Why Games of Monopoly Last Forever

by JT McGee

Everyone says a game of Monopoly lasts forever but they’re wrong; improperly played games of Monopoly last forever.

You know, I manage to put together cheap Wal-Mart furniture without instructions and I never take very seriously the warning labels on OTC or prescription drugs, but I would never, ever play Monopoly without consulting the instructions. Come on people, Monopoly is serious stuff!

Monopoly, board, game, how, to, win

In fact, this is my #1 pet peeve. When someone tells me that they don’t like Monopoly because “it lasts forever,” I immediately either

1) think less of their intellectual capacity

2) assume they have a short attention span.

Next, I ask, “Do you play with a free parking pot?” and almost immediately they say, “Duh.” And then what do I do? I shake my head, then I revisit any conversations I had with this particular person about money, business, or general economic events and throw out anything they may have told me. Creating your own rules for Monopoly on a whim means a severely fractured game layer. Just don’t do it.

When you play Monopoly with a Free Parking pot you bring the 1970’s inflation and price controls to the twenty-first century. The dynamics of Monopoly are structured so that he who is best at evaluating risk to reward wins 99.9% of the time (most games are), but 100% of the time, people who play with the Free Parking pot create such an obscene insurance policy that no one can lose, at least not quickly.

The community chests, tax spaces, and mortgaging/home sales are the only cash drains in the game, and since prices are not set by market dynamics—the price of Boardwalk doesn’t rise with each $200 pass of Go, though it should—you have only mitigated risk at the cost of time. With your goofy rules, everyone has so much cash and so little exposure to risk that we can just waltz around the board without drawing down sufficient amounts to have to exit the game–and that means games that last hours, if not days.

What I find funny is that very rarely does anyone create new Monopoly rules that would disadvantage the average player. How many people do you know play so that property prices are the same, but rents are…uhh, doubled? How many people do you know play Monopoly with $100 payments for passing Go? None? Yeah.

How many play with a Free Parking pot? Tons. I’m sure there’s some behavioral/cultural experiment to be done here, but I’m not Freakonomics–I don’t have that kind of budget! However, I can tell you how not to suck at Monopoly because advice does fit in my budget:

How not to suck at Monopoly:

  • Buy spaces that are structurally advantaged. Any of the orange spaces are excellent, since the jailed crew falls most often on this set. The nearly-broke jailed crew lands on them often, too, since two of the oranges are placed on even numbers, six and eight. Two dice means rolling 6, 8, and 9 is common.
  • Reading Railroad and Boardwalk also fall into the structurally advantaged category. The value of Boardwalk depreciates exponentially after the community chest card prompting a player to proceed to the space is removed from the game. If the card hasn’t been played yet, load up on this space. You’ve an X-1/X chance of mauling someone, where X= the number of players including yourself.
  • The light blues are awesome spaces since they require some of the smallest amount of cash outlay for improvements (save for the not nearly as attractive purple spaces). Smaller minimum investments = more accurate risk management strategies, especially in a game where houses sell on the secondary market for half their purchase price. The rigidity in financing creates inherent dangers that are easily avoided by those who understand the system.
  • Don’t invest all your cash in houses right before you roll your way through a side of the board loaded with opponent owned houses and hotels. Should you leverage up before your roll, you face losing 50% on liquidation and even more paying rent to another player. If I had a dollar for every time I saw someone do this…I’d have so many dollars.
  • There are only so many houses so by owning several inexpensive properties you can effectively restrict every competitor from ever developing their properties. This is the best way to lock down a game. Dollar for dollar, the best return on your investment is achieved with three houses. Rental income rises from $300 to $750 with two to three houses on Illinois, the space most often landed on.

Of course, none of the above matters if you don’t play by the rules. Mr. Hayek has some classic words for people like you:

“The curious task of economics is to demonstrate to men how little they really know about what they imagine they can design.”

