Scot Ross wants to send you a letter

Slowing it down with the Wisconsin political analyst.
Scot Ross' gray-green Olympia typewriter is shown sitting on a desk. A sheet of paper with Ross' letterhead sticks halfway out of the top of the typewriter, with illegible typing on it.
Photo by Joel Gratz.

Slowing it down with the Wisconsin political analyst.

This is our newsletter-first column, Microtones. It runs on the site on Fridays, but you can get it in your inbox on Thursdays by signing up for our email newsletter.

Scot Ross wants to write you a letter. I know that because I read all about it on social media, which is a nutty place to read about a guy who wants to write you a letter with a typewriter. On a piece of paper. And then fold it up and put it in an envelope. And then address the envelope. And then put a stamp on the envelope. And then walk it down to the mailbox. You know, about as much time as you spend writing 15 text messages and composing 20 emails. 

Why does Scot Ross want to write you a letter? The veteran political strategist and one-time state-wide candidate for office is restless, looking for new focus. Like for a lot of us, the pandemic seemed to gel a variety of priorities for Ross, not the least of which was losing 300 pounds. He lost 290. An insane accomplishment but the big man had big plans for his mind as well as his body. 

In 2019, he was between jobs, having stepped down as director of liberal advocacy organization One Wisconsin Now and having not yet embarked on his brief but memorable time on the Wisconsin Ethics Commission. “Since I had spent such a long time using words for work, I wanted to keep sharp and thought I could become a ‘person of letters,'” he says. “I dropped some people some letters at the time. Congratulation notes or my misguided thoughts on the current hypocrisies or failings of the day. Sometimes it was, for instance, to encourage someone to run for office, or higher office.” 

The list of reasons goes on, and the bug took hold. Recently he reached out on Facebook and asked people—anyone at all—to private-message him their name and address, and in turn he’d compose a letter to them and mail it. Letter writing, it turns out, is good medicine, and Ross is in excellent company. Saul Bellow was a letter writer. F. Scott Fitzgerald told on himself time after time in his letters. Then there was the fascinating correspondence between two of the greatest American intellectuals of the 20th century: Hannah Arendt and Mary McCarthy. Gonzo journalist Hunter S. Thompson’s letters reveal rage-fueled rants aimed at editors and any other victims the good Doctor happened to scroll into his typewriter. 

And then there’s me. I took special interest in Ross’ new obsession. That’s because, while I don’t use a typewriter, I regularly write postcards to our grown children and to friends. A few of them per week. Writing down your thoughts on paper while knowing the recipient won’t read them for a few more days into the future asks the author to slow down. What do you really want to say? The physical act feels more important than an email. In an odd way, and as everlasting as cyberspace is, it seems more permanent, too. It reminds me of being in the studio as a musician recording on a reel of analogue tape, a finite (and somewhat expensive) medium, as opposed to recording digitally, where one can take 1,000 takes for free. On this difference, Ross and I connect. 

“The immediacy of all our present communications have turned us all into failed mind readers, both anticipating lightning fast follow-up to our keyboard or phone fondling or being concerned or resentful why we aren’t receiving it,” Ross says. When it comes to getting a letter in the mail, he says, “There’s nothing better than an unexpected gesture and at an unexpected time.” 

Ross composes his letters on a very special typewriter. The 1959 Olympia model belonged to his mother who received it from her parents as a youngster on the rural Pennsylvania farm where they lived. I’ll let Ross finish the story. It’s kind of a long one. Longer than my Tone Madison editors would generally stand for inside one paragraph of quotes, but hey. This is a story about slowing down with words. 

“She took that typewriter to a teachers’ college, north of where she grew up, and also where she met my old man. The typewriter still had its indestructible pea green 1970s Dodge Dart Swinger-colored carrying case. I was home in the spring of 2014 and found it while I was in our attic. I asked my Mom if I could take it and get it fixed up to use. She said yes, of course, and I drove it back across this once-great republic to Jeff at J&G Office products in Janesville. That the only typewriter repair place I found anywhere near me is literally on the route as one would drive from my boyhood digs to my current place in Madison has to be some kind of power greater than myself at work. Jeff did an amazing job. We had to find some parts to replace. J&G helped me locate a similar machine online, which I purchased and gave to them to [use to] fix. They even were kind enough to keep the machine amongst their office filled with typewriters. In case other things go on mine, they will have more brains to feed my zombie machine, which they brought back from the dead.”

The machine has spiritual power for Ross. Here’s another long quote about that, one that will also try the patience of my digitally minded editor. 

“My Mom got diagnosed with all the shitty cancers in 2014 and left this mortal coil in spring 2015, so I display her repaired typewriter prominently, as a reminder that she was, sorry everyone else, the best Mom ever. My Mom was a middle-school English and reading teacher for more than 30 years and I remember the sound of the bell of her typewriter from when I was a kid as she would be typing papers at the kitchen table to be reproduced and passed out to her students.”

Since telling the world that he’s open for letter-writing business, Ross has received about a dozen requests. Topics requested include Ross’ view of gardening, how hard it is to quit smoking, and the atrociousness of bringing giant tubs of salad dressing on airplanes. Overall, what does he think makes a good letter?

“You need a strong opening. Either something short and punchy, or open lines which dart to an unexpected location,” he says. “The thing about using a manual machine is that you have to type your way out of words that come to mind and suddenly seem ill-conceived. You can’t just backspace and asterisk over them. That feels like cheating. You laid the path for the reader to follow and it’s your responsibility to guide them to the exit.” 

I plan to let Ross know when this story goes online by sending him a postcard.

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