and you lose the raid.
- After losing at least 10, you may withdraw and concede the raid.
- A defeated defender loses the business. A defeated attacker fails to take it.
- The winner earns one Empire Mark. Lose your last person and you are out of the match.
- Both payment and raid resolve the encounter once. A failed raid does not trigger another payment or another raid on that landing.
6. The law wants its cut
Outside Start, if a boss and the police pawn share a space, the police encounter has priority over the business. If several bosses are there, each faces one encounter. Each boss chooses the bribe or a raid against the police.
Accept: commit first, then roll one die. Pay $100 per pip to police. If you cannot pay, you are eliminated. Payment ends that encounter.
Contacts cards are not required or spent for bribes in this edition.
Raid: the same raid rules apply against the police officers. A successful defender or attacker earns the Empire Mark; the business changes control only when it is part of that encounter.
Police never draws Street Life or Police File cards. Start remains the exception.
7. Start: a deal, or a disaster
Arrive at Start with another free boss already there and you may trade businesses and optional cash, if both agree. Trading is optional.
If an arrival brings police and bosses together at Start, every boss there is immediately eliminated. No bribe or power can save them. Bosses elsewhere or in Detention survive. One surviving boss wins; two or more continue. If none survive, police wins.
Big Boss Meeting sends every free boss to Start, without ordinary Start income. Detained bosses stay away. The same police raid rule applies.
8. A cell is no place for business
Landing on Detention normally is just a visit. Being sent there detains you: on your next turn, skip movement, collect $500 and return to play with an action. While detained, you cannot trade or take part in police encounters or meetings.
9. Play your strength
Whenever normal movement reaches or passes Start, roll for your superpower: 4–6 activates or keeps it; 1–3 removes it. It lasts until the next Start renewal. Read your character’s power card. An existing Don or Street Bat bonus resolves before renewal. The $4000 Start payment and this roll happen on the same passage. Big Boss Meeting skips the ordinary Start payment, but its participants still roll for Superpower if the meeting continues.
Powered Night Gun wins defensive ties. Active police Warrant wins attacking ties. If they face each other with both powers active, ties reroll.
Keep enough cash to survive the next corner. Keep enough people to defend it.
Details & special situations
Know the people at the table
These abilities apply only while the character’s power card is active. Nobody starts with an active card.
- The Don
- While powered: roll a die for $500 per pip when reaching or passing Start.
- Queen Bee
- While powered: personal and business police inspections are cancelled.
- Iron Fist
- While powered: gain exactly 50% more soldiers from every positive soldier source.
- Lucky Jack
- While powered: receive $500 from each other boss you meet on your space.
- Street Bat
- While powered: roll a die for soldiers when reaching or passing Start.
- Night Gun
- While powered: win tied dice when defending a raid.
- The Fixer
- While powered: pay half the rolled bribe.
- Velvet Boss
- While powered: gain five soldiers when taking control from a boss, two from a merchant.
- Chicago Police · Warrant
- While active, win tied dice when attacking. Against a powered Night Gun defending, tied dice reroll.
Iron Fist pays the normal recruitment price and receives 6 instead of 4, or 15 instead of 10. His raid casualty limit remains 20. Queen Bee’s protection never prevents a Start raid.
The street does not stop for a card
A card that moves someone also resolves where they land. Payments, encounters and card spaces still apply. Moved police can inspect, secure a business or recruit at a hub; police never draws either deck. Follow the card’s instructions about Start income.
Heist: collect $1500 and move police three spaces counterclockwise. Arrested: go to Detention. A normal visit to Detention still allows police encounters; a detained boss is excluded.
Deals at Start
One arriving boss and one waiting boss are enough for a meeting. Exchange one or two businesses and optional cash, with both parties’ agreement. An accepted trade uses your action. Rejection moves nothing and leaves other actions available, but you cannot make another proposal that turn.
At Big Boss Meeting, free bosses attend in seat order, starting with the card’s drawer. Each may offer a trade or pass. The drawer then resumes their normal action without another proposal. Detained bosses do not attend. If police is present, the Start raid takes priority.
When things go wrong
Marks are permanent: they cannot be traded or stolen. Cards, trades and taking merchant-run businesses give no marks. Each landing has at most one pay-or-raid encounter. If a payment leaves you at $0, you are eliminated. An unaffordable committed bribe also eliminates you.
If the police pawn is present, the police bribe-or-raid encounter takes priority over a business encounter. On Start, use the special elimination rule instead.
Card reference
Find the card’s title below. Repeated copies share the same entry.
Street Life
- Contacts
- A name in the right precinct still opens doors. Keep this Contacts card, maximum two. Contacts are not spent for bribes and do not block Police File cards. If you already hold two, discard this card.
- Big Boss Meeting!
- All free bosses must attend: move directly to Start. Detained bosses stay in Detention and do not participate. No normal Start income. If police is at Start, every boss at Start is immediately eliminated and their businesses return to merchants. If no boss remains, police wins. If exactly one boss remains elsewhere or in Detention, that boss wins. If two or more remain, the match continues. No bribe or power can prevent the Start raid. Otherwise, each participant may propose one trade or pass in seat order, starting with you. Both parties must agree. Then resume your normal action.
