Thursday, May 26, 2011


Elaine’s, one of my favorite places in New York, is closing tonight. Elaine Kaufman, the longtime owner—and one of the best friends a writer could have—died a few months ago, and the joint just couldn’t manage without her.

One of the best nights of my life was spent at Elaine’s, in the company of writers old and young, at the wake held for W.C. Heinz, who wrote “Death of a Racehorse”—from which this blog’s name was lifted—among many other great things.

A few of us read “Death of a Racehorse” out loud to an audience that, had I been less drunk, would have made me shit my pants just by its having assembled. Later, five of us ended up at a round table together: Charles P. Pierce of Esquire and the Boston Globe; ESPN’s Wright Thompson and Jeff MacGregor; and Kevin Van Valkenburg of the Baltimore Sun.

It was one of those great, beautiful nights when we shared each other’s dreams and stories and company. I could never do justice to it.

Luckily, Kevin Van Valkenburg can. He’s done us the favor of writing about it, and allowing me to post his words here. My thanks to him for that.

Kevin’s a great man—a husband, a father, a writer, a traveler, a drinker, a reader, a romantic, and a beast. But mostly Kevin’s a dreamer. Of the five of us, I would bet that he’s the one most likely to have already been on the moon.

If this is your introduction to him, I hope you like what you read here. You’ve been missing out. If you know Kevin, well, then you already know what you’re in for: You’re in for grand company, which is what Elaine’s was all about, on our night there, on every night there, and now, tonight, with closing time coming down hard, and just enough time for one last wake.

Mr. Kevin Van Valkenburg, the floor, my friend, is yours:

Monday, May 16, 2011


I don’t know Drew Magary. I know his writing, mostly through Deadspin and Kissing Suzy Kolber. I can’t remember how I came to read an advance copy of his first novel, The Postmortal—I feel like he whored himself out to me, but I might have pestered him, because he’s one of those guys I’ve always wondered about, and not just in a metaphysical sense. Either way, it doesn't matter: The Postmortal is good. Really good. I’ve already attached myself to write the screenplay (I’m not sure if Drew knows this yet) for what will surely be a popular and critically acclaimed blockbuster about immortality, the meaning of life, and women with impossible bodies.

You can pre-order your very own copy here.

What’s weird for me about this particular Five for Writing—apart from its comparison of personal watercraft to breasts—is that I actually found it kind of unsettling. I’ll write more about this later, but I felt like Drew was speaking to me when he wrote what he wrote about guys who write on typewriters. I like to think writing is IMPORTANT, because it’s what I do. But maybe, when you strip it right down to its most basic elements, it’s just putting words in an entertaining order in exchange for money. Reading this made me wonder whether I’ve been squeezing the bat a little too hard lately.

Anyway, maybe a little more than usual, I’d like to thank Drew Magary for joining the Five for Writing circus. Despite the fact that he puts two spaces after every period—fixed—I really like what he wrote here, and what he wrote between the covers of his new book. I hope you do, too:

Thursday, April 14, 2011


I’d like to tell you a story about Gregg Doyel.

Gregg and I began corresponding a few months ago, after he got into it on Twitter with my Esquire colleague Scott Raab. Their skirmish made me sad, because for reasons I can’t really explain—their passion, their abiding sense of morality—I had decided that they would actually get along famously in real life.

So, I asked them to make up. More specifically, I asked Gregg to make up with Scott. Now, Gregg once got challenged to a fight by an angry MMA dude and accepted. He’s not exactly known for backing down. But Gregg and Scott eventually patched things up, and one night we’ll meet for dinner in Cleveland or Cincinnati or somewhere in between (Xenia?) and have a grand time. That makes me happy.

Anyway, Gregg and I have maintained our correspondence, and one thing Gregg does a lot is make fun of his own abilities. He’s always saying that he’s not capable of this, or he wouldn’t be able to contribute to that. When I asked him to do a Five for Writing, he said that he’d read the past entries, and he didn’t belong in the same company.

Well, let me tell you another story about Gregg. He received these five questions at 9:52 a.m. this morning. Three minutes before noon, I had 2,400 clean, precise, entertaining words land in my inbox. You can’t do that if you’re not made for this game. You can’t write like that, have the words just pour out of you, if you’re not built to do this.

I’m very pleased to introduce Gregg Doyel, esteemed member of Five for Writing’s Class of 2011. He belongs.

Monday, April 4, 2011


Glenn Stout is a man of many projects. Among fans of longform sports writing, he’s perhaps best known as the editor of the vaunted Best American Sports Writing series. (The 2011 edition, guest edited by Jane Leavy, will be released in October.) He’s also written dozens of his own books, covering a wide variety of topics, from baseball to the World Trade Center site to Trudy Ederle, the first woman to swim across the English Channel.

Glenn’s next book, Fenway 1912, is about the building of that ballpark and its first season. It will also be released in October.

I admire Glenn for his having forged a career mostly as an editor and author of books—a very tough nut to crack—but also because of his continued interest in helping develop young writers and readers. Glenn treats the words that make it into print like an inheritance, like objects that are being passed down. And I believe he wants, more than anything, for those words to be good—to be worthy—and for them to continue to be good. I don’t know anyone who’s done more to seek out and highlight bright new talent. He’s like an old birddog scout, and I can still remember the first time he found me. Getting a phone call from Glenn, telling me I’d made BASW, was one of those moments I’ll remember happily forever.

Many thanks to Glenn for taking the time to participate in Five for Writing. There are many lessons here worth noting if you, too, wish one day to be collected.

Sons and Daughters of Bold Venture—Vermont’s own, Glenn Stout:

Monday, March 7, 2011


Charlie Pierce is one of the reasons I became a writer, or at least one of the reasons I became the writer I did. When I was in school, I read Esquire with religious fervor, which meant, mostly, that I read Charlie’s sports column, “The Game,” and anything else he’d written over the course of his long and varied career. I became obsessed with many things about him: his limitless-seeming knowledge base, his mastery of the metaphor, his beautiful sentences. His best stories read like true-life fairytales.

I set my sights on becoming his colleague. Unfortunately, when I finally got the chance to join Esquire, it was to write “The Game,” which Charlie had left to write features for Esquire and elsewhere and to join the staff of his hometown Boston Globe.

Let me tell you something: Nothing made my insides turn more quickly to mush than the idea that I was filling the space formerly occupied by Charlie Pierce. I’m the one other person on earth who knows how Ryan Minor felt.

More happily, Charlie and I have since become friends. This past fall, we sat in a bar in New York City called Jimmy’s Corner and watched Roy Halladay no-hit the Cincinnati Reds. We shouted over the jukebox and laughed and drank whiskey, and I couldn’t help remembering how I had once been a young man who had studied the words written by the man beside me, and now here we both were, drunk in Jimmy’s Corner. Roy Halladay was the least perfect thing about that night.

With pride and pleasure, I’d like to introduce my friend, Mr. Charles. P. Pierce:

Wednesday, February 23, 2011


Jeff Pearlman is a columnist for and the author of four sports biographies, including the best-selling Boys Will Be Boys: The Glory Days and Party Nights of the Dallas Cowboys Dynasty.

He was also, back in 1999 or 2000, watching BP from the first-base side at Veterans Stadium before an ordinary afternoon game between the Toronto Blue Jays and Philadelphia Phillies.

At the time, he was one of the youngest writers at Sports Illustrated; I was a beat writer for National Post. Jeff was the guy I aspired to be. For maybe twenty minutes, I stood with my back to the cage—rookie mistake—and asked him many, many questions about how to become a magazine writer. He was very kind and patient in his answers. They were helpful and inspiring. He wore a red hat. The sky was blue. Jeff doesn’t remember our conversation—I checked—but I remember it very well.

Whenever a young writer asks me about my work and how I do it, I think about how generous Jeff was with me that afternoon at the Vet.

And now here he is again, all these years later, still answering my questions.

My thanks, then and now, to Jeff Pearlman.

Wednesday, February 9, 2011


Wright Thompson is a friend of mine. We met at the Masters five or six years ago. There was a dinner for golf writers, and I’d never been to anything like that before. I wore shorts and a loud shirt. I got out of my car in the parking lot and saw all these guys in suits. Oh, shit, I thought. I walked in, and there was one other dude in shorts and a loud shirt. I started walking up to him and he started smiling, and I said something like, “You and me, we’re hanging out tonight.” That dude was Wright. And so we did.

Wright lives in Mississippi. He made his bones at newspapers, including the Kansas City Star, and now writes features for Whenever they land, they are centerpieces. He appears annually in Best American Sports Writing. He writes long and often personally, and he lays his heart out there, which is a rare thing these cynical days. For a lot of us, it can feel like too much of a risk.

But I love Wright because he takes risks. He takes chances. He’s wide open. The other day, I sent him these five questions about writing. (He’d emailed to say how much he thought of Gene Weingarten’s responses, and I saw my opening.) Hours later, Wright sent back 2,500 honest, beautiful, purposeful words. One more time, he’d served up that big bleeding southern cheeseburger heart of his, and I want to thank him for that, sincerely. I’m lucky to call him a friend, and I’m lucky to be able to read him and feel like he’s kicked my ass again. Love and the occasional beating: I’ll always be glad we were both wearing shorts and loud shirts that night in Augusta.

Ladies and gentlemen, Mr. Wright Thompson:

Monday, February 7, 2011


Gene Weingarten is a columnist and humor writer for The Washington Post. He recently pulled the remarkable trick of winning two Pulitzer Prizes for Feature Writing—the only person to win twice in that category—in a three-year stretch. His first winning story, “Pearls Before Breakfast,” explored what would happen if a virtuoso violinist named Joshua Bell masqueraded as a street musician in the D.C. subway. (Virtually everybody except children ignored him.) The second, “Fatal Distraction,” was a heart-wrenching account of parents who accidentally killed their kids by leaving them in hot cars. He has written four books; his latest… well, you’ll see.

I’m thrilled that Gene—this award-winning journalist and kind soul who also sports a terrific mustache—agreed to be the first subject of Son of Bold Venture’s new feature, Five for Writing.

Thank you, Gene, very much. Enjoy, everybody.


A new feature will debut here at Son of Bold Venture later today: Five for Writing.

In it, I’ll email five questions to a great writer about his or her work and how they do it. I hope to include writers of all stripes: novelists, journalists, fabulists, and essayists, moralists and monsters. Some of them will be friends of mine; some of them will be strangers to all of us. I think that doing the interview by email will allow each writer to do what he or she does best. Keeping it to five questions, I hope, will keep things fresh and lively.

Also, having five questions means I can call it Five for Writing, betraying my semi-secret affection for hockey, and its major penalties for fisticuffs especially.