{ 21 comments… read them below or add one }

Allison March 7, 2011 at 13:32

Good points. As someone who played Monopoly to excess in younger years (my cousins and I tracked our wins against each other–it was cutthroat), I have no fear of a lengthy game. What I don’t like is how players get kicked out of the game as you go along. Then those players (and they’re never me) have to figure out how to entertain themselves, and it’s usually by starting another game, often a trivia-based board game, and then I’m stuck in the Monopoly game, which quite frankly doesn’t hold a candle to 80s trivia in the Fun Department.

FYI, I’ve found if you’ve got a decent-sized group and they’re playing hard, that Boardwalk card will cycle back through pretty quickly. But still, with as often as that gets landed on, I say you’re better off investing your cash in the yellows (after, of course, conquering the oranges, which are always my first goal.) Interestingly, the yellows are more of a cash cow in a Free Parking pot game, because the pot winner’s next step is often a stay at Marvin Gardens.

Also, I find that Free Parking pot games (and games in which you get $400 if you land exactly on Go–another House Rule I’ve played with) do not insulate players from risk. In my experience, people use the extra infusions of cash to quickly build on properties, leaving them cash poor and having the mortgage up to their eyeballs for a stay on Pennsylvania Avenue.

I’d be interested to know your thoughts on “Short Game” rules, i.e. dealing out the properties instead of buying them as you go.


JT McGee March 7, 2011 at 14:01

Hi Allison,

Thanks for stopping by, and I’m glad to have found someone also interested in Monopoly. It really is a great game!

The structural advantage of Boardwalk should be weighed carefully. As you mention, there are usually better investments to be made, dollar for dollar. However, if the draw pile is getting low and you have the opportunity, it’s a generally decent risk-free way to knock someone out of the game, or severely cripple an overleveraged opponent. Monopoly money is worth more from some opponents than it is from others, and this should not be discounted.

The difference with free parking pot games is that the only exits for cash are home sales and mortgages. While those two actions are usually the largest drain, it just so happens that the home and hotel repair cards (one of the most devastating cards) feeds right into the person who next lands on free parking.

$400 for landing on Go isn’t that big of a deal, but again, there is no flexibility in home and property values, so any new infusions of cash into the game do affect the dynamics. I honestly can’t stand playing with a Free Parking pot because of 1) the inflation that usually follows and 2) how greatly it affects the chance/skill ratio.

Sure, there is plenty of luck that plays into Monopoly, but “luck” in the original rules is usually diluted by large sample size. A free parking pot, though, is given as a massive cash injection for a 1/40 chance of landing on a single space, and it makes other player the beneficiary of the losses of others. Ex. – I pay…say, $500 for hotel and house repairs to the bank for drawing that awful card. That money is gone from the game. Ex with FP, I pay $500 for hotel and house repairs, and that money will eventually land in the hands of another player.

As for short game rules I have so little experience with these outside N64 monopoly I can’t even comment. That particular game had such an awful engine behind it that any experience I had with it wouldn’t even be comparable to a purely human game.


youngandthrifty March 8, 2011 at 02:11

What a unique post! Thanks for planting a smile on my face 🙂 Yeah, I don’t know where the free parking lot idea came about!

Sometimes reading the directions can be so labor intensive though, and board game instructions are so dry at times.

I saw on the news a few weeks back that they have a NEW version of monopoly that is electronic so you can’t cheat. It’s also cashless (so the banker can’t cheat lol). Sign of the times, I tell ya!



Jeff @ Sustainable Life blog March 8, 2011 at 05:32

These are some great tips for monopoly – I happen to enjoy the game very much, but i havent played in ages because no one wants to play with me 🙁
I had never thought about the advantages of the “pot” for free parking and how it changed the game, but I do know the structural advantages of places like boardwalk and my favorite st charles place. The ones with cards directing the players to the property are never a bad deal! My personal favorites are the light purple, orange, red and light blue areas. Some games I go for the railroads, but not always – it seems rather spur of the moment



JT McGee March 8, 2011 at 10:36

@Youngandthrifty – You’re right, sign of the times! You can’t expect those bankers not to cheat, ROFL. That’s hilarious. I like the cashless idea–that’s why I enjoyed playing it on game consoles but that circular board is weird looking. I like the traditional.

