For as long as I can remember, I had a strong distaste towards the game Monopoly, which few of my friend group seem to understand even after my frequent attempts at explanation. My reasoning is because the game is almost entirely luck based, with dice driving every bit of it. This causes the game to be based on luck with little to no strategy. Don’t get me wrong, I recognize that board games require randomness to have long term playability, but when a game goes off the deep end and becomes only random as to who wins, then the game shouldn’t be played.
Monopoly is a game whose roots go back to a 1903 anti-monopolist named Elizabeth Magie Phillips, who created The Landlord's Game as an attempt to explain single tax theory and why it was bad. The Landlord's Game had many variations made of it, and in 1935 a variation of it was made. It was called Monopoly, which is the version the Parker brothers picked up to turn into the game we all know today.
Monopoly is regarded by some as a classic game, but at least in my opinion it is an awful game that shouldn’t be played, as there are numerous better board and card games in existence that would be much more fun. The game is designed in such a way that only one person is going to have fun, and that would be the winner.
The game is almost all luck of the draw. Movement is done via dice rolls, or through a card draw. If you buy an (unowned) property is not typically a strategic decision, it is instead do you have the money to buy it? If you do, buy it, if not you auction it, with auctions being one of the two strategic decisions allotted to the player. The other being that if a character has a get out of jail free card, do they use it or try to hide in jail. Other than that all the mechanics benefit whoever is already in control, or to shake up the board in the early game. Past the early game, the cards do little to shake up the game, except for the few ones that charge you per house/hotel.
Once the early game is sorted out, barring a bit of bad luck, whoever is the current winner is very likely to win overall. Whoever ended up the best in the early game will have more properties, meaning others are more likely to land on their owned properties. As players drop off cash-wise, they end up having to mortgage properties, meaning it becomes difficult to get back in the game, as there are now less properties to earn money off of. This cascading slope game play drives the final nail in the coffin for me, as you are either having fun and winning, or bored out of your mind.