Commish HQ: So You’re Going to Start a Fantasy League. What Now?

By Reginald James
Reginald James

You’ve decided that you’re finally going to start your own fantasy football league. Maybe you’ve been corralled into running the office league because you just couldn’t say “no.” Whatever the reason, you’ve found yourself in the position of running a league for the first time.

No worries. Welcome to CommishHQ!

Folks are often surprised to find there’s more involved to running a league than they thought. Some soon learn it’s not as fun as they thought it might be. There are many stories out there from frustrated commissioners who will tell you it’s a thankless job. There are other fantasy commissioners who will tell you that it is fun. They’ll tell you they are not pulling their hair out trying to collect league fees.

Which type of commissioner will you be?

That’s what CommissionerHQ and Ask the Commish series is all about. Our goal is to have you keep the hair on your head intact, and for you to have a fun and perhaps even rewarding experience running a league.

We’re going to discuss three areas that a first-time fantasy commissioner should address, that will provide a good base from which to start. If you put in the time now really thinking about what kind of league you want, you are less likely to end up crying about how much it sucks to be a fantasy commissioner on Twitter.

For the Love of Fun or Money?

Will your league play for money, or will it be just for fun? It may seem like everyone else is playing for money but that doesn’t mean that your league has to do it.

First, consider the makeup of your league. Will this be a “family and friends” league? Is this an office league? What’s the mix of new versus experienced players? Now take into account that you’re running a league for the first time.

I’m a big fan of keeping things simple. If you start out playing just for fun, the stakes won’t be that high for you if you suffer any missteps, and you just might. The new folks can learn the game. You can discover what it’s really like to run a league without adding the element of money into the mix. People start to act differently whenever money is involved, and not necessarily in the best ways.

Hopefully, your goal is to have the league last for a long time. Just know that the league members your start with may not be the same ones you’re playing with five years down the road. You’ll realize soon enough that some of your family or friends aren’t the best people to be in a league with. If someone is acting up when you’re not playing for money, just imagine what will happen when you are.

You’re going to want to give your league a chance to find a good core group of players who certainly may care about winning (and winning money) but not at the expense of busting the league up over a cheating scandal or ill-behavior. Hopefully, protecting the league and having fun with the other league members will become just as important to them.

If you do decide to go the money league route the first year, decide what kind of payout you’re going to have. Are you going to have pay tiers or have a winner-takes-all format?

The downside of having a sole cash winner pops up when some people realize they’re no longer in contention to win. They may lose interest and devote less attention to managing their team. When these types of players start to pout, it can have a negative affect on the overall competitiveness of your league.

“Money slots” of first, second and third place still gives players a chance to win money. Even though they might not have a shot at winning the league, they’re more likely to stay interested and compete the duration of the season.

The Rules are the Rules

Yup. It’s that simple.

First and foremost, if you are not willing to enforce the league rules, stop reading this and resign as commissioner, right now. You set the bar for what the league expectations should be - year one. Do not waver from the rules you establish.

Do not let your personal affiliation with anyone deter you from doing your job as a commissioner. This means no allowances or favors for anyone - not even for grandma. The slope can get real slippery once you make that one small exception to a particular rule for one person - especially if others find out.

Learn to be consistent in this regard and everyone else will follow your lead.

Secondly, read the rules of whatever platform you’re using. Are there any established rules that you want to modify? Are there are any additional rules you want to add that the existing rules don’t cover? Put all changes or additions in writing.

Next, you’re going to play the role of devil’s advocate. There will always be a player who is going to look for the loopholes in the rules to exploit. You’re going to beat them to the punch. Craft rules to address any such issues. Again, put it all in writing, be as specific as you can. You might consider giving examples to help illustrate a particular rule that you’ve come up with.

Will you miss something? Maybe. However, if you start out with the mindset that you’re going to enforce the rules and make them as loophole-proof as possible, you’ll go a long way in avoiding hearing someone smugly say, “Well the rules don’t say I can’t do it.” You can live without that nonsense.

Clear Channels of Communication

As a league commissioner, be transparent in everything that you do. You are no longer one of the crew. You now have two hats to wear. When you are wearing your commissioner’s cap, you have to do what you can to be above reproach. Someone may still falsely accuse you of wrongdoing. However, if you establish a track record of open communications from the very beginning, with the members of your league, false accusations should have little affect.

Communicate all official moves you make as commissioner. Make sure that the league knows ahead of time about any official moves or decisions you’re planning. Do not get in the habit of last-minute announcements.

All league correspondence should be cc’ed. This protects you from claims that someone didn’t get your email. I start off every league letter with:

The following has been sent to all league members:

What about texting? Text if you like. I find that’s it’s easier to archive email messages, especially if you’re in the habit of backing up your computer. Whichever option you choose always include yourself as a recipient. Additionally, make sure that you can easily retrieve any past correspondence. You might need to pull up something as evidence.

If you find yourself trying to mediate a dispute via email, make sure you cc the parties involved. Do not have private conversations with either party about the issue. This protects you from accusations of favoritism.

No matter what you’ve heard, being the commissioner of a fantasy league doesn’t have to be an awful experience. The fact that you’re reading this means the stories haven’t deterred you from at least giving it a shot. That’s great. Try your best to plan ahead, keeping the big picture in mind. Make sure that the league rules have clarity and are as iron-clad as possible. Your expectations and actions as a commissioner should be clear - transparency is the key.

Let me know how it goes. I’d love to hear your stories. Your questions may be featured in upcoming installments of Ask the Commish! Hit me up, The Commish, at