Fantasy Loser – Funny Punishments, Draft Ideas & Articles

The 5 Guys to Watch Out for in Your Fantasy League

FL MikeG

Sep 29, 2025, 4:01 PM ET • 5 min read

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As a fantasy commissioner, you know that managing big personalities is one of your top duties. It’s how you ensure that your commissioner’s powers are never in question, and the league is prospering. In the course of your tenure as a fantasy commissioner, you’re likely to encounter a few personalities that can make things as harmonious as a toxic office environment.

In order to make sure the commissioner is aware of their duties and to uphold the oath of all that is good and true in the world of fantasy sports, we’ve identified the five guys to watch out for in your fantasy league:

The Dissenter: We’ve all seen this guy, maybe as a commissioner you were this guy at one point… it’s the guy in your league who always has a complaint about something related to how you’re running the ship. Whether it’s questioning the scoring settings that have been in place for years on a Monday night in October when things didn’t go his way, or griping about how this year’s draft order was determined, this guy is a thorn in your side. You’ll have to make him feel heard to really placate him, and do your best to make sure his toxic aura doesn’t spread around.

-The Ghost: Some people don’t believe in ghosts, but they surely exist in fantasy leagues. This is the guy that seems to live on the fringe of fantasy society; a wild card that either is starting a hospital list of players by Week 5, or somehow looks like a rocket scientist with an auto drafted squad. When you need a key swing vote on a league issue, he’s nowhere to be found. Too busy with his kids, or his job, or his wife, or something else… but truly what is more important than being a fantasy owner? 1:1 communications and maybe even a good ole’ fashioned phone call is the only way to confirm this guy actually has a pulse.

-The Trade Guy: On one hand, this guy is a legend for keeping the league active by sending out trades and prompting decisions. On the other, he’s sending the most vile, trash offers the world has ever seen. We’re talking trades that can raise human rights alarms in some countries. He’ll spin a web of lies on how this trade is actually helping the other party more than him. The worst part is, when he is able to convince The Ghost on a trade by sheer annoyance and sending a carrier pigeon with his offer, it’ll send the league in disarray and give The Dissenter another reason to accuse you of being a totalitarian leader when it gets rightfully vetoed.

-The Troll: As you may have learned as a kid reading fairy tales, trolls take many forms. So does the fantasy troll. In truth, he’s some sort of sadist who’s takes pride in the league’s pain. He might be running the clock down to the last second during the draft just for funsies, or placing a crazy FAAB bid when he’s not even sniffing the playoff race; this guy lives to cause misery and mental anguish. Nevertheless, they are a treasure to the competitive nature that is fantasy sports, and some people will truly do anything to get an edge.

-The Punishment Pansy: Here at Fantasy Loser, we also call this guy our mortal enemy. When it comes time to face the music, he will do anything but. Maybe his parents never taught him any sense of responsibility or commitment, but he’s going to quit instead of doing the punishment your league agreed upon. Leaving a league is an ultimate shame move, and doing it to avoid a punishment is even worse. It’s a life lesson that can only be learned from fantasy misery, and the league is better off without someone who can’t keep their word.

Commissioner Gripes - ESPN MNF Scoring Glitch Week 2

FL MikeG

Sep 18, 2025, 9:04 PM ET • 3 min read

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As fantasy commissioners, we rely tremendously on the platforms that we run our leagues on. Think of it as a platform that a political candidate ties their big campaign to. There’s just certain associations with the commish who uses ESPN, Yahoo, Sleeper or wildly does things by hand; and likely in your league, there’s always somebody jonesing for a site host site switch.

Me personally? I’m an ESPN loyalist. I think their platform is comprehensive and modern (although the latest app update took some getting used to) and they’ve added some decent custom features over the years. As a commish in a few leagues, including one that just made the switch from Yahoo to ESPN, I’ve got to make sure a transition like that runs smoothly.

Converting all the points settings are one thing and something I used a laser focus that would make my high school math teacher a little bit proud. Now, when ESPN’s app craps the bed and decides that they’re going to glitch out and not count any points from Monday night’s barn burner between the Chargers and the Raiders on a Wednesday morning; in turn changing results in close games, everything goes on fire.

Raiders fantasy players like Geno Smith may have played close to zero, but in fantasy football every decimal point is pivotal.

It was a war zone in my league’s group chat Wednesday morning, as several alleged that they got screwed, or even daringly, that the commish played with the results. On my way to my day job, I had to look into these issues, and thank god as others on social media were having the same issue. Commissioner honor and integrity restored!

These apps just have to get it right, especially when precious fantasy points are at stake.

Fantasy Checklist: What Every Commish Needs Before the Draft Clock Starts

FL MikeG

Aug 12, 2025, 9:35 PM ET • 6 min read

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Hey Commish! So it’s time to get your league set up for the upcoming fantasy season... do you have all your ducks in a row? First and foremost, is your league ready to adopt a punishment this year? Check out Vegas Baby and the Calendar of Shame if you’re looking for inspiration.

Whether you're a Roger Goodell-esque leader who gets booed by the fans every time they make an announcement, a ruthless dictator who has the league firmly under their boot, or a populist commissioner who rules by consensus decisions, there are a few things you need to cross of your agenda at the beginning of the new season.

• Roll Call the League: Buehler…Buehler…. First order of business: make sure everyone is still down to play next year. As much as we all love fantasy, there’s always one guy who you’re not sure if he’s even alive based on their lack of transactions and group chat participation. Confirm if everyone is ready to run it back, or if it’s time to seek fresh blood.

• Lay the Foundation: Just like they do in the big leagues, convene with the fellow teams for an Owner’s Meeting of sorts to determine new rules, points, expansion, trade rules, FAAB budget, playoffs and such before the start of the new year. We suggest creating a Google Form to have the league vote and weigh in on new proposals that’ll be brought into the next iteration of your league.

• Set the Draft Time: Work with your league to find a time that works for everyone. With drafts taking place in the late summer, you’re going to likely need to work around some league members traveling or in different spots. Drafting from home is fun, but doing it from a bachelor party or tropical vacation could be LEGENDARY!

• Determine the Order: Luckily, your friends at Fantasy Loser have tons of ways you can determine your draft order for the new season. Some of our personal faves? A Flip Cup Tourney or a Milk Chugging Contest (get the Lactaid ready!). Or you can go with a fun, random graphic over 100YardRush.com, or get in touch with a real draft order pro like Frank the Tank via Cameo. If you’re boring, just let the platform randomly determine the order.

• Collect Dues: To ensure the fantasy strugglers aren’t delinquent on their dues, collect them before the draft. That way the guy that picks the wrong running back named Robinson in the first round doesn’t balk on his dues when they’ve made a comical error. Be flexible in terms of where you can accept payment, Venmo, Cash App, PayPal, Zelle or cold hard cash are all perfectly acceptable legal tender in the fantasy ecosystem. We don’t want to have the commissioner have to send out a few wise guys to collect dues at the end of the year if you catch my drift.

• Get Hype!: You’re the commissioner and you set the tone for the rest of your league. Sometimes, think of them as impressionable little children and you’re the parent trying to inspire them to do the right thing. Get the group chat fired up, spread some hype and cheer, and of course talk a little smack to stoke the flames of rivalry to get your loyal subjects ready to rock in the new year.

• Don’t Forget About Yourself: Being a fantasy commissioner can be a thankless job at times. No one appreciates all the behind-the-scenes BS you have to deal with sometimes. Make sure you take the time to prep for your own draft and show them that the commish is still the boss of this league. Nobody respects a last-place commissioner!