There were times during my recent foray into daily fantasy sports when I had to suddenly stop whatever I was doing—brushing my teeth, talking to my children, working—because I urgently, desperately, feverishly needed to know who was starting in goal for the Calgary Flames.

I found myself constantly tapping my FanDuel app, checking and rechecking my roster for that night’s contest, researching power play percentages and injury reports. If I cultivated a lineup of that evening’s top NHL performers just right, my $1 entry fee had the potential for a $700 payout.

A 700-to-1 return is pretty spectacular, whether you are a mere fantasy sports nerd or a full-on degenerate gambler. The question of the moment, of course, is: When you play on a daily fantasy sports website like FanDuel or DraftKings, which one of those things are you?

New York Attorney General Eric Schneiderman says you’re a gambler, and he has ordered the fantasy sites to go dark within the state. The sites counter that their users are sophisticated sports aficionados (or, nerds), and they have been lawyering up in order to defend this worldview—and their profits.

Are daily fantasy sports gambling? As somebody who loves gambling but hates fantasy sports, I decided that I was as good an arbiter as any of this legal conundrum, though admittedly my “if I like it, it’s gambling; if I hate it, it’s fantasy” rubric was only slightly more scientific than a medieval floating-witch test.

Two months ago, I knew almost nothing about these sites. Then the ad blitz began. Between August and mid-October, according to The New York Times, DraftKings spent $107.5 million and FanDuel $85.8 million on TV ads that appeared about every 90 seconds on national TV.

At seemingly every commercial break, one or the other or both would show a cavalcade of back-slapping bros winning millions of dollars. The ads were as obnoxious as they were ubiquitous. Schlubby looking Everymen, some with disproportionately beautiful women on their arms, offered testimonials on how daily fantasy sports had changed their lives. Just sign up, pick your team and collect your winnings. You get paid the very next day! It’s that easy!

Then came the Times' reports of questionable ethics and potentially illegal business practices. New York State announced that it would investigate; the FBI did the same. Then the Nevada Gaming Board decided that daily fantasy sports sure smelled like gambling and ordered the sites to shut down or get gaming licenses, and other states started asking questions.

But the ads kept playing, taunting the government from atop the ramparts of a 2006 law that excluded fantasy sports (games of skill) from prohibitions against Internet gambling (games of chance). New York-based FanDuel posted a petition to “protect your right to keep playing fantasy sports,” and the sites responded to Nevada’s blackout by moving their big football championship tournaments from Las Vegas to San Diego.

I used my debit card to plunk down $25 on FanDuel and immediately started researching Finnish hockey players and NFL run-defense rankings. About three hours later, I had won my first big pot—not $700, but $2.50 for finishing 929th in an NHL tournament.

Surely you know how fantasy sports work? They have become an omnipresent part of society, the kind of thing you have to do—like tweeting or watching "Mad Men"—so you aren’t ostracized by friends or laid off from your job.

You choose a team of real-life players whose stats in their real-life games translate into fantasy points for your fantasy team. The fantasy team with the most points wins. Traditional fantasy leagues play over the course of an entire season, requiring a commitment to a set roster that you tend to lovingly like a garden.

Daily games, on the other hand, require zero commitment (on its site, FanDuel proudly quotes TechCrunch calling it the “one-night stand” of fantasy sports). You pick one set of players one night and a whole new set the next. In the case of NFL games, which are by far the most popular and lucrative, you rent players by the week.

The Rosetta Stone of modern fantasy was the league made famous in 1984 by Steve Wulf in Sports Illustrated and by Glen Waggoner’s "Rotisserie League Baseball," which was part textbook, part rulebook, all lark, from a group of literary types who had codified a point-scoring system. They named the league after the restaurant where they held their drafts and doused their champion with Yoo-Hoo. I was barely a teenager at the time, and I was fascinated with the idea of grown men collecting ballplayers in much the same way my friends and I flipped baseball cards in the basement.

But in the 30 years since Wulf and Waggoner introduced their silly little game, fantasy has evolved (devolved?) into more of a cultural obsession than cute diversion, closer to the rush of Red Bull than the juvenile satisfaction of Yoo-Hoo. Is there any more insidious social encounter than listening to somebody drone on about his fantasy draft? What fantasy does is carve fandom into tiny unrecognizable shards of statistics, where dirty uniforms and soft hands and quality at-bats have no value.

Daily games take that mercenary mentality to a whole new level: You are simply predicting which players will have a good game that day, based on some algorithm of their overall talent, their health, the quality of their own team and how they match up against their opponent. Even the weather and game time come into play. You are, in essence, becoming a hard-core handicapper.

You can’t merely pick the best players at each position, because a salary cap limits your spending, so the real “skill” is finding the best value among second- and third-tier players who don’t cost as much but are primed to have a big game. Anybody can draft Tom Brady, for example, but maybe you pick the Jets’ Ryan Fitzpatrick for a much-lower price, on a hunch that he will perform better than expected, which enables you to spend more on a top-flight running back or wide receiver. (It’s very complicated; ask the guy next to you at work, he’ll explain it to you for hours.)

(illustration by Matt Lubchansky)

Being particularly clueless about the NFL, I opted to focus more attention on the NHL. The interface of FanDuel was as easy as the commercials promised: A home-page “lobby” listed all the games available, from the high-volume tournaments with thousands of players and life-changing payoffs all the way down to $2 one-on-one games against other users with payoffs as low as $1.80. Entry fees ranged anywhere from $1 to $1,065.

