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“A Descent Into Madness”: An Oral History of the Fantasy Football Draft That Almost Tore Apart The Ringer

Multiple restarts. No pizza. Cries for justice and mercy. How an effort to foster community in the workplace turned into a 38-hour-and-46-minute death march to hell.

A man sitting in the Ringer office under a green Ringer logo The Ringer

On Tuesday, September 5, several employees of The Ringer attempted to hold a fantasy football draft, the first time staffers had attempted to organize a football league since the site’s 2016 launch. It was a phenomenal failure, an experience universally panned as the worst draft any participant has ever been a part of. We spoke to those involved so that the world can know the true story of this fantasy football disaster.

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Mallory Rubin, deputy editor: From start to finish—actually, I can’t say from start to finish, because we haven’t fucking finished—but from start to wherever-the-hell-we-are-now, it has been a debacle. A debacle of unrivaled proportions.

Riley McAtee, assistant editor: I never expected it to be this bad. It was a fucking nightmare.

Jason Concepcion, staff writer: It was a complete and utter debacle. This is unprecedented shit.

Danny Kelly, staff writer: People were just in tatters. It was like walking through a house the night after a party, when everybody’s just totally hungover, on the couches, lying on chairs and shit.

Jason Gallagher, multimedia editor: I would imagine this is what it was like being on the set of Apocalypse Now: “Oh shit. This is a nightmarish experience, but years later, I'll definitely brag about this to my grandkids.”

Sean Fennessey, editor-in-chief: It was the first and only time I've had real concerns about the future of The Ringer.

Robert Mays, staff writer (via Twitter): The Ringer’s fantasy football draft is the most calamitous occasion in the game’s history. I’ve never felt worse about our chances.

Katie Baker, staff writer: I’ve really never felt closer to my colleagues.

Part I: A Reluctant Commissioner

Unbeknownst to many staffers, the drama started long before draft night. While many of the complaints about the draft were criticisms of the decision-making and leadership of cocommissioners Sean Yoo and Matt Gothard, both associate producers on The Ringer’s video team, Yoo and Gothard rose to power only after a plot by multiple staffers to avoid the responsibility of controlling the league.

McAtee: I’d run the Grantland fantasy football league back in the day. Part of the reason we didn’t have a fantasy football league last year is because I just refused to be the commissioner, and nobody else stepped up. This year I wanted to step up and make sure I could pressure somebody else into being commish. Basically, the few people who had been hired more recently than I was.

Haley O’Shaughnessy, editorial assistant: Something told me, stay away from it. I knew if I messed something like this up, job security was at stake. I mean, I just got hired.

Paolo Uggetti, editorial assistant: None of us wanted to be commissioner. But as a last-minute Hail Mary, we called up Sean and asked him if he would do it. We were all encouraging it.

O’Shaughnessy: I have the receipts. We all agreed to this. I brought it up to Sean Yoo.

Sean Yoo, associate producer: They told me it was because they work super-close to the interns, and they didn’t want the interns to feel left out.

O’Shaughnessy: We had to plant the idea in his head. Have you seen Inception?

Yoo: I accepted it half-heartedly but with a lot of optimism.

Part II: The Pizza That Never Was

The first sign of discord came in The Ringer’s Los Angeles offices. Some league participants expected there to be an in-person gathering with food—specifically, pizza.

Gallagher: The draft was fucked before it even started.

Yoo: There wasn’t a lot of talk in the fantasy football channel, so I thought, OK, everybody’s going to be drafting at their respective homes.

Rubin: I learn there’s no gathering planned, no pizza ordered, no anything at all.

Gallagher: Mallory is legit, no joke, pacing. Pretty pissed off. She’s saying, “I can’t believe they left. I can’t believe they didn’t order pizza.” She’s really upset about the fucking pizza. She’s saying, “It is an utter failure. A fireable offense. You suck as the commissioner if you do not order pizza for the people drafting.”

Yoo: Mal was the only person complaining heavily about the pizza not being there. And it’s strange for Mal to complain. The last draft I had at The Ringer was the fantasy baseball draft, and there was no pizza at that draft.

Rubin: For the Ringer baseball draft, we gathered in the conference room. The spirit of community was palpable, and it was beautiful. This had none of that.

Claire McNear, staff writer: Mal is scary when she’s denied pizza.

Part III: The Draft Begins

That so many staffers had asked to join the league led to two problems: Leagues can’t have 20-plus teams, and it’s almost impossible to find a night when 20-plus people can draft simultaneously. Both problems appeared to be solved when league members partnered up, limiting the number of teams to 12 and ensuring that at least one comanager of every team could make the draft. However, this added an unforeseen difficulty.

Megan Schuster, researcher: I made my first overall pick. I took David Johnson. I think Riley and Sean [Fennessey] took Le’Veon Bell, and everything seemed to be going smoothly. And then all of a sudden Claire couldn’t draft, and Ryan [O’Hanlon] couldn’t draft, and nobody could figure out why.

O’Shaughnessy: I was ready to make fun of them so much. But it just kept happening.

McNear: I’ve never done fantasy football before, and I was worried about that. And then I opened up [the draft engine] and I couldn’t click on anything.

Schuster: Claire was asking where the draft button even was. I thought she just hadn’t used that thing before.

Mays: Whoever signed up for the Yahoo! team was the only one with drafting privileges. I have never done a draft with co-owners. We should have known you have to be the one who signed up to draft. That’s information you have to know going into the situation.

Yoo: I wonder if I should have known that.

Kelly, McNear’s co-owner: I was doing a live podcast in Seattle. Two minutes before I went on stage, I got a text from Mays saying Claire can’t draft for our team, and I have to send over my password and login.

McNear: I won’t tell you what his password is, but it was very funny. It was a very illuminating journey into Danny’s head.

Kelly: That’s my login and password for all my important financial data. Claire and Mays could probably get into my bank account. But on a fantasy football team, you need complete trust.

Bank account, maybe. But they could not get into Kelly’s Yahoo! account.

McNear: Yahoo! has crazy security. They really don’t want you to mess with anybody’s fantasy team. Yahoo! is asking me for select digits of some phone number of Danny’s. Robert texted me [Danny’s] cell number, but Yahoo! wanted a different number. It was a catastrophe. Fifteen different solutions were offered, and none of them worked.

The league was burning, but Yoo was occupied.

Yoo: During the draft I was in the middle of making dinner, which caused a little bit of extra stress, hearing that people couldn’t draft.

Yoo had created a few other problems with the league.

McAtee: There were a bunch of other weird rules. Like 0.75 points per reception, and you get double points for a 50-yard field goal, for no real reason.

Jason Cahill, executive producer, Talk the Thrones: What league has 0.75 PPR? We just should have revolted right then and there.

Rubin: I was very distressed to see we had a 90-second clock. I need an efficient draft. A 45-second, maybe-60-second clock.

After a few rounds, Yoo made the decision to restart the draft. However, the problem was not resolved. McNear and O’Hanlon still did not have access to the draft.

Ryan O’Hanlon, senior editor: Automatically drafting Jay Ajayi twice was like being forced to watch my own birth on a loop—except, when the doctor turns around and shows the baby, it’s not me. It’s a gargoyle.

Mays: We could have paused it and gotten the info from Danny and Collin [Orcutt, O’Hanlon’s co-owner]. I had just done a draft. I know pausing the draft is an option. But apparently Sean did not think that was an option.

Part IV: New Plan, New Problems

After two unsuccessful tries to draft using Yahoo!’s draft engine, Yoo decided to attempt the draft for a third time—this time, via email.

McAtee: We could’ve probably come to a consensus that the email draft was the right solution a little sooner. I know Mal suggested it a few days ago.

Rubin: I want the record to state that I proposed an email draft initially. Not because it’s ideal; it certainly isn’t. It drags on for a long time, you never know when someone is going to make a pick, if people are in meetings. The time zones become a problem. But we have a lot of people in the league. I knew it was going to be problematic for people to agree on a draft time. People laughed! People called me a fool. And look, we ended up here.

It was the best solution, but added work for the commissioner.

Yoo: I was opposed to the email draft at first because it meant I would have to input all the picks into Yahoo!’s system.

The new draft format was also a problem for one owner, Rubie Edmondson, who does not have a co-owner. She was attending the U.S. Open on draft night.

Rubie Edmondson, social media and engagement manager: I had been using the Yahoo! fantasy app and had about 8 percent battery left by the time the draft actually started. I was just hoping to make it though the initial draft. But I had my preferred players set up, so I was ready for autodraft. Then I got the message that we were going to email draft, and my phone died.

The computer would have continued selecting Edmondson’s prelisted players if the league had continued drafting via Yahoo! But after the switch was made to email, the draft reached her spot and screeched to a halt.

Concepcion: I think one of my favorite moments of the night was when Katie Baker tweeted at Rubie’s husband to get her to charge her phone.

That was incredible. Iconic stuff.

Edmondson ended up using her husband’s phone to send emails for a few picks.

Edmondson: I just wanted to watch tennis.

Part V: Chaos Reigns

Draft progress was nonexistent. Ninety minutes into the email draft, nine picks had been made. The league burned.

Concepcion: I checked Slack and found what appeared to be a remake of Lord of the Flies. I enjoyed it quite a bit. It was amazing. The Slack was a descent into madness, into chaos, the likes of which we have never seen at The Ringer.

Yoo: Each chat message got progressively angrier to the point of “Fire Sean as commissioner,” “Fire Sean from The Ringer,” and that’s when I realized things had gotten out of hand.

Mays: Everyone else was like “Oh, this is hilarious! It’s so great!” I was like: This is the week of the NFL season. I’ve written more than I could possibly imagine. My brain is just a ridiculous radioactive muck. There’s no way I should be up doing this right now.

Uggetti: It started out hilariously bad. But then it got more somber than anything.

Cahill: This draft experience has ruined fantasy sports for me. It will forever be joyless. We're hours from kickoff and I'm just … sad. I have suffered a loss. I am a broken man.

