August 27th, 2016

Winning at Monopoly

Here’s an article that purports to tell you how to win at Monopoly. It has a lot of stuff that anyone who’s played much Monopoly already knows: orange and green properties are good, for example, and nobody lands on Boardwalk much.

How that transfers to strategy I’m not sure. It’s not like anyone shuns owning the orange properties, do they? But you can’t always get what you want, in Monopoly as well as life or Rolling Stones songs.

I used to play a great deal of Monopoly when young. A great, great deal—when we weren’t playing cards or hopscotch or jacks or engaged in jumping rope. That’s what we did—oh, and also that bouncy ball game girls play that went “A my name is…”. In those days, when the internet was hardly a gleam in anyone’s eye and even TV had just a few channels (and in the after-school afternoons they were devoted mostly to soap operas—BORing!), we played games and those were our favorites.

I used to play these games with a neighbor—we’ll call her “Sue”—who was about my age. Actually, she was five months older, as she used to tell me archly and often because it conferred some sort of superiority on her. Sue always won at Monopoly. You may think that to be hyperbole—always? Surely not always!

Yes, always. She had her own never-fail formula. I used to wonder what it was; I still don’t know. Others suggested it involved cheating. But if it did I never detected a particle of it. As far as I could tell it involved unbounded confidence in herself, a confidence that was displayed in every other aspect of her life and which I didn’t share about myself. Can the conviction that you will always win every game you play be responsible for actually winning every game? Even in a game such as Monopoly, that is mostly chance?

Dunno. I merely report: Sue always won. She later became a bigshot lawyer, and I think she usually wins there, too. We’re still friends, but we don’t play Monopoly anymore.

20 Responses to “Winning at Monopoly”

  1. vanderleun Says:

    As a wise man once said to me: “If you want to know what your friends are really, REALLY, like, play Monopoly with them.”

  2. Brian Swisher Says:

    No, van, that would be “Diplomacy”.

  3. M J R Says:

    My mother used to refer to “Monopoly” as “Monotony”,
    and for very good reason (in my rarely humble opinion).

  4. Yancey Ward Says:

    The key to winning is being the banker. Like real life.

  5. Roy Lofquist Says:

    Monopoly is much less a “game of chance” if you play by the rules. Specifically, the starting cash of $1500 per player. You can’t just buy everything you land on. You have to calculate ROI (Return on Investment) taking into account the position of other players on the board. The games also get a lot shorter. Four out of seven anybody?

  6. Trimegistus Says:

    Monopoly was designed to be no fun.

    Seriously: it was devised by a bunch of Single Tax advocates who believed that most social ills were the result of private ownership of property. They wanted all property to be owned in common by the People (i.e. the Party).

    To demonstrate the evils of property, they created “The Landlord’s Game,” all about how capitalism would concentrate all wealth in the hands of the rich, so that everyone else would go bankrupt. (And thus be unable to rent property or buy stuff from the rich, but they never thought that part through.)

    You’re not supposed to have fun playing Monopoly. You’re supposed to be filled with righteous rage against the unjust capitalist system which enables rich guys who own orange lots to oppress the poor who only have purple ones.

    Which makes it totally hilarious that millions of people have had a blast playing Monopoly and the game has made its publishers (but not the commie creators) very rich indeed. I’ll bet the chairman of Hasbro has a mansion AND a hotel on his big orange plot of land in Atlantic City.

  7. Tuvea Says:

    I hardly ever won at Monopoly.
    Or at Clue.
    Or at Risk!
    Or at Mille Bornes ( slam down that Coup-Fourre card! )
    Or at Art Linkletter’s Milton Bradley Game of Life.

    These days I’m so-so at Settlers of Catan.

    But for some reason I almost always won at Careers.

  8. expat Says:

    I was never a game freak, but I did play a few. Mostly I liked sitting on porch swings with a friend and talking about God and the world. My best friend when I was very young lived next door to her grandmother, who a had big honeysuckle bush next to the swing. We loved sucking the honey out of the blossoms. A whole afternoon would probably give you a 16th of a teaspoon of nectar. I also loved playing with the beagle puppies we had. I gave them all names and dressed them up. When Dad gave them away, he had to give me the CV of the new owners.

