Defining the Ineffable with Jonathan Kaplan
"It's just fun."
(Merry Christmas, everyone. Hoping your holiday is going well. Hope you’re staying warm and that you’re able to get out on the bike soon.)
launched his newsletter on Substack around three weeks before I did. His newsletter, along with ’s , was the among the first I read.I’m drawn to his writing style, and his “What it Takes” series — where he interviews cyclists and others on what it takes to do what they do — is particularly interesting to me for its journalistic quality.
Jonathan has also worked as a journalist, covering politicians and policy, human rights and democracy in the U.S. and from Iraq, Afghanistan, and Haiti. He’s also interviewed great cyclists, like Lance Armstrong and Tyler Hamilton — among others.
I’ve enjoyed reading his newsletter. Check it out if you haven’t yet. And I appreciated his willingness to participate in “Defining the Ineffable.”
Let's get to know you a bit better.
First, thanks for including me and for your work in local journalism, which is more important than ever. I turned 50 earlier this year and live in Washington, D.C., with my wife, 10-year-old son, and our dog, Stella. In the past, I have worked in journalism and government. Now, I’m a communications officer at the Open Society Foundations, which is one of the largest private philanthropies in the world and works to promote and defend human rights, freedom, and democracy.
What led you to launching Riding with Kaplan?
Let me step back for a moment. I grew up swimming and swam in college, took up running my senior year, and then started cycling after graduate school. I finished the Ironman Hawaii in 2000. Around the same time, I also did some local criteriums and road races (I was really slow!).
When I decided to try to make a living as a writer and reporter in 2001, I wanted to cover either sports and politics. So I started writing about endurance sports. I’ve always been interested in the question “What it takes,” which is the title of a seminal book of presidential politics by Richard Ben Cramer. I love that question. I tried a version of “Riding With Kaplan” a decade ago, but this year we saw a few stages of the TdF in Copenhagen and northern France, and I wanted to give it another go. Substack is a great platform for this project. We don’t have to beg an editor to run our stories and we can promote them as we want. So I mostly write early in the morning or on weekends.
What have you learned about cycling since launching the newsletter?
That is a great question. First, professional cycling is very niche and, without a huge American name or presence at the Tour de France, it is not very popular. Second, the economics of the sport are terrible. The riders deserve so much more compensation and security than finicky corporate sponsors or wealthy investors can provide. Third, it’s really, really hard to make that leap from the U.S. to the WorldTour. You have to be willing to put almost every aspect of your life on hold, move to a place where you don’t speak the language or have a support network, snack only on pickles and popsicles, and race on narrow, steep, old roads against riders from countries where cycling is deeply embedded in the culture. I think Kate Wagner at Derailleur said it best: “It’s all pressure and desperation.”
As a fellow cyclist, I know you have bikes. Can you list off your steeds? (If you can, please provide the year, make and model. And nicknames if you got 'em.)
I currently ride a Specialized Tarmac SL7, 2019 and I have a Cannondale CAAD10, 2013, which I keep on my Wahoo Trainer. I love the Specialized, but my favorite bike of all time was the Klein Quantum road bike I bought in 2000 and used for many years after that.
What is the length of your last ride in hours and miles?
Last Friday, I rode about 20 miles at lunch along Beach Drive through Rock Creek Park (which is a national park) in Washington, D.C. They’ve closed some of it to traffic since the pandemic started and, after much debate, they decided to keep it closed. It is a great network of roads through a major metropolitan area. On Sunday and Tuesday, I rode for an hour or so on Zwift. You can find me on Strava.
Describe the perfect ride for you.
The next step for me is gravel, but for now I’ll stick to the roads. I love riding both with friends and by myself. I really like riding when the temperature gets below 70 degrees in the spring and fall. There are some great rides here in DC. If you can ride 10 miles out of the city, into Montgomery Country, Maryland, the traffic dissipates and there are some good hills by East Coast standards. In an ideal world, I would ride for 90 minutes or so in the late morning.
Describe the feeling that cycling gives you.
FREEDOM. Riding offers the chance to escape the rest of the world. Besides the physical exertion and chance to clear your mind, it’s just fun.
Thanks for reading. Stay tuned for next Sunday’s installment of Defining the Ineffable, when we speak to Trina Ortega, former editor-in-chief of Mountain Flyer Magazine and longtime contributor to the publication based in Colorado. If you like mountain biking, might be worth checking it out. Such great stuff.
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