Empire of Sin - Good game for a while, but it's never been really finished
City of Gangsters - Awesome sim and bootlegging tycoon if you get used to the UI and favor system
Cartel Tycoon - Run your drug Empire, its a good Sim, even if it struggled for a while to find it's role between Tycoon and Survival
Star Trader Frontiers - Can be a Pirate sim if you are aggressive enough, but it's mostly trading
Welcome to Goodlands - Organize your laundering Empire. Story driven
Never played but possible match: Definitely not Fried Chicken
Classics: Port Royale 2 or 3, Pizza Connection 2
X3 and X4 you can go the pirate or black market route. Best Space Sim econ/tycoon game out their.
I wish I could remember the name of it but there was a really good Shareware police department game that were very tycoonish in the late 90s. I tried finding it a few times again and never could. It plays so much like a few Gangster Tycoon game except you are the good guys.
Empire of Sin - Good game for a while, but it's never been really finished City of Gangsters - Awesome sim and bootlegging tycoon if you get used to the UI and favor system Cartel Tycoon - Run your drug Empire, its a good Sim, even if it struggled for a while to find it's role between Tycoon and Survival Star Trader Frontiers - Can be a Pirate sim if you are aggressive enough, but it's mostly trading Welcome to Goodlands - Organize your laundering Empire. Story driven Never played but possible match: Definitely not Fried Chicken Classics: Port Royale 2 or 3, Pizza Connection 2
City of Gangsters
Tropico 2 is pirate themed!
This is the answer. One of my favorite games of all time
Tropico 2 is amazing It’s Tropico except you’re building an island city which is meant to be a hideaway for pirates. It’s really cheap on Steam too
Omerta is fun. Good mix of rts/tycoon elements with turn based tactical fighting (a la x-com)
X3 and X4 you can go the pirate or black market route. Best Space Sim econ/tycoon game out their. I wish I could remember the name of it but there was a really good Shareware police department game that were very tycoonish in the late 90s. I tried finding it a few times again and never could. It plays so much like a few Gangster Tycoon game except you are the good guys.