[3] Simmons envisioned a platform that allowed for in-depth analysis and storytelling, akin to traditional magazine journalism but adapted for the digital age.

Despite being backed by ESPN, the site operated with considerable autonomy, allowing its writers to explore a wide range of topics and voices.

[8] On October 30, 2015, ESPN officially announced the shut down of Grantland: "After careful consideration, we have decided to direct our time and energy going forward to projects that we believe will have a broader and more significant impact across our enterprise.

Huffington Post writer Justin Block writes, "In an era ruled by bite-sized content and dumbed-down click-bait journalism, Grantland's defining characteristic came at odds with sustainable finances.

"[11] Grantland's articles were often long form and usually not instant but measured reactionary pieces, a trend not common in today's media landscape.

[12] Grantland received 6 million unique visitors in March 2015, a number that some people believed could not support a staff of 50 writers, editors and IT personnel.

Some have concluded that Grantland's closure represents a trend in today's media business that unless you are one of the biggest web properties or smallest one-person "micro sites" it's tough to be economically viable.

[20] An article written by Caleb Hannan and published on the Grantland website in January 2014 received considerable criticism from the transgender community.

[26] The site featured contributions from Simmons alongside other sports and pop-culture writers and podcasters including: Holly Anderson, Mallory Rubin, Katie Baker, Bill Barnwell, Rembert Browne, Andy Greenwald, Bryan Curtis, Kirk Goldsberry, Steven Hyden, Michael Weinreb, David Jacoby, Jonah Keri, Chuck Klosterman, Molly Lambert, Jane Leavy, Mark Lisanti, Zach Lowe, Robert Mays, Davy Rothbart, Sean McIndoe, Brian Phillips, Charles P. Pierce, former NBA player Jalen Rose, Shea Serrano, Andrew Sharp, Louisa Thomas and Mark Titus.

Former contributors include Men in Blazers duo Roger Bennett and Michael Davies, Spike Friedman, Tom Bissell, Lane Brown, Jason Concepcion, author Dave Eggers, author Malcolm Gladwell, Justin Halpern, Mark Harris, Jay Caspian Kang, screenwriter of the movie Rounders Brian Koppelman, Juliet Litman, Pulitzer Prize-winning journalist Wesley Morris, Chris Ryan, MacArthur Award-winning novelist Colson Whitehead, former sportswriter and television producer Nell Scovell, and Emily Yoshida.