Redhook's Revenge

5 February 2023

Board games — you know, like Monopoly, the luck simulator where the only decisions you can make in life depend on what numbers appear on the dice. If it doesn't destroy your relationships, it will at least make you feel like crap when you consider how true-to-life it really is.

And then there's the long list of rules, more open to interpretation than some British legislation. Is building new houses and hotels in jail allowed? Is free parking money a thing? Are unwanted properties always auctioned off?

Frustrating, and yet... it's been ported to so many PC systems, phones, and even the iPod classic. People like this game.

The thing is, Monopoly was devised before computers as we know them today existed. What if you could create a new board game that took advantage of the PC's interactivity and multimedia features? Enter ImagiSoft's Redhook's Revenge.

The Game

In this game, you race against your pirate rivals to reach the other side of the map, which is packed with rich ports to plunder. The aim actually isn't to get there first, though — you win the game if you have the most booty (gold doubloons).

This presents an interesting conundrum: do you take the quickest route in order to raid those ports, or do you attempt to land on every "square" and get as many doubloons from random events as possible? (In which case, having to go back three spaces is actually a good thing.)

Main game screen with a map-like board.

The main game screen.

There are more choices too. As you play the game, you pick up objects that you can either sell, or use to prevent penalties. Profit now, or prevent loss later? You can also choose between two paths at various points.

There's also food, water and rum to consider. If you run out of any of those, you have to pay a non-competitive price for supplies from Redhook himself, and then lose a turn on top.

Another choice involves cannons. You start the game with one, but get the chance to win or buy more as you progress. Always get them when you can, because you need them to win battles.

Pirate Battles

When you land next to a port, or onto another pirate ship, you get the opportunity to fight for doubloons. The amount you get depends on how well you thrash them, but be warned — if you lose badly, it'll cost you instead!

Battle screen showing the dice lined up.

Every cannon involved is represented by one dice. Your roll is sorted by value, highest to lowest, and is then compared to the opponent's roll. Whoever rolled a higher value the most times, wins. (A draw is a win for the aggressor, but with no doubloons changing hands.)


In addition to the music and spoken Blackbeard lines, you learn things about history as you play. Yes, that's right, it's an edutainment game! You get asked questions about piracy, nautical terms, and so on. In return you can win doubloons and other items that might help you win.

Who conquered Sao Salvador, Brazil, in 1624?

Uhhhh... erm...

I don't know how many questions are in the game, I'd estimate about 100, and of course it's easy to cheat in this modern internet-era. But that's the thing — pirates have no rules! Arr.


This game is great for a laugh, and works fine in DOSBox. Luck is still a factor, but there's a lot more entertainment value to the game than Monopoly.

It was released as freeware a long time ago, so download it and have a go!

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