@Jeff – I’m the same way with the railroads. I usually go after them if I think I can acquire all four in some form or fashion. To own 1/10th of the board for $800 with cash flow of $200 per landing…mmm, that’s good money. 😀


Denise @ The Single Saver March 8, 2011 at 12:49

Awesome post. As a lifelong fan of Monopoly, I have to agree with everything you said (and am kicking myself for not thinking of some of it myself). If I get around to doing a link round-up this week, you will be in it for sure!


Squirrelers March 8, 2011 at 15:31

Longtime fan of Monopoly. When I was a little kid – and this is well before e-commerce, Barnes and Noble, etc – I actually saved some money and bought a monopoly book at local bookstore (such stores actually existed back in the stone ages). This book gave strategies on how to win at Monopoly.

My motivator was an older cousin who claimed he never lost at Monopoly…and he beat me the few times I played him prior to me buying the book.

After the book? Well, I never lost again! Also remember beating him in a game when he all of a sudden decided to quit since he was losing. It was a bit frustrating since I wanted to take it the distance and get a full victory out of it, but afterward I realized a default win worked ok:)

Last Christmas I bought my 7-year old – correction, SANTA (wink,wink) brought my 7 year old a new edition of Monopoly, ready to pass on the game. Soon discovered she was too young to really get it, and was more interested in quitting and going back to drawing and barbies. Oh well….maybe it will have to wait another year or two. It’s probably good that she’s not just like me anyway 🙂

Have to agree with your tips, by the way – or at least can’t disagree anyway. A few of them


JT McGee March 9, 2011 at 10:51

@Denise – Thanks for stopping by. I’m glad I could bring out the inner boardgamer in everyone 😛

@Squirrelers – Here’s to hoping she learns to appreciate it. Now you’ve got my thinking about getting my <6 month old niece in on that game. 😛


Barb Friedberg March 9, 2011 at 17:07

JT, I am the master of my crowd (my hubby, daughter and close relatives) in monopoly. Of course having a background in real estate, economics and business doesn’t hurt!! This article is so clever, I love it. Even though we pay with the free parking pot, I still manage to win fairly quickly by playing the odds and smart negotiating!!! I LOVE MONOPOLY!! (This one must go in my round up-you are very clever!).


JT McGee March 9, 2011 at 21:40

@Barb – Monopoly is the best. Given how many Yakeziers have responded, maybe it’s time for a Yakezie Monopoly tournament. 😉


SavingMentor March 14, 2011 at 12:39

I love Monopoly too … but I’m getting the feeling that I wouldn’t actually win with this crowd of people, which would be very disappointing because I used to always win back when I played regularly.

We should definitely organize an online Monopoly game … there must be some free place we can all play online right?


JT McGee March 14, 2011 at 15:23

@SavingMentor – Remember, it’s about having fun…not winning. 😛 (Yeah right..) Seriously though, I think there are a few free places to play online…I just hope they have an online version that isn’t to restrictive on trades, deals etc.


Invest It Wisely April 10, 2011 at 22:48

Haha not sure I’d win with this current group of people either. Our games were quite luck-based, but that’s because not only did we seed the free parking with $500 but all of the cards and other payments all went to the middle too. Free parking pots of $2000+ were not unheard of. I wonder why we played that way…. but it was all good fun just the same. 😉

I much prefer monopoly with cash though. It just doesn’t feel the same using the cards and they slow the game down.


JT McGee April 12, 2011 at 02:06

@ Kevin – I think a lot of people do that. It would be fair to say that’s probably my #1 pet peeve. 😛 I haven’t been able to play with the new debit card thing, but I can’t see it being all that great.


John May 12, 2011 at 10:21

Of course, many of these “strategies” are more something to hope for, as opposed to something to strive for. Why? Generally speaking, buying a piece of property requires you to land on that piece of property, before anyone else does. The same conditions that make a certain color group very desirable also make them hard to collect, because theose properties tend to get landed on and distributed rather early in the game.

Unless we are dealing with trades, then, having these strategies won’t help. Unless you’re far more savvy than your opponents, you won’t be able to get exploit these strategies during trades, either.


