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‘Humiliatingly Awesome:’ The Best (Worst?) Punishments for Fantasy Losers

Some fantasy leagues feature creative consequences for their last-place finishers.

In the world of fantasy sports, there is no greater triumph than winning a league championship. Claiming the top spot brings glory, a year of bragging rights and, if your league has a buy-in, a cash prize. But not every fantasy manager reaches that level of success—and the consequences for finishing in last place can range from humiliation to hypothermia.

While some leagues force losers to take the SAT or do a polar plunge, others have gotten a bit more creative. That’s how Kevin Ring ended up with a fluorescent pink Ford F150 that declares “I came in last place in my fantasy league” in giant white font and features unicorns, rainbows and stars.

Ring’s older brother Jeff and one of their fantasy buddies snuck the truck, which was originally burgundy, to a custom graphics shop while he was out of town. Jeff says he requested “a truck that a 6- or 7-year-old girl would be proud to drive.”

Their league, which Kevin had been trying to join for 19 years before he finally received admission, has 12 members and is wildly competitive. It’s also “extremely brutal to the person who comes in last place,” Jeff says. “Nobody can ever remember who won the title, but everybody certainly can remember who came in last.”

The 11 other members began plotting Kevin’s punishment in a secret group message about a month before the end of the season. They executed it over New Year’s Eve weekend thanks to a speedy job by Ronnie Hatem of Hatem Graphics, who pulled an all-nighter over the holiday to get the vinyl wrap done before Kevin got home.

The truck has already turned quite a few heads around the Rings’ hometown of Andover, Mass., and sparked some roasting on social media, but Kevin says driving the Lisa Frank-esque vehicle has been “humiliatingly awesome.”

“People are taking pictures, honking their horns. On the highway the other day I got stuck next to a school bus full of kids. They were all just laughing, pointing, thumbs up,” he says. “I feel like with fantasy most of the people out there either play or know somebody who plays, so they get it.”

Aaron Ladd, who finished at the bottom of a league made up of college friends, certainly gets it. Though he still swears by his team and shouts out Deebo Samuel for helping him pick up his only three wins of the season, he will be attending a JoJo Siwa concert alone in February as punishment for losing. Siwa is an 18-year-old pop star best known for her large hair bows, bedazzled clothing and massive fan base that includes 40 million TikTok followers

One of his friends, the commissioner of the league, faced him in the last-place game. The commissioner “tried to extend an olive branch” before the matchup by suggesting the two go to the show together, since it was inevitable that one of them was going to finish at the bottom.

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“I basically shunned that away, I was like, ‘Dude, I’m not going! You can have fun there,’” Ladd laughs. “I was so confident. I was like, ‘My team isn’t that bad. You’re going!’”

Unfortunately for Ladd, his team didn’t pull through. Now he has to drive two-and-a-half hours from Kansas City to Springfield, Mo., to watch Siwa. His league expensed his ticket, which he is “very thankful” for, but Ladd has to foot the rest of the bill.

“They said I gotta get the gas, and I’m thinking about getting a hotel room since it is such a drive away. You know, just make a whole evening out of it,” he says, adding that he might also get a shirt that says “last place in fantasy football” to wear to the concert.

There was a common denominator in Ladd and Ring’s futility: Both drafted Saquon Barkley in the first round. After the Giants’ running back went down with an ankle injury, so too did the losers’ chances of finishing atop their leagues. Ring took his brother’s advice, which he now regrets, and Ladd says he spread himself a little too thin by playing in three leagues (though he did win his family league).

An injured running back was also the downfall of Jonah Javad’s season. He drafted a strong team that included Christian McCaffrey, Lamar Jackson and Leonard Fournette but ultimately limped to last place. As a two-time defending champion, he says he got “a little too cocky” and predicted his own three-peat because he was so happy with his draft. In the end, “the fantasy football gods got the last laugh.”

He was given three punishment options but is leaning toward recording a karaoke album with songs picked by his fellow league members.

Piecing together a winning fantasy team is a task that may require as much luck as it does knowledge or analytical expertise, but Ring did offer some advice to players looking to avoid an unexpected truck makeover next year.

“Don’t trust your brother,” he says. “And don’t come in last.” 

@SI_Fantasy asked you to share some of your fantasy punishments. Here are some interesting ones: