Where does the ESPN-Bill Simmons relationship go from here?

Despite working for the most establishment brand in sports media, ESPN commentator and Grantland editor-in-chief Bill Simmons has always positioned himself as an outsider. You saw that last September when he dared his management to discipline him for comments he made about Roger Goodell, making an offer his company could not refuse when they suspended him for three weeks.

I’ve always believed there would be great personal appeal for Simmons to forge a go as an independent entity. But as I’ve written before, here is the simple truth: No other entity affords Simmons more resources and distribution for his work. Outside of Turner, no other entity has as many tangible connections to the NBA. And Simmons has great loyalty and fondness for the people he has hired at Grantland and his colleagues at ESPN Films. 

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That’s the backdrop for one of the great parlor games in the sports media for 2015: Will Simmons re-sign with ESPN? But maybe we should be looking at it in reverse: What is ESPN’s interest in re-signing Simmons when his contract expires later this year? Last week I tracked down ESPN president John Skipper and asked him to classify his company’s interest. I’m fairly certain these are his first public comments on the matter. 

“My interest is high in re-signing Bill,” Skipper said. “We like Bill. He has done good work for us. We continue to have a good collaboration, and I am anxious to have some discussions with Bill to see if we can continue to do things that work for ESPN.”

Asked how he would classify the odds of re-signing Simmons, Skipper said, “I would say it is like being on a high hilltop in Scotland and tough to see too far into the distance.”

Skipper did not say specifically when negotiations would begin -- Simmons has a longtime agent so it’s likely Skipper will talk with Simmons and his reps -- but he did praise the work Simmons has done and called him a personal friend. 

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“We are thrilled with Grantland and we are thrilled with Bill’s contribution to 30 for 30,” Skipper said. “The Grantland Basketball Hour is great. We get a lot of value of Mr. Simmons. He and I are personal friends and before too long, we will have discussions."

If Simmons does re-sign, it poses the question what would be his next evolution as a content creator?

“That is a really good question, the seminal question,” Skipper said. “Every time I have a discussion with Bill I start with: ‘Bill, what do you want to do next?’ I have not had that conversation with him recently but I will tell you that will be how I will start our conversation.”

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SI.com examines some of the week's top media stories.

1. TNT sideline reporter Craig Sager made an appearance during the network’s NBA All-Star Game (he interviewed Knicks forward Carmelo Anthony) on Sunday and said he hoped to return to full-time as early as next month. It was his first appearance on TV since his battle with leukemia last spring. “It’s something I’ve really missed,” Sager said. “It’s nice to be here in Florida (Orlando) but it was a rough price to pay. I think I am on the road back and I am looking forward to getting healthy and being there in March and April. 

1a. Turner said its coverage of the All-Star Game drew 7.2 million total viewers, down from last year’s 7.5 million viewers. The network’s All-Star Saturday Night generated averaged 6.1 million total viewers, which was up from 5.7 million in 2014.

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​2. The NFL Network will begin its 11th year of covering the NFL Scouting Combine and this year’s coverage is immense. The network said it will air 45 live hours from Indianapolis beginning Wednesday at 2 p.m. ET with the Scouting Combine press conferences from Lucas Oil Stadium. Coverage of the on-field workouts begins Friday with the offensive linemen and tight ends; the running backs, quarterbacks and wide receivers go Saturday; linebackers and defensive linemen work on Sunday, and defensive backs go Monday. Coverage of workouts begins each day at 9 a.m. ET. The network said it will use 26 analysts, hosts, and reporters from Indy including free-agent running back Chris Johnson, who owns the combine record in the 40 with a 4.24 in 2007.

2a. One new NFL Network feature this year is the use of comparative analytics technology. The network will have access to measurements, times, and reps for every player who has participated in the combine since 2003.

2b. NFL Network host Rich Eisen will once again run a 40-yard dash in his trademark suit. This year’s “Run Rich Run” will benefit the NFL Play 60 relationship with St. Jude Children’s Research Hospital. (For more information, fans can go here).

3. Skipper said he was pleased with the opening pieces from TheUndefeated.com, ESPN’s upcoming site focused on sports, race and culture. The site is set to launch later this year. “I would call it a taste or sneak preview, not a soft launch,” Skipper said. “The fact of the matter is we have begun to hire people who are talented and prolific and want to do things. The Jesse Washington piece on Charles Barkley, I am thrilled with it. It is a fabulous piece. We decided this piece was so good and emblematic of what we will be doing with the Undefeated that we [ran it now] so we thought lets give people a little sneak preview.”

3a. ESPN’s coverage of the ICC Cricket World Cup 2015 (February 13-March 28) is an on-demand play as the network is selling an online subscription package for $99.99 (Viewers can live stream the matches via the web and mobile). Here’s what Skipper said he’s hoping to learn from selling a sports package directly to consumers: 

“The main thing I am interested in is looking at our ability to create a site, an application, a mechanism that works and can go direct to consumer,” he said.  “We will get some experience how to market it, how to build, how to deliver it. That to me is the measure of success here, that we were able to pull this off. We did it pretty quickly and I think it will work. But of course we care about how many people sign up. We will do well with it but the only question is how well we will do.”

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​4. The late University of North Carolina basketball coach Dean Smith will be the subject of a one-hour Showtime Sports documentary titled “Dean Smith,” premiering on March 25 at 9 p.m. ET/PT on Showtime. The doc will be co-produced by Showtime Sports and Ross Greenburg Productions and directed and edited by George Roy. Greenburg and Roy have had great success as doc collaborators, so this has promise. Michael Jordan will be one of the featured voices in the piece. 

5. The NFL Network and Red Zone host Scott Hanson has been hired to serve as the blow-by-blow announcer for Spike TV’s “Premier Boxing Champions” series. The first  event will take place on March 13 at 9 p.m. ET from the Citizens Bank Arena in Ontario, CA.