ChicagoShadows
Where the City Is Headed

The road ahead.

A continuous world is never finished. Here's what's being built, what's planned, and what's already on the streets.

🗓️ Planned 5

Planned high impact

Capo Territories

Capos get defined turf so weekly collections, patrols, and local errands default to their area - cutting micromanagement and keeping your empire humming without constant oversight.
  • Assign exclusive blocks to a Capo; transfers first clear the previous owner (GoC-style exclusivity).
  • Auto-route collecting and patrol inside the assigned turf; allow manual overrides.
  • Map overlay with Capo colors, loyalty-band/heat hovers, and a quick “Transfer Area” tool.
  • Consider the Capos Stats, Skills to impact the efficiency, honesty, morale loyalty of Capo and assigned crew.
Details →
Planned high impact

Prohibition Supply Chain - Brew, Smuggle, Serve

The booze business comes alive. Build hidden stills, breweries, or distilleries to produce moonshine, beer, or whiskey. Store it in your warehouse. Supply your speakeasies. No supply means no income - and destroying a r…
  • Build production facilities by converting owned businesses - a bakery hides a still, a warehouse becomes a brewery.
  • Three product tiers: Moonshine (cheap, low value), Beer (medium), Whiskey (premium) - each with different production costs and speakeasy revenue.
  • Speakeasy income now depends on supply: empty bar earns nothing, moonshine gets base rate, whiskey doubles it.
  • Production facilities can be targeted by rivals - Sabotage, Robbery, and Assault orders destroy or seize your output.
Details →
Planned medium impact

The Gazette House - Shaping Public Opinion & Planting Stories

A new city landmark gives crews a discreet way into the press business. Players can sway public opinion, commission “favorable coverage,” or leak machine-generated stories convincing enough to mislead rivals.
  • Add the Gazette House as an interactive city building with unlockable influence tiers.
  • Let players publish boosted reputation pieces, smear campaigns, or subtle narrative nudges tied to diplomacy and heat.
  • Introduce artificial-looking articles that mimic system-generated news, enabling misdirection that even human players may interpret as genuine.
Details →
Planned medium impact

Active Recruiting - Send Crews to Find New Talent

Instead of waiting for gangsters to show up on their own, you'll be able to send a crew out to actively recruit new members for your family - just like a real 1920s boss would.
  • Assign a crew to a new "Recruit" order to actively search for potential hires
  • Find more or better recruits based on your crew's skills like Negotiation and Street Smarts
  • Recruits appear in your Fresh Meat panel - you still choose who to hire and pay their salary
  • Balance a real tradeoff: spend crew time growing your family or running profitable operations
Details →
Planned medium impact

Pick the Right Gangster for the Job (Enhancement Report #257)

Soon you'll be able to assign specific gangsters to a job based on their skills, so your smooth talker handles extortion while your bruiser handles the robbery.
  • Choose which gangsters in a crew handle each job, not just how many
  • See each gangster's relevant skills when assigning them to an order
  • Send your best negotiator to run a business, your toughest to collect debts
  • Keep a smart auto-pick default so new bosses aren't overwhelmed
Details →

✅ Shipped 8

Shipped high impact

AI Market Interaction & Catch-Up Buying System

First released in the game's round-based era — since adapted for the new continuous city. The current Alley Market logic creates a fairness issue: AI factions buy during round processing, while humans buy afterward. Be…
  • Introduce a catch-up mechanic: determine buying priority by player score, so the weakest ai faction always buys first.
  • The market consistently offers 10 items; after each AI finishes buying, the market immediately refills back to 10.
  • Items remain available for 2-5 rounds before rotating out.
  • The human player buys last in the sequence.
Details →
Shipped medium impact

Crew Payroll Risk Warnings

First released in the game's round-based era — since adapted for the new continuous city. Players now get early warnings when their cash reserves can’t cover upcoming crew salaries. This system exposes looming financia…
  • Add dynamic yellow warning when cash fails to cover the next 3 weeks of salaries but still covers 1 week.
  • Add red critical warning when cash is not enough for even one week of crew payroll.
  • Update warnings automatically each round so players always see their real financial risk in News → Board.
Details →
Shipped high impact

