How A Man Handles His Money Is How A Man Handles His Money

A good friend once said that to me.  How a man handles his money is how a man handles his money.  We were sitting in a cigar shop and we were watching this guy trying to buy a cigar with cash.  His hands went into his pockets and he pulled out a crumpled ball of money that looked like he had retrieved it from the trash.  The customer behind him puffed, and not on a cigar, the cashier (is that what you call them?  why does coffee get a barista but cigars get… cashiers?) sighed and everyone watched the bills fall to the floor, looking like Captain Hook’s origami.   And my friend leans in and says, “How a man handles his money is how a man handles his money.”  Meaning that if your cash is in disarray, good bet your portfolio is, too.

I have a sister (not by blood but does anyone care about that anymore?) who stopped over yesterday.  Her father is in his 90’s, and I knew him well.  He was by no means wealthy, but he bought few and well.  Of everything.  Same car for a decade, but it was sweet car maintained almost weekly.   An honorable man.  A Knight of Malta.  Ran the finances for an Archdiocese into his late 70’s.  Drove that sweet car into the city from Westchester for what, 50 years?

He just celebrated his 75th wedding anniversary in an assisted living facility, and his family is cleaning his house out.  My sister stopped by to give me a hat of his:


I can’t find this hat online anywhere to learn about it, but I bet you it is 40 years old, or older. If you know anything about it, let me know? Thanks!

And yes, the hat is cool and fits perfect.  But what struck me was the old school way it was cared for.  In a box.  Shaped.  Maintained.  Wearable on my head without retouching from day one.  AND a looker.

That is one of the things I am learning to respect as I write this site – people who buy well, buy few, and take care.  It speaks to their character and their values directly (Oh my god he dropped the v word again and he is not perfect!!!).

But what I am also learning is that it creates a legacy, this stewardship of the classics.  It creates an echo as clear as one’s original voice.  With the cancer thing in my family we talked a lot about legacy over the last two months, and then this hat happened yesterday.

This summer my daughter came in and asked to borrow one of my WOCBD’s (oh my god he created an acronym!!!) to wear to the pool over her… well I am going to call it a swim suit but that is a discussion to be held later.  She kept the shirt.  And wears it.  I don’t have a lot of them, this one is an Andover, but it looks good on her and if she wears it when I am gone, that is a good thing to leave behind.

I’m not going anywhere and don’t have cancer – in case that sentence I just wrote made that inference.

It is an Ivy value, and a good target, to build a wardrobe and an asset portfolio and a collection of your belongings that establish who you are in the present, but will also establish who you are as a memory.

And we will all be memories some day.

It would please me to follow in the footstep’s of my sister’s father, and to be able to leave behind a classic, orderly, righteous and good looking legacy.


31 Comments on "How A Man Handles His Money Is How A Man Handles His Money"

  1. Lovely article. Glad I’m not the only one who feels just a little proud when his kids ask to “borrow” his clothes.

  2. I cannot tell you just how resonant this post is for me – by age I’m Millennial, but it constantly frustrates me how rare this attitude has become among so many in my generational cohort, not to mention Gen Z (we can discuss the whys and wherefores another time, and it doesn’t all relate to the aftermath of the 2008 financial crisis). Treating the relationships and things in your life like investments to be cultivated, rather than gimme-gimme disposable flash, will just make you be a better person, and that has nothing to do with age, education, occupation, or political leaning.

  3. Yep! Purchase wisely, and maintain as a habit. Something we are working on with our almost 13-year-old. Not a day goes by that I don’s say to him, “We take care of our things.”

    Kind Regards,


    • Indeed. Another “proud parent” anecdote – we approach things similarly with our 14 year old. This weekend, one of his ice hockey teammates missed a one timer on the powerplay at the end of the period. The player then slammed his stick on the ice twice, trying to break it. My son skated up to him, gave him a fist bump and talked on their way to the bench. After the game I asked my son what he said. He replied “I told him we needed his stick in shape for the next period, and that he’s got to take care of his tools”.

      One of those moments where a parent things, “at least I’ve done something right”.

  4. I agree with Nick. My son has gone away to school this year, leaving a school with no dress code for one that requires him to wear a jacket and tie. At the same time, my father is too old and frail to dress as he once did. And so, the white, blue, and pink OCBDs and repp striped ties that once went daily to practice law are now having a second run in 9th grade. My father is very happy.

    • John Burton | October 17, 2022 at 5:59 pm |

      Ok that is a pretty cool reinvigoration.

    • Jonathan P Scott | November 15, 2022 at 7:11 pm |

      This completely hit me in the feels. What an outstanding connection between grandfather and grandson… and at a time when your son is taking his first steps into the independent world. Huzzah!

  5. John, I appreciate your post today.

    I don’t mean to be Mr. Know-it-All, but I believe a cigar store employee is called a tobacconist.

  6. Future Fogey | October 17, 2022 at 11:46 am |

    WOCBD is an acronym? Should I have been reading it as “wakh-buh-duh” this whole time?

    The hat box is almost cooler than the hat. Almost.

  7. Regarding the first paragraph it is rude to count other people’s money and more so in front of them. The cigar store anecdote is distasteful. You don’t know what that man went through by the time he got to the register. As the saying goes: Be kind, for everyone you meet is fighting a hard battle.

    The rest of the post is good and appreciated.

