Seven stories of fantasy heartbreak

The agony of the world's worst and best hobby

Right now, there’s a nation of confused fans wishing on any Monkey’s Paw they can find for sports to return. As that paw unfurls, it carries with it the reminder that sports brings fantasy playoffs, and fantasy playoffs bring pain.

Few other hobbies require the hours of research and tolerance for misery, where one bounce of a ball, or one missed tackle on a CJ Spiller catch in 2015, can haunt the poor losing sap forever.

We spend our free time trying to predict the performance of sports built on chaos, and yell and scream when this chaos ends up in a loss. Without any active sports, we’re missing out on this misery, but the memories never fade.

I asked you, the subscribers, to share some of your most memorable bad beats, and I added some color and research to find out who’s the unluckiest.

Using anger for educational purposes

Have you ever taught yourself a skill only to calibrate the appropriateness of your rage?

We’ll start with a brief trip down the humble author’s own miserable fantasy existence. As documented in my interview with Joseph Mamone, fantasy basketball is served best when done in a dynasty format. In it, you’re combining your basketball knowledge with the foresight and forward-thinking vision needed to compete multiple seasons into the future; a loss today might hurt, but not as much as the knowledge that you’ll never contend again.

Last year, I took on the league commissioner/supervillain in the semifinals of our playoffs, aiming to upset the then 19-1 behemoth beyond a ragtag squad of then-rookie Luka Doncic and Serbian prince Nikola Jokic.

Thanks to a combination of injury and scheduling luck, I managed to take an early lead, and just needed my steady shooting guard Klay Thompson to come through with a mediocre game to clinch the upset.

Instead, he dropped one of the worst games of his storied career.

Klay missed nine of thirteen shots, including all four of his three pointers, and barely added any other counting stats—his total of 11 fantasy points marked a devastating and untimely low, and clinched my eventual 901 - 894 loss.

I was apoplectic. In the impotent nerd rage only caused by fantasy losses, I pulled every single game of Klay’s career and built out a simulation of a million fictional games. I had to see exactly how badly we botched this, and, in the alternate Mike universes, which ones ended up with the victory.

Here is that simulation. The peak is the most commonly occurring score, with the height corresponding to the percent of games that produced that point total.

In my timeline, Klay had 11 points. He outscored that total in 96.6% of these fake games, with an 85% chance he’d get 18 and at least tie the game for me.

I’m still bitter in 100% of my real life.

Kickers, the cruelest of all

Friend of the program Joe sent in a story on behalf of the guy he beat, a truly elite flex.

Joe, who seemed to commit the cardinal sign of playing a New York Jets player in a meaningful fantasy football game, managed to overcome many decades of Gang Green incompetence to spring an upset on his poor opponent. The vehicle for this pain?

Nick Folk, the Jets’ kicker.

Folk played for the Jets for seven seasons, peaking with this game-winning field goal against the Colts in the playoffs. He averaged 7.4 fantasy points a game for his career, and found surprisingly consistent employment as Joe’s fantasy kicker.

No one ever finds joy in a fantasy football loss, but no defeat stings worse than a shocking upset on Monday nights. For Joe’s poor opponent, he woke up Tuesday to a nineteen point, five field goal night from Saint Nick.

Here’s how every Folk game turned out, and where the one Monday in hell for Joe’s opponent landed.

More evidence for the movement to ban kickers forever.

Months of work lost to a rounding error

Reader David chimed in with this story, lightly edited below.

He managed a team in the most brutally competitive version of fantasy basketball, a thirty team league with strict salary cap restrictions on its players. In these category leagues, your team must be capable of production across a variety of stats, scoring but also maintaining efficiency and counting stats outside of points.

These leagues rely on managerial ingenuity and guile, but also on luck; David’s ran out right at the the start of the playoffs, with his first two picks injured and ruled out.

He cobbled together a makeshift team and clawed his way into the final day of games, where he lost by a 0.02% margin on the free throw line and two total points scored. This margin? Easily solved by one foul call on any of his players.

A rare instance of rooting for the referees.

Injury apocalypse

Another friend of the site, @HiddenUpside, shared his own category-based misery. After a season dominating with three superstar guards in Trae Young, Damian Lillard, and Devonte’ Graham, he’d secured top seed entering into the playoffs.

All three of these foundational pieces ended up injured and/or missing time, and he quickly fell to the eighth seed. Upsets and injuries ravage fantasy squads often, but rarely to that extent. Young, Lillard, and Graham produced 18.9 win shares this season, per Basketball Reference.

In terms of on-court production, that sum represents the 2019-20 Lakers losing LeBron James and Anthony Davis right before a series against the moribund eight seed.