Smuggle Ware & Robbery Loot Flow

First released in the game's round-based era — since adapted for the new continuous city. In the shadows of 1920s Chicago, a robbery is no longer where the story ends - it’s where the real business begins. Crews can ha…
  • Itemized Loot & Stock-Driven Heists: Robberies now pull real shop inventory - jewelry, electronics, antiques - using dynamic stock tables that fluctuate over time.
  • Warehouse Logistics & Auto-Routing: Owned warehouses automatically receive stolen goods, track capacity and risk, and support distribution into owned shops for income boosts.
  • Smuggling & Fencing Economy: Players can run smuggle orders to clear warehouses for cash, influenced by city-wide demand pulses, heat, and cooldowns.
  • Risk & Counterplay Hooks: High-value stock attracts raids, rival hits, and police pressure, creating new strategic choices around timing, storage, and security.
Details →
Shipped high impact

Smoother First Steps

First released in the game's round-based era — since adapted for the new continuous city. Chicago is already deep. This step makes sure new bosses don’t get lost in the fog. We’re sharpening menus, improving guidance, …
  • Clearer menus and navigation: Reducing visual noise and sharpening labels, hierarchy, and layout so players can immediately see what matters in the current round. The intent is not to hide systems, but to surface what is relevant now, making early decisions feel readable and intentional rather than overwhelming.
  • Tooltips as quiet, just-in-time guides: Expanding contextual tooltips across orders, stats, and menus so explanations appear only when they answer an active player question. These tooltips act as optional scaffolding, especially for first-time players, without interrupting play or forcing a linear tutorial.
  • A Tutorial City as a parallel entry point: Introducing a dedicated tutorial city or starter environment that exists as a parallel game instance, not a mandatory tutorial. Within this space, systems unlock gradually over the first rounds, supported by light quest guidance and narrative framing. Players can choose this low-pressure, guided environment or start directly in a full city. Both paths coexist without penalty.
  • One-click playstyles with optional depth: Providing high-level, one-click actions for common early tasks such as exploring, collecting income, or applying pressure. Behind the scenes, the game makes reasonable default decisions. At any point, players can opt into deeper control, fine-tuning crews, targets, timing, and execution. This allows different playstyles to coexist from the very beginning: hands-on optimizers and high-level decision-makers.
Details →
Shipped medium impact

Boss Handbook & In-Game Tooltips

First released in the game's round-based era — since adapted for the new continuous city. Every number, label, and mechanic in the game is getting a hover tooltip that explains what it means and what you should do abou…
  • Hover any dotted-underlined term to see a plain-language explanation of that specific mechanic
  • Rich popups answer 'what does THIS number mean and what do I do about it' instead of generic definitions
  • Open the Boss Handbook from any screen to browse the full reference without leaving your game
  • Every screen audited one at a time: News, City Map, Crews, Locker, Fleet, Orders, Alley, Contacts, and more
Details →
Shipped medium impact

Diplomacy-aware combat

First released in the game's round-based era — since adapted for the new continuous city. Deepen the city’s politics with true Neutral, Peace states - turning every encounter into a test of loyalty, restraint, and timi…
  • Expand diplomacy tiers beyond War to include Neutral, Peace relationships.
  • Reflect these states directly in combat logic - Peace allows debates or warnings.
  • Audit all engagement triggers so diplomacy status dictates whether conflicts even start.
  • Highlight current relations in previews, summaries, and the diplomacy board for clarity.
Details →
Shipped medium impact

Newsreel round opener

First released in the game's round-based era — since adapted for the new continuous city. Kick off each round with a front-page vignette - last week’s biggest shakeups distilled into punchy headlines and quick jumps.
  • Auto-generate headline + subhead from key events (wars, boss falls, turf flips, rare drops).
  • Include call-to-action links that deep-link into the right panels (conflicts, diplomacy, board, market).
  • Keep it skippable with a single key/btn; remember preference for power users.
  • Prioritize stories by impact and uniqueness; collapse minor items into a “More” rail.
Details →
Shipped high impact

Boss death empire collapse

First released in the game's round-based era — since adapted for the new continuous city. When a boss dies, their entire empire crumbles - crews scatter, rackets go dark, and the streets whisper the fall.
  • Auto-disband all crews tied to the fallen boss; release controlled territory and neutralize linked businesses.
  • Cancel outstanding orders, conflicts, and alliances for the defunct family.
  • Trigger dynamic news events, board updates, and city-wide AI rebalancing to reflect the power vacuum.
  • Redistribute abandoned gangsters and rackets to nearby factions over time.
Details →
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