- Back-alley recruits
- Two neighborhood soldiers join you. Gain two soldiers. Move police 3 spaces counterclockwise.
- A rival turns coat
- Two soldiers change allegiance. Recruit two soldiers and pay $500 for the introduction.
- Bootleg payoff
- A hidden whiskey shipment pays handsomely. Collect $1500 from the bank.
- Protection squeeze
- Lean on the wealthiest rival. Collect up to $500 from that rival. Move police 3 spaces counterclockwise.
- Service-alley entrance
- Slip through the back way. Advance to the nearest merchant-run business. You may take control by paying its establishment cost.
- A whisper at the precinct
- A friendly word redirects the beat. Move police 2 spaces clockwise.
- Hijacked whiskey truck
- The cargo disappears before reaching the warehouse. Collect $1000 from the bank.
- Neighborhood loyalists
- Two loyal soldiers answer the call. Recruit two soldiers.
- Medicinal whiskey permit
- A useful paper trail revives an old connection. Recover one used Contacts card from the Street Life discard, if available and you hold fewer than two. Otherwise nothing happens.
- Speakeasy receipts
- The night crowd pays well. Collect $500 per Nightlife business, or $500 if you control none.
- Lakefront shipment
- A boat reaches the harbour before dawn. Collect $500 per Harbour business, or $500 if you control none.
- Rival speakeasies
- Two rooms were promised the same liquor. Lose $500 and move police 3 spaces counterclockwise.
- Ward connection
- An old ward captain clears the road. Advance three spaces. Resolve your destination.
- Getaway through the alley
- Lose the tail by doubling back. Move back two spaces. Resolve your destination.
- Cooked ledgers
- The books survive a quick inspection. Collect $500 and move police 2 spaces clockwise.
- Champagne tower
- The club celebrates past closing time. Pay the bank $800.
- Neighborhood respect
- The street backs an underdog. Recruit two soldiers if you have fewer than three; otherwise collect $500.
- Supper-club receipts
- Every late table adds to the take. Collect $500 per Dining business, or $500 if you control none.
- Front-page legend
- Your name fills the evening papers. Collect $1500 and move police 3 spaces counterclockwise.
- Informant at large
- A witness points the law in your direction. Move police 4 spaces clockwise.
- Gangland truce
- The city goes quiet for one turn. Businesses you control cannot be raided until your next turn ends.
- New territory
- Fresh muscle has a price. Recruit two soldiers and pay $500.
- Backroom poker
- One hand decides the take. Roll one die. Collect $200 times the result.
- Front-page scandal
- The morning edition names names. Pay $800 and move police 3 spaces counterclockwise.
Police File
- Prohibition raid
- Dry agents smash the stockroom. Pay $1500 and move police 3 spaces counterclockwise.
- Tail surveillance
- Plainclothes officers follow at a distance. Move police 3 spaces counterclockwise.
- Commissioner on the payroll
- The arrangement is costly. Pay $500. Move police 4 spaces clockwise.
- Grand-jury witness
- A sworn statement puts the law on your trail. Move police 6 spaces counterclockwise.
- Thin evidence
- The file fails to hold together. Move police 2 spaces clockwise.
- Court injunction
- A judge returns one address to lawful hands. Return your highest-cost controlled business to its merchant. No compensation. If you control none, nothing happens.
- Dry agent inside
- A federal informant reaches your books. Pay $1000.
- Station-house questions
- The interview lasts until morning. Pay $1000.
- Bad tip
- The address is wrong, but the delay is real. Visit Detention. Do not collect Start income.
- Treasury audit
- Tax investigators inspect every ledger. Pay ten percent of your cash, rounded up to $100.
- Telephone tap
- A careless call costs you. Pay $500 and move police 3 spaces counterclockwise.
- Prohibition squad
- The dry squad arrives at your door. Move police directly to your space and resolve a police encounter. Accept the rolled bribe or refuse and face an inspection.
- Clean ledger
- The numbers give them nothing. Move police 2 spaces clockwise.
- Alley patrol
- A patrol catches the handoff. Pay $700.
- Defense attorney
- A courtroom favour revives an old connection. Recover one used Contacts card from the Street Life discard, if available and you hold fewer than two. Otherwise nothing happens.
- Friendly judge
- The warrant loses its force. Move police 4 spaces clockwise.
- Federal seizure
- Agents seize an address or levy a fine. Return your highest-cost controlled business to its merchant without compensation. If you control none, pay up to $2000.
- Caught with the goods
- The crates are open when the law arrives. Go to Detention. Your next turn is a recovery turn.
- Missing ledgers
- The tax men notice a gap. Pay $1500 if you control a Downtown business; otherwise pay $500.
- Precinct informant
- Someone inside gives up a name. Lose one soldier and move police 3 spaces counterclockwise.
- Paddy wagon
- The wagon blocks the avenue. Move back two spaces. Resolve your destination.
- County jail
- The cell door closes. Go to Detention. Your next turn is a recovery turn.
- Bail money
- Freedom has a price. Pay $500 and move police 2 spaces clockwise.
- Trail goes cold
- The detectives lose the scent. Move police 4 spaces clockwise.
© 2026 Pablo Fernandez Terra. All rights reserved.