Episode 280: Upset the Apple Cart

This week Shauna and Dan try not to upset the apple cart. Bonus: The USA's earliest pen pals, wizardly cats, and Gudrun Lauret's disruptive creators (or possibly creative disruptors)

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Bunny Trails: A Word History Podcast
Episode 280: Upset the Apple Cart
Record Date: June 1, 2025
Air Date: June 11, 2025

Intro

Shauna:
Welcome to Bunny Trails, a whimsical adventure of idioms and other turns of phrase. 

I’m Shauna Harrison

Dan:
And I’m Dan Pugh

Each week we take an idiom or other turn of phrase and try to tell the story from its entry into the English language, to how it’s used today.

Opening Hook
Have you ever been in the middle of something and things were going so well, only to have something come in at the last minute with an unexpected problem causing everything to fall apart? And then you are scrambling around trying to put all the pieces back together again. Well that is the concept of “upset the apple cart”.

Meaning
According to the Oxford English Dictionary, to upset the apple cart means:

Quote
to cause an upset or disturbance
End Quote
https://www.oed.com/dictionary/apple-cart_n?tab=meaning_and_use#346380 

An interesting note about this is the Oxford English Dictionary made a note that there is minimal evidence for the literal usage of the term “apple cart” before 1767, so it is likely the phrase would have sprung up around the literal usage of a cart that hauls apples. This likely dates the phrase to the mid 1700s, which does match what we have found so far. 

1788
And while we currently use the phrase to mean causing an upset or disturbance, it’s important to note the phrase originally meant to harm a person or knock them over, as we see in this definition from Francis Grose’s 1788 work, A Classical Dictionary of the Vulgar Tongue:

Quote
Apple Cart. Down with his apple-cart; knock or throw him down
End Quote
https://www.google.com/books/edition/A_Classical_Dictionary_of_the_Vulgar_Ton/4HoSAAAAIAAJ?hl=en&gbpv=1&dq=%22apple+cart%22&pg=PP33&printsec=frontcover 

1750
I could only find one example of this usage in print, and it’s from a work called Another Fragment. This is dated circa 1750. It was a story the unnamed editor of the work said was relayed to him by a Professor at the University of Cambridge.

Quote
Now Dun was universally hated among the Boys, because he us’d to carry a great Stick in his Hand to frighten them Home from their Play, making them come in by Daylight to go to Bed, or read good Books, for which Reason whenever his Back was turn’d, they would make Faces at him, and us’d to beryme him, calling out hoo! Doctor Proctor! - hoo! Doctor Proctor, and so on; for which, however, whenever he catched’d them, he down’d with their Apple Carts, and made them smart for it.
End Quote
https://archive.org/details/bim_eighteenth-century_another-fragment_1750/page/n7/mode/2up?q=apple 

That’s the only example I could find of this usage, but as we’ve discussed on the show before, the kind of works that survive long enough to be digitized are usually written in a style befitting what was considered by those with power as an appropriate manner. Francis Grose captured terms and phrases that were considered inappropriate. As such, we don’t have much historical documentation of this phrase prior to its inclusion in Grose’s work. 

1788
We do, however, have contemporary works of Grose’s using the phrase in the way we would use it today. Here is an example from a letter written February 10, 1788. The letter was written by Jeremy Belknap to Ebenezer Hazard, two prominent men during the American Revolution. They wrote on all manner of subjects, but this one was referencing the ratification of the United States constitution. These letters have been heralded as an intimate look at day-to-day life during the time. The quote I will read mentions an S. Adams who you may know as Samuel Adams.