    • John Burton | October 17, 2022 at 5:56 pm |

      Thank you. We weren’t counting his money, of which he had enough to buy cigars on Madison Avenue. We were noting the disorganization. But you made a good point I need to think about, your idea that we didn’t know what that man went through before he got to the register. That is a REALLY GOOD THOUGHT that did not occur to me. You are 100% right, and I will try harder at that. THANK YOU.

  8. Sage advice all around.

  9. “Captain Hook’s origami” – love this.

    And love the rest of the post as well.

    • John Burton | October 17, 2022 at 5:58 pm |

      I was SO WAITING for someone to notice that. My sister read it and it went over her head. I don’t write much that I like but I thought that part as okay. THANK YOU

  10. “It is an Ivy value, and a good target, to build a wardrobe and an asset portfolio and a collection of your belongings that establish who you are in the present, but will also establish who you are as a memory.”

    The World Wide Web is littered with men’s style websites that worship at the altar of material success. Surely we can do better than to celebrate material wealth above other considerations, such as kindness, love, and empathy. I enjoy this site very much but I also found the cigar story anecdote distasteful as it projects an air of preening superiority. Just my cobbled together “two cents.”

    • I’m not a cigar fan and I see your point Mac. But the cigar-chomping fat cat-types from the old Dana Fradon New Yorker cartoons are probably the primary readership here. The bling-worshipping blogs you refer to are nothing at all like this one. Some I-S readers no doubt have piles of money, others are barely scraping by. A lot of the I-S look is aspirational, but it’s also humble and rather un-materialistic, which is a major theme of this post. No matter one’s tax bracket, there is wisdom here.

  11. Great hat for sure! LOVE the band. I notice a…I don’t know what to call it…a dent in the brim. It’s possible that it’s supposed to be there. Is there another one just like it on the other side? over what would be one’s right ear?

    • Felix Gatto | October 18, 2022 at 1:00 am |

      That “dent” could easily be steamed out.

    • John Burton | October 18, 2022 at 8:27 am |

      Hi – I think that is a shadow? I don’t see it in real life.

    • Marc Chevalier | October 18, 2022 at 12:07 pm |

      It’s usually called a “pinch”, and there are two: one on each side of the front of the hat’s crown. Pinches are commonly placed on fedora-style hats, be they made of fur felt or of straw.

    • Marc Chevalier | October 18, 2022 at 12:12 pm |

      Ah, I misread. Yes, the brim’s left side is bent slightly upward. This often happens to pliable straw hats when they’ve shifted too far to one side in their hat boxes. As @Felix Gatto says, a bit of steaming and reshaping by hand will unbend the brim in less than a minute.

    • That’s what I figured, gents, but then I wonder if it’s more likely to happen when the front is turned down, and the back turned up. I do not wear a hat, but if I did wear a hat, I think I would wear the brim down in front and back, for shade and drainage. Anyway, JB’s hat is a “summer hat”? By the handsome looks of the band, I bet it’s a heyday era BB?

  12. “To leave behind a classic, orderly, righteous and good looking legacy.” Very good. Might I suggest commissioning an heirloom quality family portrait. As for righteousness, there is only one Way, JB. Ivy values are great, but good works, even very good works won’t cut it. And thank you for allowing comments like this➕.

    • John Burton | October 18, 2022 at 8:26 am |

      I don’t know about there being only one way, in fact I am certain there are many. However, if you are encouraging spirituality, that’s a good thing.

  13. Great hat, great story. I’ve also had that sense about folks who keep their cash in loose crumped up wads in their pockets. That said, though I’m quite fastidious with my own billfold, I am utterly terrible with money, so there’s that.
    Continued wishes for your family’s good health and recovery.

    • Speaking of wallets, I am needing a new tri-fold. I’ve looked around. It seems they don’t make them anymore. We’re all expected to live the new digital experience.

  14. “And we will all be memories some day.” In the short-term. The memories will fade.

    You’ll be forgotten. I’ll be forgotten. The vast majority of us will be–yep. Forgotten. How much do you recall hearing about your great, great, great grandfather? How much do you know about your great, great uncle? Here’s a liberating fact: with the passing of decades, most of us will be mostly forgotten.

    Unless you create something that will outlive you and stand the test of time –and by time, I mean centuries. A legacy–with your actual name on (or attached) to it. A published book; an endowment; a building you funded.

    Or you could run for public office of some sort. I don’t know much about my great, great, great grandfather but I can share lots about the governors of my home state who served while he was alive.

    But, again, chances are good the memories of you will last for a generation or two–and then you’ll fade into the foggy, murky mist of history. “Ashes to ashes; dust to dust…” Yep. Most vapor trails disappear…

  15. Angela Uzzo | October 18, 2022 at 2:14 pm |

    As John well knows, I rarely comment on any social media but I felt this article deserved my putting pen to post. My dear not-blood related brother, you captured the essence of Dad so beautifully here and I thank you for this tribute. He will be beyond touched to have his legacy paid such a lovely homage. He certainly is from a bygone era where people took pride and care in the simplest things…when men and women dressed carefully and well…special “suits” donned for traveling and always pocket squares to match ties.

    Among the many things Dad passed onto me was his sense of fashion and the concept of quality over quantity (though this is clearly not reflected in my shoe and handbag collections where I firmly believe the two can happily coexist), to buy well and respect one’s wardrobe. Having adopted these tenets I would like to think that I too am putting together a legacy that I can pass along to the younger women in my life.

    Dad could not have chosen a more fitting recipient for his carefully preserved chapeau and I thank you for championing the “stewardship” of a classic and honoring a life well-lived.

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