The 5 Best Sports Stories Ever Written

I have a confession.

It’s tough for me to share this publicly, but for as long as I can remember, I’ve been obsessed with sports journalism.

I know, I’m not proud of it & I get it if you want to cut off ties now.

But, if you want to stick around… it’s raining & I’m in an old-school mood.

Plus, I haven’t written on here in forever & I know how important my sporadic, ill-defined, and poorly proofread newsletter is to you, so you’re super welcome.

I want to share a list of the greatest sports pieces to ever appear in a magazine (or newspaper). Some old, some more recent, all of them are old school by the very nature of the fact that they’re written articles created by humans.

They don’t do that anymore unfortunately.

How can you not be romantic about (the widespread immigrant appeal) baseball?

One Line TLDR: This NYT op-ed from 2012 takes the American themes famously ingrained in our national pastime and offers a beautifully fresh & personal twist.

Why I Love it: Yes, author Colum McCann agrees, baseball is American. Not just in the apple pie and Chevy way, but a game that means just as much (if not more) to so many immigrants, many of whom play in the MLB themselves. It’s a masterful lesson on challenging long-held wisdom, the role of identity in journalism, and how to make readers reconsider an old story (in this case, baseball belonging to stereotypical Americans) through a new lens.

If you haven’t read this next one & you consider yourself a fan of beautiful things, stop what you’re doing & read this story ASAP.

One Line TLDR: In 2006, David Foster Wallace wrote a piece on the magic of Roger Federer, describing in his exhaustive trademark word salads the utter beautiful insanity of a Federer performance.

Why I Love it: I, much like DFW (we’re essentially the same guy), have long felt a deep connection to Federer’s game. Not just through enjoying peak performance, but the actual movements he made during a match… as if he was so bored with his opponent he decided to choreograph his match to align with some higher frequency only heard by Fed. DFW’s deep descriptions of remarkable points + the ease with which he is able to share the emotion of each moment through prose rivaling Hemingway, penetrates so deep it has become my go-to reread in the post-Fed era.

I recently was sent this piece & loved it… the 1970 Sports Illustrated article on 65-year-old Karl Wallenda’s bone-chilling daredevil performance.

One Line TLDR: In front of 30,000 people, Wallenda walked for 20 minutes and took 616 steps across a wire less than 2 inches in diameter over Tallulah Gorge, 750 ft above ground. And he also stood on his head… twice.

Why I Love it: I’ve been a big fan of climbers like Alex Honnold and Jimmy Chin for years, as well as older daredevils like Evel Knievel. Especially for climbers like Honnold, I’m enthralled by the meditative state many of these extreme athletes enter during their most dangerous moments.

When I read about Wallenda, I remembered the documentary Man on Wire about French High-wire artist Philippe Petit’s unauthorized walk between the Twin Towers in 1974 (4 years before Wallenda died during a later stunt). The doc had always stuck with me & reading about Wallenda’s semi-insane ability to crack jokes and appear calm during the stunt reminded me of that oft-referenced state of serenity experienced by these daredevils. Author Mark Kram weaves both narrative and interview with expert tact throughout, resulting in the perfect combination of a source’s own story combined with well-timed thrust to keep pace.

It shouldn’t be a shock that death is a major topic of conversation — the entire Wallenda clan is involved in the family business in some capacity & they’ve had their share of fatalities — however, it is haunting to read those parts now knowing Wallenda had just a few more years before his luck ran out.

Sometimes you just find something you love, decide it’s the best, and refuse to hear any arguments to the contrary.

That’s how I feel about Gay Talese’s masterpiece Joe DiMaggio and the Silent Season of a Hero, published in the July 1966 issue of Esquire (the same year he’d write Frank Sinatra has a Cold, another piece of required reading for nerds)

Back to the task at hand…

One Line TLDR: Talese’s profile on DiMaggio post-Yankees & after the death of his ex-wife (still beloved) Marilyn Monroe paints a picture of tragedy, exposing the fleeting nature of fame, and the humanity inherent in all of us — even those deemed infallible.

Why I Love it: The piece is a winner from the start thanks to the Talese byline gracing the page. I don’t think I’m out of line saying he’s in the pantheon of magazine writers and a pioneer of the New Journalism movement. Add in DiMaggio, a fascinating figure who was not only an HOF player but was also Sinatra-level famous during his peak. During the period in which the article was written, DiiMaggio has basically lost everything he held dear (namely baseball & Monroe). The darkness of his fading star penetrates through the page and does a crafty job of allowing the reader to see the fallen hero for who he has become while simultaneously sympathizing with the man who felt forgotten and bitter.

As someone who not only grew up on Bill Simmons, but basically tried to rip off his writing style while I was the sports editor in college, I had to end the list with a piece from B.S.

One Line TLDR: Simmons recounts the feeling of experiencing sports fandom for the 1st time again through the eyes of his daughter (whom he photographs crying…)

Why I Love it: I could use this part to highlight some of Simmons’ more significant stylistic contributions to the ‘sports columns should be fun movement’ which he pioneered, but I’d rather just say that Simmons manages to work the phrase “stay off the pole,” and references to Michael Jackson and Forrest Gump… and as to be expected, none of these asides are necessary in the slightest. Bill please write again, we miss you.