Insane Monopoly is a board game that was never supposed to break containment. As an extension of Ultimate Monopoly, which already made the classic board game twice as complex, the labyrinthian game was originally confined to Tabletop Simulator. That all changed in 2025, though, when the designers of Insane Monopoly (and its expansion) decided to test the spin-off in-person.
It took them nine hours. They didn't even finish the game.
Downin, one of the developers for Insane Monopoly, tells Wargamer that the game is not intentionally "extra nor aggravating". This is not a troll meant to target board gamers who scream at the sight of a Monopoly board. Instead, as the Insane Monopoly rulebook says, this is "for those who want even more monopoly when they play Monopoly".
Downin says that Insane Monopoly first emerged in February 2020, "just before everything shut down" in the Covid-19 pandemic. Two developers, Noidea and Lord of Fail played a game of Ultimate Monopoly on Tabletop Simulator.
"Eventually, Noi had the bright idea to 'add' rings onto their own second board and tinkered with the idea with two boards on the same table, with ways to go between each board with some unique mechanics to stand out compared to Ultimate Monopoly", Downin says. One month later, Downin and co-designer Averagejoe were recruited as playtesters for the Insane Monopoly project, which launched on Steam in 2022.
The final result is a Monopoly board that vaguely resembles the classic board game, but it has two distinct boards, nine types of cards to pick up, and numerous rings of spaces to land on. "We added a few extra mechanics on top of Ultimate Monopoly", Downin says, "such as an Investment corner space (which goes up & down periodically through effects) and the Jail Board (instead of waiting for three turns or immediately bailing out of Jail, you go through a small Jail Board with some spaces affecting you)".
Things get even more elaborate with the introduction of the Pyramid Scheme expansion, which covers everything from stimulus checks to schmoozy golf games. "One of my favorite additions being Global Events", Downin says, "which can either instantly take effect or passively affect everyone until it is replaced". "Oh, and the Jail Board in Pyramid Scheme is bigger too."
Downin tells Wargamer that Insane Monopoly is complex, but it's not impenetrable. "Despite what it may look like (a convoluted mess), it's not so bad when you play it yourself for a bit of time".
Time, however, is the biggest challenge of Insane Monopoly. The rulebook says to expect games that last six to eight hours ("for a shorter game, consider a game of chess"). "It definitely is a time sink", Downin says. "With the power of Tabletop Simulator, you can simply save your progress and hop back into it, but doing this physically and in reality, you'd best be prepared for many hours & sufficient rest in between turns."
Despite offering these words of wisdom, Downin still agreed to an in-person game of Insane Monopoly at this year's PAX East. A member of the dev's Discord apparently paid "hundreds of dollars" to bring the board game and its Pyramid Scheme expansion to life. "This session took nine and a half hours", Downin writes on Reddit. "We never managed to get this to completion due to convention hours constraining our time."
Despite this, Downin cherishes the memories made in creating and playing Insane Monopoly. They apparently have no plans to develop it further at this time: "The game is balanced & fun and the lengths that we've already gone into making this a reality just feels right to keep it where it is today."
The original designers may be content with their mammoth creation, but there will always be some mad scientist who wants to dream bigger. Downin says that there's already a spin-off, Insane Monopoly XL, as well as an unfinished Adventure Monopoly RPG project in the works. "It's insane that other people are inspired by our creation to take it upon themselves and create their own experiences", they tell Wargamer.
Have you played Insane Monopoly yourself? We'd love to hear your stories in the Wargamer Discord. Or, for more tabletop games, here are the best board games and new board games to check out.