I used to like Monopoly, before its many problems became evident to me. I notice that even in the official excessively mythologizing biography of supposed-creator Charles Darrow, it notes that Parker Brothers didn't believe the game would sell well, and it had to be proven to them from the sales of 5,000 units of the game through department store Wanamakers.

The reasons Monopoly is popular are several, most of them pretty dumb. At this point Monopoly is a part of the culture and lots of people buy it because they don't know there are many much-better games out there. Hasbro merchandises the hell out of it, there's over 4,000 themed versions of Monopoly now. It pushes a pleasing narrative that people can pull themselves up by their bootstraps and become successful (ignoring that all but one of the players will go bankrupt during the game).

What positive attributes does Monopoly have? Well it's ultimately a game about trade, what causes someone to win at Monopoly, in ideal situations, isn't how they move but what trades they make. In nearly every game of Monopoly I've ever played few people ever traded, causing games to run long and winners ultimately decided by whoever managed to make a natural color group, but in principle it's an interesting idea. And it's open-ended, as that mythologizing document I mentioned notes at the time of its origin you couldn't get a game published unless it adhered to certain dogmatic rules, one of which being that it had to have a clear ending. Open-endedness is interesting in a board game, even if, as in Monopoly's case, it can make a game excessively long.

I sometimes muse about how Monopoly could be improved. I think it'd be interesting to make the trading less ad-hoc and random. Maybe only allow trades at certain times, so players would have to think more about when to make them or else lose the chance, and make trades more formalized, maybe with a randomized element? Maybe fewer properties, reduce all color groups to two, make railroads and utilities a bigger part of the game. Maybe an explicit mechanism by which a player can resign from the game. Definitely make bankrupting a player less of a windfall for the person causing it. Definitely increase the costs of owning lots of properties. Definitely set an end point rather than just meander on until all players lose. Maybe add additional reasons to play than just winning; at their best board games tell these little stories about how the game progresses. Maybe have awards for players who circle the board the most times, who spend the least time in Jail, etc. Maybe one or more of these could be a "bar goal," by which I mean, if the players agree ahead of time the players might have to buy the player who wins/gets a specific award a drink or some other minor forfeit.

That's because Monopoly (well, the game Monoopoly ripped off from) was designed to be bad (like Undertale's genocide route). It wanted to show how shitty the stock market is