I chose a $1 NHL tournament in which would pay $700 for first place, $400 for second, $200 for third, $100 for fourth and so on, in smaller and smaller increments, all the way down to a $2.50 prize for anybody finishing between 701st and 1,568th. With an overall field of 8,045 players at $1 apiece, FanDuel was taking in $8,045 in entry fees and paying out a total of $7,000, which means the site pocketed $1,045. And that was just one of thousands of contests available that day.

So I won only $2.50, but I was a winner, right? Where else can you finish 929th and feel like a winner? (Maybe in a marathon. But a marathon? Really?) This, I would learn over the next couple of weeks, is the genius of the FanDuel system — not just the siren song of huge payouts to a few big winners, but also the tiny amounts it doles out to thousands of people. When people feel like winners, they keep playing.

On a recent Saturday afternoon, there were 5,222 NFL game options for that weekend’s games. There was a $1 game called the “$200K Sun NFL Squib (Single Entry),” which had 229,885 spots competing for a $10,000 first prize. But you could still finish anywhere from 15,001th to 45,225th and win $2. After $200,000 in total payouts, FanDuel would pocket $29,885 in entry fees from this contest alone. There were 5,221 others.

For those looking for a little more skin, there was a contest called the “Bootleg,” open to 25 players with an entry fee of $5,300 each. It would pay $50,000 to the winner; $30,000 to second place; $20,000 for third; $15,000 for fourth; and $10,000 for fifth. The other 20 contestants would get nothing. After the payouts, the site would keep $7,500 for, in essence, having written a few lines of code and having risked no money of its own against the players.

By contrast, there were only 400-some hockey tournaments available that Saturday night, with pots ranging from $1,000 to $30,000. Since my winning debut, I had played 11 additional contests, paying a total of $18 in entry fees and finishing in the money twice for a grand winnings total of $5.80. I decided to pay $5 to join a game that offered $3,000 to the winner among 6,896 players. My goal was to finish higher than 1,296th, roughly in the top fifth, to claim at least $12.50 and basically break even over all.

I did not. In fact, only 856 of 6,896 players had lower scores than me. I was clearly not very good at this. (Let’s not even talk about the N.F.L. game in which I was 94,068th. Frickin’ Adrian Peterson.)

A few days later, I burned through my $25 allowance. Over 17 days, I had played 20 games, going 4-16 and winning $11.90 (which of course I also lost back). In the end, I was torn. FanDuel had both the disassociated stats mentality I hate about fantasy and the rush of easy money I love about gambling. (If nothing else, it gave me the opportunity to work the name Teemu Pulkkinen into a few conversations.) Where else can you entertain yourself on $25 for 17 days? Twenty-five dollars will buy you about 30 seconds of “entertainment” at a blackjack table or about two and half minutes at the racetrack. In New York City, $25 will get you into a movie, but it won’t cover the popcorn and soda, and Ben Affleck ain’t giving you a nickel back even if you’re one of the 949 people who enjoyed it.

Then again, I was playing the very low end of what FanDuel had to offer. What about those schlubby Everymen, guys who think they know everything about sports, playing for hundreds or even thousands of dollars, with their banking apps and their fantasy apps side by side on their phones? Are they looking at daily games as a diversion or an obsession? Once you lose $1,000 in one swing of the bat, it’s all too tempting to think you can, and will, win it back on another. That, friends, is gambling.

I sought the counsel of the journalist and author Daniel Okrent, who not only is the creator and founder of the original Rotisserie League, but also wrote a book on Prohibition, which makes him something of an expert on things people like to do but are, alas, illegal.

“It's definitely gambling,” Okrent said of the daily games. “Betting on thoroughbreds takes skill, too, but no one would argue that it isn't gambling. If it's to continue, it should be regulated and taxed, with the state getting its fair share. And I would, of course, be grateful for a nickel or two myself.”

Who came up with this so-called division between games of “skill” and games of “chance” anyway, as if those two things are mutually exclusive? Athletes themselves live by the proverb that it’s better to be lucky than good, and it’s true: The ‘86 Mets were an incredibly skilled team, but damned if they didn’t need the hand of God to poke Mookie’s grounder through Buckner’s legs. Let’s put sports at 92 percent skill, 8 percent luck.

In the casino, a consistent system and knowledge of the probabilities can increase your chances of winning, but you still can’t dictate what card will fall next. I’m going to put blackjack at 37 percent skill, 63 percent chance, for example, and poker at the reverse. Even craps — the literal “roll of the dice,” the very expression Vin Scully used to describe Kirk Gibson’s miraculous at-bat in the ‘88 World Series—has certain probabilities that players can work in their favor.

So what will the final breakdown be for daily fantasy sports? 70-30? 10-90? 50-50? Will the premise that they are knowledge-driven contests played by peers on a level playing field survive closer examination? Or does laying out a small sum of money in the hope of winning a large sum of money based on events that are ultimately out of your control fall under even the loosest definition of gambling? All I can say is: Good luck to the very skilled lawyers, lawmakers and judges who will have to decide.

Illustrations by Matt Lubchansky

David Vecsey is a writer and an editor; you can follow him on Twitter at @davidsvecsey.