  9. Mythx Says:

    I have played a heck of a lot of Monopoly. I would say my average was 70% or so among peers. My strategy was very simple.

    First off purchase any property you can. It blocks building and allows for more control of the board through trades.

    Then on every side of the board concentrate on the groups farthest along on each side. Light blue over purple, Yellow over red etc. The reason is each offers a higher return on investment. The houses and hotels cost the same. But you earn more from them.

    The highest return overall are the light blue at the beginning.
    Build them as possible. It allows you to keep chipping away your opponents. While having very little money tied up overall. Next the Orange as they are landed on frequently and still offer a good return. Then build up Boardwalk and Park place. Because once developed they usually bankrupt your competition. Plus having only two properties they are quicker to develop overall.

    If the game is still going I will trade properties to land the rail roads. As they butt up against all your properties and cost nothing to develop. Then the two early purple properties.

    Stay completely away from the Red,Yellow and Green properties. Simply put it takes considerable resources to develop them. And the return on that investment wont keep you ahead of the others. Even when trading properties. I will happily trade those properties one for one for much cheaper ones. And still come out ahead because of the ease of development.

    The utilities I have found to be nearly useless. The only properties I am ambivalent about are the maroon ones just after the jail. You can win with them or without them. They are landed on often but offer middling returns. Overall they are still fairly cheap to develop. I usually use them as sink to hold houses on to prevent development for your opponent. But they are not very necessary.

  10. Mythx Says:


    I am a big fan of the early Axis and Allies. Very fun game but setting up the board could take almost and hour. Time consuming but very fun

  11. OlderandWheezier Says:

    A year or so ago, someone explained their strategy for winning Monopoly…and losing friends. The key was to place about as many houses (3 or 4) as possible on your properties, without ever upgrading to hotels. In doing so, you’ll deprive your opponents of the opportunity to upgrade their own properties, since the total number of houses that comes with the game is limited.

  12. Hangtown Bob Says:

    ” Can the conviction that you will always win every game you play be responsible for actually winning every game?”

    Is this a question applicable to Trump??

  13. huxley Says:

    Can the conviction that you will always win every game you play be responsible for actually winning every game?

    Definitely not true in chess. Even if you are really talented and work really hard, you still lose and often badly while you are climbing the ladder in tournaments.

    It’s a tough game for the ego. Yet it’s hard to keep playing if you don’t have an ego.

    My bet is neo’s friend cheated.

  14. AesopFan Says:

    Mythx Says:
    August 27th, 2016 at 10:26 pm
    I have played a heck of a lot of Monopoly. I would say my average was 70% or so among peers. My strategy was very simple.

    huxley Says:
    August 28th, 2016 at 12:03 pm..
    It’s a tough game for the ego. Yet it’s hard to keep playing if you don’t have an ego.

    My bet is neo’s friend cheated.

    * * *
    My bet is that neo’s friend was able to intuit what Mythx reasoned out for us, and neo doesn’t have the mind-wiring that does the former, and didn’t care enough to do the latter.

    Our block was known for having the oldest floating Monopoly game in town during the summer, but we didn’t have consistent winners and losers, because the goal was to hide out from the grown-ups while still being in the house where it was cool, and talk about Important Things .

  15. Uffdaphil Says:

    fifty+ years ago (~age 12) I found a sure way to win at Monopoly. I traded all my properties to my brother and cousin for the utilities and railroads plus free rent on their real estate. Then I immediately declared myself the winner as I had no outgo, only income.

    Harsh language ensued and free rent side deals were banned in future.

  16. Big Maq Says:

    Mythx is correct. “Stay completely away from the Red,Yellow and Green properties.” – well, only quibble is maybe true if you have a choice – often you don’t. But, agree with the assessment of relative performance ceteris paribus.

    Also played the game many, many, many times. It was both mixed company and serious. 70% winning must be with heavily casual oriented players. Awfully hard to pull that percentage off even with great rolls and superior negotiating skills with opponents who know the ins and outs of the game.

    The game was always most fun when at least one other opponent (preferably all) had a good understanding of the game and had a serious desire to win a friendly game. Too often, if that was not the case, it was either too boring, or was frustrating (e.g. when players would obviously play “favorites”, gave up too easily).