Self-inflicted wounds sting the most

Sometimes, the blame for a loss starts and ends with the player in charge. Reader Eric shared his own moment of self-sabotage.

Two years ago I lost a league by one steal because I messed up my streaming and dropped someone who had an extra game. They got a steal in the extra game and a guy three-peated my league. We cancelled it the next year because no one was active any more. I made the championship three times and lost 5-4 each time.

Eric’s player in question was Marvin Bagley III, who did get a steal in that mistaken lost game.

Losing in the finals once might make you question your faith and God. Losing three consecutive times, once by a lineup mistake, and indirectly causing a league to fold? You’re either cursed forever, or the Buffalo Bills.

A surprising hero comes along

History may remember the winners, but fantasy addicts will never forget the role players who morphed Super Saiyan-style into unbeatable statistical demigods at the exact wrong moments. I once made the finals of an odd fantasy football league in part by Sammie Stroughter, the return man for the 2009 Tampa Bay Bucs and producer of special teams points.

These midseason transformations haunt twice as much when you’re on the losing end of them. I heard from @Kanowins512, who fought the supersized version of JaVale McGee in another intense salary dynasty league.

McGee, a journeyman big known for his athleticism and public beef with Shaquille O’Neal, turned into a dream killer in March of 2019. Kano’s opponent picked McGee up on a whim before their two week matchup, and this one small choice in a season full of similar decisions ended up deciding the finale.

Per game, McGee doubled his career points and rebounds totals in this month, all while shooting over 67% from the field.

A career stretch for the bench player earned McGee a second contract with the Lakers, and cost Kano $200. The guy who once dunked on two rims managed to dunk on real and fantasy teams.

Haunted by a Madden cover

Finally, we end with a powerful story from another friend of the program, Steve, who signed up for the Peyton Hillis roller coaster without any safety harnesses.

Year: 2008

Stakes: Round 1 of the 2008 Weasel Bowl Playoffs

Belligerents: Steve and Dylan

Outcome: 135-125 Dylan victory

To understand what made this so painful, you must first understand The Streak. Our fantasy football league was founded in 2003, with the founding principle being my confidence that I could whoop all my friends' asses at it because I knew more about football than they did. And I wasn't wrong! We were young, and mostly stupid, but I was slightly less stupid enough to make the playoffs in every season from 2003-2008, with the exception of 2006. Yet, no matter what I did, I always met a grisly end in the first round of the playoffs. And to add insult to injury, I would also lose the subsequent placement game that the computer puts on your schedule so you have something to do in the week after you get eliminated from the playoffs. And so you understand, a great deal of my self worth is tied up in being able to beat my friends at fake sports, and my winless postseason streak had become a source of great ridicule. So after making the playoffs in four out of five seasons and coming up 0-8 in the postseason, you must know that I was a man on a mission. 

I kicked off the season by trading Sammy for the first overall pick. Sammy picked number 1, and he didn't want it. I picked 6th and I was sick of losing when it mattered. I traded Sammy my my 1st and 2nd for his 1st and 2nd. So, all of you sucker MCs who think RJ and I just started getting discounts from Sam this year, think again. I drafted LaDainian Tomlinson, Sam drafted Tom Brady (who tore subsequently tore his ACL but a few weeks into the season). I went a workmanlike 7-5-1 despite splitting the points title with RJ (who it bears mentioning went an extremely odd 7-4-2). The playoffs begin, and I face one of my most detested rivals: Dylan. Of course, this is the playoffs and things go just how you'd expect. Dylan gets out to a 135-108 lead, and all I have remaining is lowly Peyton Hillis, who has taken over the Broncos backfield after injuries to Tatum Bell and Michael Pittman (I think; I might have the order wrong). But I needed Mr. Hillis. I was missing Clinton Portis, and for some reason my quarterbacks were Shaun Hill and Matt Schaub. But despite the 27 point hole, Peyton Hillis comes out of the gates with 17 points in the first quarter (thanks in part to a very strange scoring system that we actually haven't changed that much). This tilts the scales so much that now it seems as though it's a foregone conclusion that the husky Razorback will vault me past Dylan and into the semifinals for the first time in my burgeoning fantasy sports carer. 

The very next possession, Peyton Hillis, perhaps on the high that comes with the knowledge that you're changing the course of bragging rights in suburban New Jersey, felt it was time for a heat check. He decided to reach for the stars and hurdle a guy. He immediately gets thumped and, as RJ said, you just knew he was done. He exited the game, the playoff winless streak went to 0-10, and I was left with no light at the end of the tunnel. 

Somewhere, Steve has a collection of broken Madden 2012 discs, their covers burnt to a crisp.

If you have a great fantasy story and want to share, email me at [email protected]. I’d love to hear from you.

Hope you and yours are healthy and doing well!