Guide To Running A Decent Fantasy Football League

How to keep things fun and challenging without alienating your friends, family, co-workers and yourself.


I t brings me absolutely no pleasure to say I run two fantasy football leagues and it brings me somehow even less pleasure to say I’ve run one of those leagues for six years and the other for seven. LIFE COMES AT YOU FAST.

That being said, if one good thing has come from volunteering to run these two leagues, it has been learning how craft a really good game, like, understanding how to keep a game interesting but accessible, how to cultivate parity but try to reward strong analysis and how to motivate people to compete throughout the entire span of the game.

If you start a standard fantasy football league and basically, as league manager (also known as “commissioner”), exert the least amount of energy possible while running the league on auto-pilot, you’ll invariably encounter the following things amongst — it’s humorous to keep this in mind — your friends, family and co-workers:

  1. People will fail to pay their entry fees.
  2. People will try to cheat, mainly via colluding with others.
  3. People will argue with each other and complain to you.
  4. People will threaten to quit if X doesn’t happen.
  5. People will lose interest and give up, causing a competitive imbalance.

Sound fun? This is why, even if you really didn’t and don’t want to, you’ll ultimately end up having to become a more active league manager if you want to maintain a long-running league.

Inspired by Samer Kalaf’s Deadspin post yesterday “How To Run A Fantasy Football League Without Making Everyone Hate You”, I’ve decided to list out some of my own general and specific pieces of advice for crafting and running a decent fantasy football league.

Make the roster settings fun without making them too difficult for a newcomer to understand.

If you have 10 or 12 or even 16 friends (including yourself) who are all super fluent in fantasy football game mechanics and who are all super devoted to competing in your league, then fine, go crazy with your roster settings.

But the general notion is that whether it’s in year one or year three, you’ll eventually find yourself needing to replace some members of your league (either via you kicking them out or them quitting).

In making changes to the roster settings*, the general rule of thumb is to ask yourself whether or not this change to the standard roster settings that everyone playing fantasy football knows would be reasonably accessible and comprehendible to any newcomers. After all, nobody wants to pay money to join a league feeling like they’re at a competitive disadvantage.

The more trading the better.

Trades are one of the most universally beloved things about following real-life sports so it makes sense that trades in fantasy sports generate equivalent amounts of excitement and frustration and fun watercooler analysis.

As league manager, you have the responsibility to stoke as much trade conversation as possible amongst your league’s teams because trading occupies the same thrilling and excruciating plane as gambling and gambling cultivates peaks of excitement and providing peaks of excitement should be the goal of any fantasy league.

Keeper leagues, especially ones that let you trade draft picks*, tend to stoke greater amounts of trading. The most common type of a trade — in real life and in fantasy — is often between a team near the top of the standings trying to improve their odds of winning the current season’s championship AND a team near the bottom of the standings trying to improve their chances of having a winning team for next year or sometime in the future.

Speaking of trades, the league manager should be the one to approve/veto all trades.

Some leagues let other teams vote on a trade before the trade is made official. This is fine and I suppose it embodies the democratic spirit of this country (NOT REALLY) but it also leaves the trade participants vulnerable to delays caused by other league members neglecting to vote on the trade or maliciously refusing to vote on a trade, consequently causing the trade participants to occupy a longer-than-desired stasis in which they can’t make roster moves until the trade is made official.

To avoid this, the league manager should inhabit the responsibility of approving and vetoing trades. As league manager, even if you have a team in the league (which is almost always the case), you have an over-arching responsibility to preserve and perpetuate the league’s healthy existence.

When it comes to trades, the healthiest leagues are able to discern the difference between bad trades and collusive trades. Bad trades are fine. If a team is dumb, a team should be allowed to be dumb. Collusive trades are toxic. They create a nearly unshakeable toxicity to the league proceedings and are probably the #2 cause (behind apathy) for why people quit leagues.

