Technology

Remember that time Bill Simmons offered Tommy Craggs a job at Grantland?

Now both of the former website editors, spurned by their bosses, are in media free agency

Tommy Craggs was the executive editor of Gawker Media until Monday. Courtesy of Gawker Media

By Nik DeCosta-Klipa @NikDeCostaKlipa

July 20, 2015

2 minutes to read

Gawker Media executive editor Tommy Craggs resigned Monday after the company’s managing partnership voted to remove a post against the will of the editorial staff.

Craggs — previously the editor of the sports blog Deadspin — joins a host of sports media free agents — notably former Grantland editor-in-chief Bill Simmons, who all but hired Craggs just a few years ago.

Way back in 2011 — before podcasts were popular and Grantland.com was just a photo album of a family’s Bali vacation — Simmons tried to hire then-Deadspin editor Tommy Craggs for ESPN’s embryonic sports and pop culture website.

Deadspin reported that at a March 31 meeting with Simmons in Manhattan, “a formal offer was made, [Craggs] was going to accept the position and his last day at Deadspin would be June 1st.’’

But a week later Deadspin posted a scathing article on an ESPN Page 2 senior editor, which “incensed’’ the heads at ESPN, according to Deadspin, and put the offer letter on hold. A follow up meeting with ESPN vice president John Walsh was effectively sabotaged by then-Gawker editor A.J. Daulerio — in the form of a human telegram dressed in a gorilla suit, singing the SportsCenter theme.

Craggs did not end up getting the Grantland job. However, he doesn’t seem to hold it against Simmons.

In 2014, Craggs was complimentary of Simmons’ talent as a producer, editor, and curator of talent — even if he was less than fanatical of Simmons’ writing style:

He’s generally a force for good in Bristol. “30 For 30’’ is excellent—it’s what can happen when the best impulses of Bill Simmons align with the best impulses of ESPN—and Grantland, for all its faults, pays real money for writers I like a great deal to write about the things that interest them. It turns out Simmons has better, more catholic tastes than his own writing would suggest, which is the best thing you could ever say about an editor-in-chief

As editor-in-chief, Simmons led Grantland to critical acclaim, if not absolute financial success; while Craggs was promoted from Deadspin editor to the executive editor of all of Gawker Media.

Now, for the time being, they are both without jobs.

Simmons is waiting out the reminder of his contract, after John Skipper decided ESPN would not be renewing their deal. Craggs resigned Monday (along with Gawker.com editor Max Read) after the business managers of the site voted to remove a post — an anonymously-sourced post outing a Condé Nast executive who tried to hire a gay porn star for sex. Craggs had previously stated he would have to quit if the post was taken down, citing a breach of editorial independence.

Now the Craggs speculation begins, as it has for months now for Simmons.

The 15-year ESPNer was being chased by HBO, according to The Hollywood Reporter, but is said to have “several suitors.’’

With Simmons’ popularity, Sport Illustrated media reporter Richard Deitsch wrote, “Simmons could use his high profile to start his own multimedia platform with investment from private equity.’’

According to multiple reports, some Grantland editors/writers are looking to follow Simmons wherever he goes.

Maybe Craggs could join them.

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