A Trump Hat, The SAT, And Stand-Up: The Worst Fantasy Football Punishments

When's the last time you wrote with a pencil? Not a pen. Like with an actual No. 2 pencil? It was Week 7 when I really started asking myself that question. Let me explain.

In Week 7 of the 2015 NFL season, my fantasy football team lost its fifth straight game. I won't bore you with the injury reports, but Team Kessler was dropping down the standings. And our league, a group of my recently graduated friends from college, had a punishment: the person who finished last had to take the SAT ... again.

That would mean paying 50 bucks for a four-hour reminder that trigonometry is not like riding a bicycle.

Over the next few weeks — when I took a break from desperately scanning the waiver wire for useful players — I started to wonder if anyone playing in another fantasy football league might be dreading an even worse punishment.

And that’s what led me to Jackson Logie.

The Search Begins In A Comedy Club

"I think I took Tom Brady in the first round," Jackson tells me. "Maybe should have looked the running back route instead."

It's about 2:30 on a sunny Saturday afternoon, two months after the end of the 2015 fantasy season, when I meet Jackson Logie — or as one of his friends affectionately calls him, Jackson “The Loser” Logie.

Jackson is not a stand-up comic. He doesn’t even want to be one. But he does play fantasy football, and the last-place owner in his league was required to perform at an open mic.

Manhattan bars are typically bad places for radio interviews, but Jackson's hoping to calm his nerves a little bit — because in a couple hours he's scheduled to perform a stand-up comedy routine and ...

"I'm not gonna lie, I'm pretty nervous," Jackson says. "I'm not a generally funny person."

Jackson is not a stand-up comic. He doesn’t even want to be one. But he does play fantasy football, and the last-place owner in his league was required to perform at an open mic.

"The whole high school league, some other friends, friends of friends, co-workers, all the guys I work with are coming," Jackson says. "So there's definitely a worst-case scenario. I could barely sleep last night. I think the worst-case scenario is getting up there and just not remembering anything."

I leave Jackson — he says he's got notes to review and a couple more IPAs to drink before showtime — and take my spot at the venue, the basement of another bar. There's a mic set up in the middle of the room. The tables surrounding it are soon full.

Fifteen to 20 amateur comics are scheduled to perform, but almost everyone in the audience is here to see Jackson. He begins his routine by setting low expectations.

"This is going to be really, really painful for all of you, and it's going to suck," he says. "And to be honest, I really should have tried to get out of it. And I didn't. I feel badly about it. And I used to have this buddy back in college who tried to get out of everything. Absolutely everything."

Jackson tells the story of a college friend who wasn't prepared when his teaching assistant called on him.

"He immediately looks down and just goes, 'Phone call, I gotta take this. And he just books it out of the room," Jackson says. "Everyone's like, 'OK, whatever. That's obviously fake.'"

Jackson goes on for another couple minutes — before realizing enough is enough.

"That's all I've got," he tells the crowd. "Thank you guys for coming."

After the cheers die down, I pull Jackson aside for a quick debrief.

"I blacked out," he says. "I have no idea what I said."

Will he ever take the stage again?

"Absolutely not," Jackson says. "One-time thing. I did it. It's fun. It was awesome. And that's that."

It was awesome? That doesn't sound so bad.

So I started searching Twitter for things like "fantasy football punishment" and "miserable."

'Is Something Going On With Steve?'

That's how I found Steve Clark. He works as a school psychologist in New York State's North Country. He plays in a fantasy league with some of the kids he used to coach on the JV baseball team.

"It's pretty cutthroat," Steve says. "I thought I was going to out-smart all the young guys. But I can't keep up."

His league decided that the top three finishers would get the honor of creating a personalized punishment for the loser. So when Steve, one of the only Red Sox fans in town, came in last, he had an idea of where it was headed.

"I assumed I would have to wear Yankee gear," he says. "The political one stung a little more than that."

Turns out, supporting the Red Sox isn't the only thing that makes Steve unusual.

"I live in upstate New York, which is a tremendously conservative area of New York State," Steve says. "And there's not a whole lot of us Democrats up here. So they have this baseball hat that says 'Make America Great Again.' So they decided that my punishment was that I had to pose as a Donald Trump supporter. At first they thought I should have to wear this baseball hat in school, where I work. But then they decided, no, it might be better to have it as my profile picture on my Twitter account. "

And they told Steve that he had to make the picture look authentic — and not tell anyone why he’d done it. Otherwise, they'd make the punishment even worse. So ...

"I sat on my deck with my Make America Great Again hat. I was holding an American flag, a bottle of Jim Beam bourbon and one of my son's hunting rifles. My son took the picture and it went up on my Twitter account," Steve says. "All of the phone calls started coming. I have two daughters. They were calling me right away — 'What happened to dad? What's going on? We're concerned.'"

It got worse for the school psychologist.

"Our school principal got a message from our district superintendent who just said, 'Is something going on with Steve? He's our primary mental health service provider here in school, and he's posing with a rifle and a bottle of bourbon.'"

OK, putting your job at risk for fantasy football? A punishment can't get worse than that, right?

But then Steve finished the story.

"You know, slowly, over the time, they knew it was just a joke," he says. "But it was a lot of fun. We had a lot of fun with it."

Enough fun, apparently, that Steve is signed up for the coming season — though he’s been warned about a repeat performance.

"Basically what they said is, I better not finish last again. Because if I do, the punishment will be doubled. But I'm in a panic, 'cause I do not want to finish last again."

Which Is Worst?

Unaspiring comic Jackson "The Loser" Logie and his buddies already have their new punishment picked out: last place has to earn 10 bucks playing street music in Central Park. Neither Jackson – nor any of his friends — play instruments.

But I still wonder: is that — or wearing a Trump hat or the stand-up comedy routine — really worse than the SAT?

Because I never found out.

The waiver wire paid off, and Team Kessler finished in a respectable preantepenultimate place — that's "I studied my SAT vocab words" for fourth from last.

And I'd ask the actual loser of our league — a guy named Edward from California — but unlike Steve Clark or Jackson “The Loser” Logie, he chickened out of his punishment.

Which makes me think: the SAT must really be the worst…