The problem with putting trades up to a league-wide vote is that league members — especially when some don’t directly know each other IRL — tend to be bad at discerning the difference between bad trades and collusive ones. On the other hand, the league manager should have the best vantage point as far as knowing the relationships amongst league members and therefore, the league manager can be the definitive voice in adjudicating on trades that could be either collusive or just bad. General rule of thumb: Let everyone hate you rather than everyone hate each other.

Create incentives to keep people interested throughout as much of the season as possible.

The worst part of any fantasy football season is when teams — almost always teams near the bottom of the standings — start giving up. This ultimately creates a competitive disadvantage in which teams competing to win, can sometimes win money or lose out on winning money based on whether or not the teams they are playing and the teams their nearest competitors are playing have already given up and are failing to field competitive rosters.

To prevent this from happening, I recommend the following:

Create a midseason side tournament.

Right now, people in my league pay $125 for their entry fee. $100 of the $125 go to the regular season prize pool (payouts: 1st = $500, 2nd = $300, 3rd = $200). $25 of the $125 goes to a side tournament prize pool (payout: $250 for the side tournament winner).

The side tournament’s function is to give teams an opportunity to win money even when their chances of winning regular season prizes seem bleak.

It can really take any form so long as you keep it separate from the regular season’s proceedings. The way my leagues’ side tournaments work*:

  • Starting in Week 13, I split the league into two groups of five. For Week 13 and Week 14, the teams in these two groups try to score as many points as possible over the course of the two weeks (a little bit like World Cup group stages).
  • At the end of Week 14, the top two teams from each group enter the Week 15 elimination rounds.
  • In Week 15, the top team from Group 1 faces the second team from Group 2 and the top team from Group 2 faces the second team from Group 1.
  • The winners in Week 15 move onto an elimination match in Week 16 and the winner takes home $250.*

You don’t necessarily need to copy this format. Just having something that doesn’t disturb the integrity of the regular season competition yet gives hope to teams on the verge of giving up will make your league more competitive throughout.

Make how well a team finishes determine how good of a draft pick they get the following year.

On top of the side tournaments, I further incentivize teams to stay interested and competitive for as long as possible by making how well they finish in the standings dictate how good of a draft position they have in the following year’s draft (this excludes 1st, 2nd and 3rd place which already have the incentive of winning prizes). Thus the way the draft order for the following year’s draft looks like this:

  • 4th place receives the 1st pick in the following year’s draft.
  • 5th place receives the 2nd pick in the following year’s draft.
  • 6th place receives the 3rd pick in the following year’s draft.
  • 7th place receives the 4th pick in the following year’s draft.
  • 8th place receives the 5th pick in the following year’s draft.
  • 9th place receives the 6th pick in the following year’s draft.
  • 10th place receives the 7th pick in the following year’s draft.
  • 3rd place receives the 8th pick in the following year’s draft.
  • 2nd place receives the 9th pick in the following year’s draft.
  • 1st place receives the 10th pick in the following year’s draft.

Invariably, once people realize how big the difference between the 1st pick and the 7th pick in the following year’s draft, they’ll continue to compete even if they’ve been eliminated from winning any prizes in the current season.


Regardless of how you proceed with managing the technical aspects of the league, remember, probably the biggest success you could ever achieve as a league manager is making sure everybody realizes fantasy football is just a game (even more “just a game” than the sport itself). The goal is to have lighthearted fun.

This unfortunately is easier said than done, especially with the ever-toxic aggression-cocktail of money and pride involved. This guy learned the hard way:

From a prognostication perspective, football is a violently volatile game. Seventeen weeks is a near meaningless sample size for the average person to analyze for actionable patterns. Great players have bad games out nowhere, bad players have great games out of nowhere, turnovers hinge on the capricious prolate spheroid shape of the ball and just in case you haven’t heard, players get injured ALL THE TIME.

Meaning, outcomes in football and consequently fantasy football hinge hugely on luck and accident. The last thing you want is you and your friends and your family and your co-workers’ emotional well-beings predicated on the outcomes of such unpredictable cruelty.

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