Quote
How long this Federal frolicking will hold, I know not. S. Adams had almost overset the apple-cart by intruding an amendment of his own fabrication on the morning of the day of ratification. 
End Quote
https://archive.org/details/collectionsofmas00mass_33/mode/2up?q=%22apple+cart%22

This was a fascinating subject. I really enjoyed seeing Belknap’s take on Samuel Adams amendment, which was quickly removed. But it caused quite a stir. So we’ll look at the entire letter, which is part of the Collections of the Massachusetts Historical Society in our behind the scenes video, which airs every Friday on our patreon, Patreon.com/bunnytrailspod  

1837
Here’s an example found in the The Champion and Weekly Herald out of London, England, dated April 17, 1837. It is from a speech delivered to a group in opposition to the poor-law amendment bill. 

Quote
The Whigs, Gentlemen, cannot object to the soundness of our old authorities in law, because, you know, they themselves are very fond of referring to the same source, when it suits their purposes; and to deny those authorities, therefore, would be at once to upset their own apple cart.
End Quote
https://newspaperarchive.com/london-champion-and-weekly-herald-apr-17-1837-p-7/ 

1841
This next is a humorous and I hope overblown story out of the Chronicle and Gazette and Kingston Commercial Advertiser out of Ontario, Canada. This is dated May 26, 1841. It is titled, “Making Sure”.

Quote
A few days ago, in Rochester, NY, an apple merchant, by the name of Richard McMaster, was charged with “upsetting the apple cart” of one Daniel Simeone, who was also a dealer in apples. The Judge, after hearing the case, was exceedingly puzzled to ascertain which was most in fault; but to make sure that the guilty one should not go unwhipped of justice, he sent them both to prison. 
End Quote
https://newspaperarchive.com/kingston-chronicle-and-gazette-may-26-1841-p-1/ 

1893
This next one is from the 1893 work From Whose Bourne and other stories by Robert Barr. 

Quote
Well, sir, I must admit, that although I have known George Stratton for years, I thought he was dished by that Cincinnati lawyer. I thought that George was just gracefully covering up his defeat, and there he upset old Brown’s apple-cart in the twinkling of an eye. 
End Quote
https://archive.org/details/fromwhosebourneo0000barr/page/56/mode/2up?q=%22apple+cart%22 

1916
This next one had me rooting for the wife in a story called “Confessions of a Wife”, a serialized story, with the wife as the narrator, I found published in The Day Book out of Illinois, USA, dated January 7, 1916.

Quote
“Yet, my dear, I am very much like other men. We welcome anything, everything, to vary the monotony of business. No matter how much we try to be straight and decent members of society we all want to 
and most of us do 
‘kick the apple cart’ occasionally.” 

“But what of us women, Dick?” I broke in. “Are our lives so much more diverse than your that we must be content with what little part of yourselves you men must give us? What is there so wonderful about ‘kicking over the apple cart’ that you cannot resist it? No, don’t try to speak, Dick. You would not tell me the truth, but I warn you that if in the future I too feel like ‘kicking’ I shall do so. No question of conventionality or even morality shall keep me from it.”
End Quote
https://chroniclingamerica.loc.gov/lccn/sn83045487/1916-01-07/ed-2/seq-25/ 

1928
George Bernard Shaw’s 1928 play, The Apple Cart, is a satirical work that highlights political intrigue as multiple forces attempt to upset the apple cart either through destroying the status quo, or vigorously defending it. Britannica had this to say about the play:

Quote
…he produced The Apple Cart (performed 1929), a futuristic high comedy that emphasizes Shaw’s inner conflicts between his lifetime of radical politics and his essentially conservative mistrust of the common man’s ability to govern himself.
End Quote
https://www.britannica.com/biography/George-Bernard-Shaw/International-importance#ref78575 

There have been numerous updates to this play and a quick look at the search engine of your choice should net you a variety of updates you can read if you so desire. And while I didn’t include any modern versions of the play in our modern uses, you can be assured the play still gets love even today. 

1946
Here is one from the Bruce Rock-Corrigin Post out of Western Australia dated June 27, 1946. This is from an article called Warning to Wasters of Money and calls out bad actors who upset the market for their own gain at the expense of the common good.

