10 Questions with Sports Illustrated's Jack Dickey


Raised in Guilford, Connecticut, a suburb outside of New Haven, Jack Dickey came to the Big Apple to attend Columbia University. Jack started as a staff writer for Deadspin, then moved onto TIME and is now at Sports Illustrated, writing about sports, politics and everything in between. In this interview, we learn about his views on the news industry and the Guild, his interests outside of work and his level of (dis)satisfaction with the Mets. 

1. If you weren't working in journalism, what would you be doing?

I’d be general manager of the Mets. Or a federal prosecutor. And I’d bring charges against the Mets for all the harm they’ve inflicted.


2. Who's your favorite journalist or writer - living or dead?

I’ll give you one of each—Tom Wolfe and Edith Wharton. They understood and chronicled society better than anyone else.


3. What could the news business use more of?

Humor. So much in 2017 is grim, and it is indeed the press’ task to call attention to all that. But unbroken darkness only scares people off.


4. Less of?

Unearned authoritativeness. We can’t predict the future, and we don’t know what’s inside the heads of most people. Punditry has its place, but cocky soothsaying is something else entirely. Unfortunately, people seem to click on it.


5. Name a piece of journalism that moved you most profoundly.

There are so many, including plenty you’ll find in the pages of Sports Illustrated (subscribe today). My brilliant colleague Chris Ballard alone has written a handful that made me cry. But what’s coming to mind at the moment are two pieces of journalism from Guantánamo: Pardiss Kebriaei’s “Life After Guantánamo” from the April 2015 Harper’s, and “Prisoner 760,” Holly Williams’ interview of Mohamedou Slahi, from 60 Minutes this past March. Infuriating, heartbreaking, required reading.


6. What makes you hopeful about the future of journalism?

Technology has made it easy to find fine work from all over the geographic and intellectual map.


7. What worries you?

Technology has made it so that our employers don’t make nearly as much money as they used to.


8. When you're not reporting, what occupies your time?

I like to watch sports and read, which is more or less what I do professionally, and I like to cook, which isn’t.


9. Why is being in the Guild better than not being in the Guild?

So many outside forces are warping journalism, demanding outlets produce work that is less thorough, scrupulous and thoughtful than it should be. (Or face the consequences.) But through contract enforcement and general pro-journalist advocacy, the Guild provides a check on the chaos. 


10. If you could give someone starting out in journalism one piece of advice what would it be?

Think. In sports, a large pool of journalists is often stuck working with a small pool of facts, stats and quotes. A novel idea or framing can make a would-be snoozer sing. Oh, and organize.

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