    Not knowing Neo’s age at the time, nor her familiarity with the game (e.g. that three houses was the optimal buildout, that the houses were limited in number, that Free Parking was just that – Free – no pot of money to win, etc), it is conceivable a slightly older child could win every time. It is also conceivable that some form of cheating happened. Impossible to say for sure.

  17. neo-neocon Says:

    Big Maq:

    We played it for quite a few years when we were around 8, 9, 10. We also played Monopoly with our own idiosyncratic rules, at least for a few elements of the game. For example, if we ran out of houses or hotels, we used other items to symbolize them. So, at least theoretically, houses and hotels were unlimited in our games (or limited only by the amount of money we had, which was in turn limited by the amount of money the game provided).

    Another favorite activity of ours was trading doll clothes. I don’t think we ever played with dolls in the conventional manner, but the clothes trading was fierce.

    Perhaps we were strange children. We were great at jacks and hopscotch, though.

  18. Assistant Village Idiot Says:

    My experience was that the strategy was different when it was a two-person game versus multiple players. My multiplayer strategy was similar to the ones noted above, avoiding certain colors and refraining from hotel building. The above are all more detailed and better, however. I guess I wasn’t willing to work hard enough at that.

    In a two person game, mere aggressiveness often wins.

  19. neo-neocon Says:

    Assistant Village Idiot:

    Those were nearly always 2-person games. My opponent was very aggressive, but I tried to be, as well. She tended to have good luck, too—landed on the properties she needed, that sort of thing.

  20. Big Maq Says:

    “Another favorite activity of ours was trading doll clothes. I don’t think we ever played with dolls in the conventional manner, but the clothes trading was fierce. “ – Neo

    Thanks! Had a good laugh reading this.

    Can safely say we never did trade doll clothes, but that is certainly out of the box thinking.

    How fun that would have been for you girls!

About Me

Previously a lifelong Democrat, born in New York and living in New England, surrounded by liberals on all sides, I've found myself slowly but surely leaving the fold and becoming that dread thing: a neocon.

Monthly Archives


Ace (bold)
AmericanDigest (writer’s digest)
AmericanThinker (thought full)
Anchoress (first things first)
AnnAlthouse (more than law)
AtlasShrugs (fearless)
AugeanStables (historian’s task)
Baldilocks (outspoken)
Barcepundit (theBrainInSpain)
Beldar (Texas lawman)
BelmontClub (deep thoughts)
Betsy’sPage (teach)
Bookworm (writingReader)
Breitbart (big)
ChicagoBoyz (boyz will be)
Contentions (CommentaryBlog)
DanielInVenezuela (against tyranny)
DeanEsmay (conservative liberal)
Donklephant (political chimera)
Dr.Helen (rights of man)
Dr.Sanity (thinking shrink)
DreamsToLightening (Asher)
EdDriscoll (market liberal)
Fausta’sBlog (opinionated)
GayPatriot (self-explanatory)
HadEnoughTherapy? (yep)
HotAir (a roomful)
InFromTheCold (once a spook)
InstaPundit (the hub)
JawaReport (the doctor is Rusty)
LegalInsurrection (law prof)
RedState (conservative)
Maggie’sFarm (centrist commune)
MelaniePhillips (formidable)
MerylYourish (centrist)
MichaelTotten (globetrotter)
MichaelYon (War Zones)
Michelle Malkin (clarion pen)
Michelle Obama's Mirror (reflections)
MudvilleGazette (milblog central)
NoPasaran! (behind French facade)
NormanGeras (principled leftist)
OneCosmos (Gagdad Bob’s blog)
PJMedia (comprehensive)
PointOfNoReturn (Jewish refugees)
Powerline (foursight)
ProteinWisdom (wiseguy)
QandO (neolibertarian)
RachelLucas (in Italy)
RogerL.Simon (PJ guy)
SecondDraft (be the judge)
SeekerBlog (inquiring minds)
SisterToldjah (she said)
Sisu (commentary plus cats)
Spengler (Goldman)
TheDoctorIsIn (indeed)
Tigerhawk (eclectic talk)
VictorDavisHanson (prof)
Vodkapundit (drinker-thinker)
Volokh (lawblog)
Zombie (alive)

Regent Badge