Quote
The weak link in this credit chain is the man with money to spend while goods are short. He can upset the apple-cart with a vengeance by lending his spending power to the forces which would overturn a system set up for the general good. Once the apple-cart is upset, that is to say, once inflation begins, it grows by its own momentum.
End Quote
https://newspaperarchive.com/bruce-rock-post-and-corrigin-and-narembeen-guardian-jun-27-1946-p-1/ 


So as far as we can tell, Upset the Apple Cart as a figurative entered the language in the mid 1700s, which may have coincided with literal apple carts joining the language. And while the earliest uses meant to knock someone down or otherwise hurt them, it quickly took on a less sinister tone and has now long been used to identify some sort of disruption to the status quo. 

With that, it’s time to move to our more modern uses but first we need to say thank you to our sponsors. 

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Modern Uses

1952
Let’s kick off our modern uses with You Upset My Apple Cart, a 1952 single released by Jimmie Allen. It’s a bluegrass inspired Country and Western song. The song opens with the lyrics:

Quote
When you upset my apple cart
I thought at first it broke my heart
Because I had my heart set on you
But I’ve already got a plan
To fix my wagon up again
I look around and find me someone true
End Quote
https://archive.org/details/78_you-upset-my-apple-cart_jimmie-allen-scrivner_gbia0461383b 
https://www.youtube.com/watch?v=-YgbxK8lyfU 

1972
This is from the periodical Army Logistician. This is from a speech given on 18 May 1972 by General William C. Westmoreland about Materiel Management. Here is a snippet from the article:

Quote
If your organization, section, division, or branch is not to stagnate, you must reward your innovators. Most importantly, and this is most difficult, you must give them a chance to make mistakes. Innovators will not blossom without a great deal of coaxing, and often - and I know you are aware of this - what innovators suggest will tend to upset the apple cart … When the apple cart gets in the way of our higher objectives, so much the worse for the apple cart. 
End Quote
https://www.google.com/books/edition/Army_Logistician/Zis2rWH-LHMC?hl=en&gbpv=1&dq=apple+cart&pg=RA9-PA15&printsec=frontcover 

2018
Here’s a clever title playing on the phrase about the company Apple. It comes from the Denver Post’s online website published April 20, 2018. It was written by Mario Nicolais, an attorney and Denver Post columnist who writes on law enforcement, the legal system and public policy. Here is the headline:

Quote
Apple attempts to upend the electronic health records cart
End Quote
https://www.denverpost.com/2018/04/20/apple-attempts-to-upend-the-electronic-health-records-cart/ 

The title is interesting because it plays with the company name, Apple, and recognizes the phrase apple cart, but makes the cart about electronic health records. This is one of those headlines that makes perfect sense if you are a native English speaker, but could really cause confusion for someone learning English. 

2021
Melissa King: Applecart by Robert Finkelsen is a 2021 fiction novel. It is the second book in the Melissa King series. Here’s the synopsis from the publisher:

Quote
Several years ago Melissa left her small town in Massachusetts after obtaining her degree in journalism to join the Los Angeles TV networks “first on the scene news team.” As a reporter she discovered the dangerous world of investigative reporting. While investigating a series of mysterious deaths from all over the country, she stumbled upon a secret government project called Applecart. As she weaved her way through the investigation, against the advice of her supervisor; she placed herself and her closest friends’ lives in danger. The consequences of ignoring that advice will plague her forever.
End Quote
https://www.google.com/books/edition/Melissa_King_Applecart/3josEAAAQBAJ?hl=en&gbpv=0 

2023
Don’t Upset the Apple Cart is a song by Joel Dobbins off the 2023 album You Know Who You Are. It’s a song about copying the lifestyles of the rich and famous, despite not being rich and famous. I have no idea what this style is. It’s definitely satirical, but it’s almost performed as a novelty song. Reminds me of many songs I heard growing up listening to Dr. Demento on the radio. Here is the chorus:

Quote
Don′t upset the applecart
Don't keep me and my next apple apart
Don′t upset the applecart
My personal debt has given me a headstart
End Quote
https://www.youtube.com/watch?v=eI1SOh6y98Q 

2025
The Apple Cart is a podcast that began in January 2025 and is hosted by Gudrun Lauret. Here is the overview from Apple Podcasts: 

Quote
An interview show, with a new guest each week. We explore creativity, marketing, business and work-life balance, as well as a whole host of other topics. This is for you if you're a disruptive creator, a creative disruptor or you want to do things differently in business and leave the world a better place. The shows are sometimes NSFW, sometimes funny, but always fun, valuable and with insightful nuggets.
End Quote
https://podcasts.apple.com/gb/podcast/the-apple-cart/id1791574744 

She noted in her episode zero the name is specifically an allusion to business owners who challenge the norms with their work. 

Wrap Up
And I appreciate “upset the apple cart" because it does capture the idea of challenging the status quo. It’s a sense of shaking things up when everything feels too settled or predictable. I think there is something empowering in the notion of disrupting the norm. But beyond its meaning, I also love the vivid image it conjures which I see in a cartoonish style - a cart brimming with apples tipping over, spilling fruit in all directions. It’s a whimsical mental picture, one that blends chaos with something new and exciting emerging from the disruption. Visually, it represents both the risk and reward of change.

Dan:
That’s about all we have for today. If you have any thoughts on the show, or pop culture references we should have included, 
reach out to us on Patreon, patreon.com/bunnytrailspod or comment on our website bunnytrailspod.com

Shauna:
It’s poll time!

Recently we asked our patrons, if you could pick any style of music to wake up to in the morning, what would it be?

A full half of our Patrons said they’d want something low and slow for a soft, steady pace to help me wake up peacefully. In second place was something jazzy, with some highs and lows and a wandering melody. Third was something upbeat but not to heavy - like a Sunday brunch kind of music. And in a distant fourth, almost honorable mention territory, was something fast paced and rocking to get me started

JGP shared:
Quote
I tend to get woken up by my cat before my alarm can start playing anything. Supposedly maine coon cats have 'enchantingly melodic trills' but… if I'm late for his breakfast my cat wakes me up with something a little less pleasant sounding.
End Quote

Dan:
Heather said:

Quote
Instead of music I usually wake up and put a podcast on. Something about someone talking about topics I enjoy gets me up & through my routine.
End Quote

I feel that. I used to wake up to the BBC news every morning. These days I don’t want to hear about the news of the world. My favorite thing to wake up to is the sounds of nature as the sun begins to peek into the windows, but I live in the suburbs so light pollution means my blinds stay shut overnight and I’m more likely to hear lawnmowers than birdsong. So instead I like waking up to some old school jazz, like Duke Ellington or Dizzy Gillespie. 

Shauna:
Mary said:
Quote
I have my Alexa set to either Diana Krall or Native American Flute music. Both are great for the peaceful emergence from warm coziness. I can also go right into my yoga or stretching routine without an abrupt change or crashing my brain. 
End Quote

I love this for Mary. Unlike most of this group… all of this peaceful, soothing, calm music is likely to send me back for another full round of sleep. My brain would think… you have nothing to do right now… enjoy your magical dreams. My alarm, however, is really obnoxious - a cross between the jeopardy theme and muzak. Because I need it to be mentally intrusive enough to make me take action. Then once I’ve gotten out of bed, I usually opt for something with a good beat. The genre can change daily but classic rock is a safe bet. 

As a reminder, our silly polls mean absolutely nothing and are not scientifically valid. And patrons of all levels, including our free tiers, can take part. Head over to patreon.com/bunnytrailspod to take this week’s poll!

Outro 

Shauna:
Thanks for joining us. We’ll talk to you again next week. Until then remember, 

Together:
Words belong to their users.