Maggie@SquarePennies May 18, 2011 at 19:52

JT, I really enjoyed this! Great tips! As a kid we’d play Monopoly games that lasted all day long in the Summer. The part we liked the best was the wheeling and dealing after all the properties were owned. Also there were some real dramas when someone was close to bankruptcy. New partnerships were formed that I’m sure were not allowed by the rules. But it made those games a lot more memorable. And we learned a lot about human nature! lol


JT McGee May 19, 2011 at 12:56

Haha, actually that’s one of the reasons I like Monopoly; there really aren’t that many rules, just a framework that you can build in between. Hah! Lots to be learned about humans, especially greed. 😀


Sean July 18, 2011 at 14:12

Interesting that the pot defeats the designers purpose, which was to teach how Monopolies are harmful to society– you very quickly end up with a single winner and lots of losers. The redistribution of wealth does indeed artificially extend the game.

I’ve often wanted to play a game of Monopoly -with some Tea Party types- that includes the 80% average top marginal tax rate we had for the fifty years prior to Reagan. After about a week of play, they’d say, “My God, this game is NEVER going to end! The rich get richer, the poor get richer — even the WORST player has opportunities to keep from going bankrupt!” To which I’d say, “Yep! SEE ALSO: America: 1933-1980.” 😉


Cameron December 11, 2011 at 17:49

This is a shitty post.

“How to play monopoly: invest in the orange squares and boardwalk.” No, really? Genius.

Free parking collecting fines doesn’t give everyone so much cash that the game lasts forever. Only one person can land on it every 30 minutes for it to have a legitimate impact on THAT ONE PERSON’s cash. And then that person uses his cash to invest in houses, which makes it more likely for him to knock some one else out. Free parking collecting fines is not the thing about Monopoly that gives it the potential to last forever. Not trading is what makes it last forever. For each player, having a monopoly makes his cash level susceptibly low, as houses cost more to buy than they do when you sell them back, and having a monopoly makes this player more likely to knock other players out, as there’s no way 36 dollars in rent will ever do the trick with 200/passing go. Monopolies are necessary for the game to end. Hence the name. With no trading, monopolies are nearly impossible to come by. This is when the game lasts forever. If there’s even one monopoly on the board, the person with the monopoly will win relatively quickly. If there are two, the people that don’t have monopolies will lose very quickly, and the monopoly owner who took out the stronger competitor will have multiple monopolies and will then take out the other competitor, etc. Free parking can just as easily go to the leader in the game as it can to the lowest person, and if the lowest person doesn’t have anything to invest his money on, he’s just running around waiting until free parking fills up again and hoping he lands on it, which is 30 minutes of space avoiding before the free parking space becomes valuable again, and then it’s a ~1/10 chance of landing on it each time it comes close. Odds are this player will be eliminated before free parking pays off anyway.

This article states the obvious about how to play and states the inaccurate about how not to play, using economic allusions that in no way inform correct monopoly gameplay/strategy.

Thanks for sounding smart to a bunch of people without really saying anything informed. You should be a politician.


JT January 31, 2012 at 13:26

Free parking doesn’t have an impact on one person’s cash. It has an impact on everyone’s cash, as it recycles money that would have otherwise left the game. That cash trickles from that ONE PERSON to everyone else. Thus, cash doesn’t leave the game, and the amount of money that exchanges hands from rent becomes relatively worthless due to rampant inflation from the free parking pile.


Jeremy @ Modest Money February 4, 2012 at 02:07

I thought it was a pretty interesting take on a classic game. Sure the boardwalk & orange tip is pretty obvious, but if one is going to list strategies, you can’t exactly leave that out.

I admit I’ve grown up playing the version with free parking money. Some people don’t mind a longer game though. It just extends the fun and adds extra excitement or disappointment when someone does get the big free parking money. Doesn’t everyone want to be able to win the lottery?

By the way, don’t waste your money on that new version with the debit card. The debit card version I tried slowed the game down so much. Since it wasn’t fully automated, you had to manually enter even a $2 rent. Maybe they’ve updated it since then though.


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