McAtee: Both the Slack channel was blowing up and the Yahoo! chat was blowing up, but not everybody was in both. I was like, “Oh my god, this is just a mess.” There are so many moving parts here. And none of them are in sync.

Rubin: It was hard to feel like we were having one conversation. Some people weren’t reachable at all.

Fennessey (during the draft, via Slack): Is this a social experiment?

Part VI: Mallory’s Meltdown

Emotions ran high for many Tuesday night. But every person interviewed agreed that nobody got madder than Mallory Rubin.

Gallagher: Mallory is one of the nicest, sweetest people. She’s always hugging people, telling people they look great.

O’Shaughnessy: Oh my God, I have never seen that side of Mallory before.

Rubin: People who say that they’ve never seen that side of me clearly haven’t played fantasy sports with me before.

Mays: Mal likes silly things, but in a serious way. She does not consider fantasy football to be a silly thing. Mallory is the only person I’ve met who cares as much about fantasy football as I do.

Concepcion: I got a text from her like, “I hope there’s Wi-Fi on the bus to jail.” I think she meant she was going to go to jail for killing someone, but still wanted to finish the draft.

The principal target of Rubin’s ire was Yoo. This began with the pizza incident, and continued as various other cases of draft mismanagement unfolded.

Concepcion: Mallory Rubin is a fantasy sports savage. Mal is a very genial person. But when she senses weakness in the fantasy sports venue, she’ll cut a person’s throat. And I don’t think Sean Yoo was ready for that.

Gallagher: Mal was outwardly shitting on a coworker, which doesn’t happen very often.

Mays: She told Sean, don’t be surprised if your badge doesn’t work tomorrow, which, like, I don’t know what sort of firing power Mallory has, but I assume it’s a decent amount. For her to even say that in a joking manner was pretty incredible.

Rubin: Sean Yoo is the light of my life almost every day. He brings me tremendous joy. I have cherished getting to know him, as a person and a colleague. He’s one of the most creative and energetic people I’ve ever been around. He is really, truly part of the soul of The Ringer. Also, if you fuck with my fantasy league, you’re dead to me.

Rubin (during the draft, via Slack): You botched this draft. You forfeit the right to talk shit. For real. I'm responding to notes on a feature and will be with you shortly. I had 90 minutes to devote to this tonight, not 90 hours. This is chaos.

Rubin (via Slack, 30 seconds later): Lol I’m kidding pal.

But Yoo wasn’t Rubin’s only target.

Rubin: I was able to draft my own players. I was in control. I could have allowed the chaos to ensue unchecked. I could have allowed justice to be compromised. But I fought. I fought for my colleagues, the same ones who are getting on the phone with you today and attacking my character, I fought for them. And one of them repaid that kindness by fucking me.

After Rubin selected A.J. Green 10th overall in each of the two aborted drafts on Yahoo!, O’Hanlon swooped in and chose the Bengals wide receiver eighth overall in the definitive email draft.

Rubin: He took the player that I had clearly, CLEARLY shown an interest in building my team around.

O’Hanlon: If Mallory is upset with me, she should remember that she was the one who said, “Autodraft is bad for everyone. It corrupts the entire selection process.” By drafting A.J. Green, I like to think that I cleansed her soul.

Part VII: The Ongoing Aftermath

As the draft got worse and worse, everybody began to blame themselves.

McNear: I assumed it was my own incompetence at first.

Kelly: I was thinking this whole thing was my fault.

Edmondson: I was reading back through and I felt awful because I thought I fucked things up for everybody.

But now, the smoke has cleared. It is clear whose fault it was.

Yoo: If me leading the league is any sign of my leadership ability in the workplace ... I think it’s a sign I shouldn’t be leading.

But everybody seemed to be lenient.

Schuster: Circumstances were slightly out of his control, the whole not knowing comanagers could draft. The pizza thing was a little unforgivable.

McAtee: There needs to be a little understanding that this is a pretty monumental fuck-up, but part of it isn’t his fault. I think we need to buy Sean a T-shirt for all the stupid heat he’s taken over the last [38] hours.

Concepcion: Sean handled it with as much grace as a man who has totally failed can. I pity him.

Well, ALMOST everybody seems to be lenient.

Rubin: I don’t have any pity for him as a person.

The email draft turned out to be outrageously slow.

O’Shaughnessy: I don’t have the patience for something like this. I could understand how this would work for people in retirement, or on vacation, or something like that. If we had many months. But the games start Thursday. I don’t know if we’re going to make it.

Rubin: One thing about The Ringer’s fantasy football league is it’s full of Ringer employees. People who work for The Ringer have to make content for The Ringer. If everybody’s going to be in the draft for fucking 90 hours, that’s hard.

At 10:46 a.m. PT Thursday morning—38 hours and 46 minutes after The Ringer’s first fantasy football draft began, about eight hours before the beginning of the NFL season—the draft finished, with Schuster and comanager Chris Almeida’s selection of Miami Dolphin Jay Cutler.

But the work was not over, the scars have not healed—and the commissioner never provided pizza.

Rubin: When we finish this, guess who has to manually enter all the rosters. The guy who couldn’t get fucking pizza.