ESPN’s Bill Simmons periodically writes about gambling, whether it’s on sports he’s watching or trips to Las Vegas with his fantasy football buddies. So it seemed fitting that in the hours before Simmons’ high-profile new venture Grantland launched — with Dan Fierman as deputy editor and starring top players/Simmons allies like Chuck Klosterman and Malcolm Gladwell as consulting editors, managing a cast of top talent — other writers were laying odds and making bets on the site.

Dan Shanoff of Quickish was/is bullish: “I’ll set the over-under at an Atlantic.com-style 5 million unique visitors a month within just a month or two, doubling from there by football season.” Meanwhile, Deadspin’s Tommy Craggs, who nearly jumped ship to Grantland before falling out with ESPN management, is comparatively bearish in an interview with New York’s Will Leitch:

I have no doubt Grantland will be really, really good. There are way too many smart people involved for the site to be anything less. I think it’ll be great to the extent that it can keep Bristol at arm’s length. I’m pessimistic about that part, for obvious reasons…ESPN is a terrible company full of craven morons who would rather maintain an air of phony intramural bonhomie than hire someone like me.

Meanwhile, Craggs’s Deadspin colleague Barry Petchesky took a more humorous angle, setting odds on topics & titles for the site’s first published story. Here are a few of Deadspin’s best lines (in both senses of the word):

3/1 Podcast with Simmons and Klosterman on LeBron
4/1 Simmons on LeBron
5/1 Klosterman on LeBron
10/1 Gladwell has some sports hypothesis that’s completely unsupported by the data, but parroted for years as fact anyway
20/1 Jay Caspian Kang on gambling
10/1 Jay Caspian Kang on his own gambling
4/1 Dave Eggers referencing his “Real World” tryout as a way of validating Grantland cred
1/1 Katie Baker on her conflicting emotions about Plaxico Burress’s release from prison
3/1 Katie Baker on her conflicting emotions about Donnie Walsh’s release from the Knicks

Gambling is an enormous part of sports culture, but it’s a part that until recently, professional journalists largely left implicit and unaddressed. Despite resistance from respected writers like Dave Kindred, Simmons’s writer-as-fan perspective and the embrace of quasi-sports like poker by writers like Kang (and outlets like ESPN) helped change that. It’s that kind of shift in how we talk about sports, and what kinds of stories we tell, that Grantland’s trying to pull off again, by openly adopting a more thought-leading magazine tone, leavened with Simmons’s trademark humor.

As it turned out, at Grantland’s launch, site watchers got no gambling narratives, no Kang or Eggers or Gladwell. Nothing referencing the latest sports news. The two stories explicitly about sports — Esquire writer Chris Jones’s essay/memoir of covering baseball, leaving the beat, and returning to it, and Klosterman’s story of junior college basketball in 1988 North Dakota — are alternately personal and historical. They’re long-reads, stories inflected by sports as much as they’re about sports. (LeBron and a taste of on-deadline sports commentary did pop up a few hours later.)

Meanwhile, “Grantland’s Reality TV Fantasy League: The Complete Rules and Draft Results,” drafted by David Jacoby but conceived and executed together with Simmons, Kang, Joe House, Connor Schell, and Lane Brown, is all high-concept 21st-century-media catnip, adding all new levels of unreality to two already virtual genres. Each fantasy owner gets points, mostly for bad behavior by participants. The scoring system for Celebrity Rehab with Dr. Drew is fairly representative:

• Abusing a substance while in rehab: 20 points
• Making Dr. Drew cry: 25 points
• Mentioning comeback plans: 10 points
• Saying a child/spouse/girlfriend/boyfriend is “everything to me,” “my life,” and/or “my world”: 10 points
• Attempting to escape and failing: 30 points
• Attempting to escape and succeeding: 50 points
• Getting arrested and/or going back to rehab before airing of show’s finale: 100 points

Finally, there’s a meandering (but mostly charming) statement of purpose from Simmons. Between telling stories of his time as a TV comedy writer and explaining his vision of what he wants the site to be, Grantland’s new editor-in-chief reminds his readers that wherever there is real risk, there are no sure things:

I would love to tell you that this website will work, that we’ll entertain you five days a week and blend sports and pop culture successfully. The truth is, I don’t know for sure... We are still hiring people. We are still finding writers. We will eventually have a sports blog and a pop culture blog (launching next month), user comments (later this summer), a podcast network (ditto), a quarterly publication we’re doing with McSweeney’s (four a year, starting this winter), and who knows what else. You figure out what works, you figure out what doesn’t work, you keep moving. That’s the next nine months for us. Eventually, we will evolve into what we are. Whatever the hell that is.

I don’t quite know what that is either. Stepping away from immediate sports news seems like a smart move, especially if that gap can eventually be filled in by a bloggier blog with what’s sure to be an enthusiastic commenting community later on. It gives Simmons and his writers room to tell complex stories with a distinct perspective.

Most sports fans, for reasons relating to either fans or sports, seem to be able to dwell in both past and present. We’re deeply interested in older stories that give context to both our own memories and what we’re watching on our television sets in real-time. That historical breathing room contributed to the success of Simmons’s 30 for 30 documentary series and his best-selling Book of Basketball. He’s wise to follow that here.

As for reality TV fantasy leagues, I’m not the target audience, but just like ESPN broadening its broadcast scope to include poker, both reality TV and fantasy sports speak to the permeation of sports metaphors in our broader culture. As amateurs watching sports, we compete with each other for our own entertainment; as television watchers, we’re entertained by nominal amateurs competing among themselves.

In some ways, athletes were the first reality media stars, larger-than-life personalities whose personal quirks are frequently as outsized as their talents, who compete for our attention but who are in principle pretending to be no one other than themselves.

But maybe even this cultural-symptomatic analysis is too premature. As Petchesky writes at Deadspin, “the eyes of the sports world [are] eagerly waiting to praise and/or bury the site based on a small sample size.” A reality TV fantasy league can be read with high seriousness, but at the same time, it’s a goof, a game — something to crack up a small circle of close friends.

Simmons and company are inviting their readers to treat them as both serious cultural commentators and a gang of fans trying to make each other laugh. And if you want to eavesdrop and laugh along, great. If not, start up your own fantasy league. Those can be hard extremes to reconcile. More than trying to simultaneously make fans of sports and pop culture equally happy, this balance of import and intimacy may be the balancing act that will prove toughest for Grantland to pull off.