Have You Played… Gangsters: Organized Crime?

Have You Played? is an endless stream of game retrospectives. One a day, every day of the year, perhaps for all time.

When I first played Gangsters: Organized Crime [Wikipedia page] in the late 90s I didn’t really play strategy games. This one predated The Sopranos, so my grasp of epic gangster stories stemmed from Scarface, Once Upon A Time in America and The Godfather trilogy – all of which weaved deep and intricate tales over the course of just a few hours.

Gangsters: Organized Crime taught me that out you can’t assassinate a mayor on your first day on the job.

Which is why my first venture into the world of virtual organised crime was unsuccessful. After just minutes of assuming the hotseat I sent budget bandit Gabrielle ‘Joker’ Bekos to city hall where he immediately botched his first job. By taking down the mayor, I’d planned to take control of the city, yet instead Bekos’ legacy was a white chalk outline on Main Street. Perhaps my henchman’s nickname was telling, and I quickly learned that ruling the streets of New Temperance would require patience and perseverance.

I hired gangs of hoods, set up protection rackets, extorted local businesses and grew my territory into an empire. In Gangsters, success is hinged on one of four outcomes: going clean, becoming mayor yourself, forming an alliance with rival gangs, or wiping out the competition entirely. The latter, as you’d probably imagine, is the most satisfying and I never once kicked off a game without a leg-up from the I LOVE HANSON money cheat because I’m straight up gangster 4 life.

Gangsters: Organized Crime now lives on GOG which means you can avenge Beko’s death for just a few quid.


  1. Stonehead says:

    That was a great game. I was hoping Omerta would become its spiritual successor, but luck wasn’t on my side. There is no game that makes building a criminal empire as fun and engaging as this one.

  2. Secatus says:

    Unfortunately this game won’t run on any OS newer than Windows 7 :(

    • Horg says:

      According to the GoG forums, you can use the Microsoft Application Compatibility Toolkit to crate a modern OS fix using ”force direct draw emulation”. I’ve not used it for Gangsters but I know that fix works for the disc versions of some old games like Baldur’s Gate, which has bugged fog of war and some sprites which load as a black box without the fix.

  3. dongsweep says:

    Oh God, the “I Love Hanson” cheat – that just brought back some memories!

    This was a great game, I always hoped a proper sequel would come. Luckily, Mafia 3 is coming out this week but that will likely only give a taste of the fun that could be had with Gangsters.

    This game made me think this is what “Sim Mafia” would look like back then if the Sim people had made one.

    • Jerppa says:

      “I always hoped a proper sequel would come.”

      Gangsters 2: Vendetta was released in 2001.

      • RaveTurned says:

        Let the record reflect that we observed the release of Gangsters 2 all those years ago, and we are still wondering if and when a proper sequel will ever be released.

  4. ThePuzzler says:

    I played this a few times, but it got less fun when (mechanical-spoiler warning) I realised it was a very bad idea to give any of my mobsters guns. When rival gang members saw one another in the street, generally they would start blazing away at one another with firearms, and then the police would arrive, and your man would wind up dead, arrested, or wanted. All of these results were bad for you. If you didn’t hand out guns, the rival mobsters would open fire and your guy would run away. He had a good chance of escaping, and the police had a very high chance of taking down the killer, and your reputation stayed clean.

    • DeadCanDance says:

      The way I remember gunfights hapenned only if your men were near the enemy hq or if you ordered them to. Generally they would just tell you they saw someone from another gang.

  5. rustybroomhandle says:

    I think someone should attempt a modern spin on Mugsy from Melbourne House. Such stylin’ graphics.

  6. DeadCanDance says:

    This game brings me such good memories. Blowing up the enemy’s hq, robbing banks and setting up legal business to laundry up the dirty money you made, the tension from seeing groups of people carrying guitar cases… good times.

  7. mrvega says:

    Perhaps my absolute favourite game of my youth. It taught me the word ‘tenement’, used to run just fine on my old Pentium 90Mhz, and it was the first game I ever bought from GoG some 10 years later.

