Reflections on Route 66: A Journey Through Time

Few Americans have been as explicit in their warnings about Donald Trump than the St. Louis based writer Sarah Kendzior. Her latest book, The Last American Road Trip, is a memoir chronicling Kendzior’s journey down Route 66 to show her children America before it is destroyed. Borrowing from her research of post Soviet Central Asia, Kendzior argues that Trump is establishing a kleptocratic “mafia state” designed to fleece the country of its valuables. This is the third time that Kendzior has been on the show and I have to admit I’ve always been slightly skeptical of her apocalyptic take on Trump. But given the damage that the new administration is inflicting on America, I have to admit that many of Kendzior’s warnings now appear to be uncannily prescient. As she warns, it’s Springtime in America. And things are about to get much much hotter.

FIVE TAKEAWAYS

* Kendzior views Trump's administration as a "mafia state" or kleptocracy focused on stripping America for parts rather than traditional fascism, comparing it to post-Soviet oligarchic systems she studied as an academic.

* She believes American institutions have failed to prevent authoritarianism, criticizing both the Biden administration and other institutional leaders for not taking sufficient preventative action during Trump's first term.

* Despite her bleak analysis, Kendzior finds hope in ordinary Americans and their capacity for mutual care and resistance, even as she sees formal leadership failing.

* Kendzior's new book The Last American Road Trip follows her journey to show her children America before potential collapse, using Route 66 as a lens to examine American decay and resilience.

* As an independent voice, she describes being targeted through both publishing obstacles and personal threats, yet remains committed to staying in her community and documenting what's happening.

FULL TRANSCRIPT

Andrew Keen: Hello everybody, it is April the 18th, 2025, a Friday. I'm thrilled today that we have one of my favorite guests back on the show. I call her the Cassandra of St. Louis, Sarah Kendzior. Many of you know her from her first book, which was a huge success. All her books have done very well. The View from Flyover Country. She was warning us about Trump and Trumpism and MAGA. She was first on our show in 2020. Talking about media in the age of Trump. She had another book out then, Hiding in Plain Sight, The Invention of Donald Trump and the Erosion of America. Then in 2022, she came back on the show to talk about how a culture of conspiracy is keeping America simultaneously complacent and paranoid that the book was called or is called, They Knew. Another big success. And now Sarah has a new book out. It's called The Last American Road Trip. It's a beautifully written book, a kind of memoir, but a political one, of course, which one would expect from Sarah Kendzior. And I'm thrilled, as I said, that the Cassandra of St. Louis is joining us from St. Louis. Sarah, congratulations on the new book.

Sarah Kendzior: Oh, thank you. And thank you for having me back on.

Andrew Keen: Well, it's an honor. So these four books, how does the last American road trip in terms of the narrative of your previous three hits, how does it fit in? Why did you write it?

Sarah Kendzior: Well, this book kind of pivots off the epilog of hiding in plain sight. And that was a book about political corruption in the United States and the rise of Trump. But in the epilogue, I describe how I was trying as a mom to show my kids America in the case that it ended due to both political turmoil and corruption and also climate change. I wanted them to see things themselves. So I was driving them around the country to national parks, historic sites, et cetera. And so many people responded so passionately to that little section, especially parents really struggling on how to raise children in this America that I ended up writing a book that covers 2016 to 2024 and my attempts to show my children everything I could in the time that we had. And as this happens, my children went from relatively young kids to teenagers, my daughter's almost an adult. And so it kind of captures America during this time period. It's also just a travelog, a road trip book, a memoir. It's a lot of things at once.

Andrew Keen: Yeah, got great review from Ms. magazine comparing you with the great road writers, Kerouac, of course, and Steinbeck, but Kerouak and Steinback, certainly Kerouack was very much of a solitary male. Is there a female quality to this book? As you say, it's a book as much about your kids and the promise of America as it is about yourself.

Sarah Kendzior: Yeah, I think there is in that, you know, I have a section actually about the doomed female road trip where it's, you know, Thelma and Louise or Janet Bates and Psycho or even songs about, you know, being on the road and on the run that are written by women, you know, like Merle Haggard's I'm a Lonesome Fugitive, had to be sung by men to convey that quality. And there aren't a lot of, you know, mom on the Road with her husband and kids kind of books. That said, I think of it as a family book, a parenting book. I certainly think men would like it just as much as women would, and people without kids would like just as people with kids, although it does seem to strike a special resonance with families struggling with a lot of the same issues that I do.

Andrew Keen: It's all about the allure of historic Route 66. I've been on that. Anyone who's driven across the country has you. You explain that it's a compilation of four long trips across Route 66 in 1998, 2007, 2017, and 2023. That's almost 40 years, Sarah. Sorry, 30. Getting away my age there, Andrew. My math isn't very good. I mean, how has Route 66 and of course, America changed in that period? I know that's a rather leading question.

Sarah Kendzior: No, I mean, I devote quite a lot of the book to Route 66 in part because I live on it, you know, goes right through St. Louis. So, I see it just every day. I'll be casually grocery shopping and then be informed I'm on historic Route 66 all of a sudden. But you know it's a road that is, you once was the great kind of romanticized road of escape and travel. It was decommissioned notably by Ronald Reagan after the creation of the interstate. And now it's just a series of rural roads, frontage roads, roads that end abruptly, roads that have gone into ruin, roads that are in some really beautiful places in terms of the landscape. So it really is this conglomeration of all of America, you know of the decay and the destruction and the abandonment in particular, but also people's, their own memories, their own artistic works, you know roadside shrines and creations that are often, you know pretty off beat. That they've put to show this is what I think of our country. These are my values. This is what, I think, is important. So it's a very interesting journey to take. It's often one I'm kind of inadvertently on just because of where I live and the direction I go. We'll mirror it. So I kept passing these sites again and again. I didn't set out to write this book. Obviously, when I first drove it when I was 19, I didn't know that this was our future. But looking back, especially at technological change, at how we travel, at how trust each other, at all of these things that have happened to this country since this time, it's really something. And that road will bring back all of those memories...