    I’d hoped Omerta would be a decent successor but it was awful and couldn’t replicate the planning aspect that Gangsters had.

    I could never manage to get very ‘far’ in the game, but still loved every second. The sequel was pretty meh.

    “I can only do this much”

  8. Sin Vega says:

    Coincidoobily, I’d just started poking around with this again for reasons. It’s another of those settings that surprisingly few games go for.

  9. Horg says:

    I had this one when I was still fairly young, and while I liked the aesthetic and management mechanics, I really got stuck on the prohibition era gangster jargon. It’s not easy being a mob boss if you don’t know what a ”speakeasy” is, or where exactly the best place to run a ”numbers racket” might be. The worst part was, despite the manual being old school novel sized, non of the gangster terminology was explained. I’d like to go back to Gangsters, now I have a better understanding of the time period, there really isn’t much else like it.

    • Sin Vega says:

      It’s not easy being a mob boss if you don’t know what a ”speakeasy” is, or where exactly the best place to run a ”numbers racket” might be.

      I want to watch this tv series.

  10. Doubler says:

    I remember all my games rapidly devolved into an all-out war between myself, rival gangs and the cops pretty much the moment our paths crossed. Fun to watch, but I was never quite sure how to stop that from happening.

    I vaguely remember winning at one point by literally blowing up city hall and getting elected mayor after murdering the more popular candidates. Clearly I would make a great politician.

  11. NephilimNexus says:

    This game had a great concept and plenty of good systems that would make it fun even today if it were not for two things:

    1) Time compression borked pawn movements so that they only got half as much done per week as they would if you just left it on x1 speed and watched a movie in another window.

    2) Once an AI player found your HQ they would just spam zerg rush it every week with everything they had until one guy managed to slip past your guards and murder your avatar. Pretty much 90% of my games ended this way. The problem was that you were limited to five goons guarding your building and five more patrolling outside, so ten goons max. If the enemy rushed you with twenty (and I’ve seen far more than that, as there was no limit to identical attack missions) then there was literally no way to keep from losing.

    Sadly, Gansters2 decided it wanted to be linear story game instead of strategy game and bombed as badly as it deserved. And therein has been the problem with every mafioso game ever since the original gangsters: They all want to be story games, and story games always end up on rails. And strategic aspects that slip in are just time sinks; artificial hurdles to drag out game play between story chapters. You aren’t playing the strategic part to win, rather you’re just trying to “level up” the main character so you can do the next story mission.

    It’s boring. Gangsters had no story, no rails, no constraints. It was doing “emergent gameplay” before it was a pointless buzzword. The story was entirely up to the player to create. Sadly, too many prima donna story writers in the industry now to ever go back to this classic style of open-ended mobster gameplay.

  12. Kohlrabi says:

    I get wet dreams imagining what Paradox might cook up for the genre of gangster strategy.

  13. Esin12 says:

    Never played the first one, but got really into the second for a while. I was recently thinking about grabbing it on GOG but then I remembered all of the frustrating old-schooly mechanics and decided against it. Still waiting for a proper contemporary gangster sim/management game…

  14. W4nT4n says:

    Ah, such good memories. I never won a single game, only played against the AI. Could never figure out, why the opponents could scare all citizen to pay them yet I couldn’t win them back. Also once your HQ was found, you would never be able to survive the next week =/

  15. DKATyler says:

    Seems like the right place to ask:
    I’ve been hunting for a similar game to this for the last dozen years (or longer?) after playing a demo and forgetting the name.

    Very much the same style but acquiring businesses was by “intimidation”, your mobster walked up to the door and started beating on it with a club. Sometimes the business would say “Alright Alright I’ll pay” and you could upgrade it with illegal businesses then. Other times the business would call the cops. And odds were good if your mobster didn’t get lost before the cops drove up, well arrested was the usual outcome.

    Oddly the mission select screen with a half-dozen stacked gold coins next to each one was also memorable.

    • ThePuzzler says:

      There was a game called Gangland about 12 years ago, don’t know if that was it?

    • rabbit says:

      i’ve never found anything like gangsters. such a great (albeit very flawed) game.