How to Make Your Fantasy League Memorable and Enjoyable

This is a guest post by Christopher Connolly, a close friend and an early supporter of WePay.  Chris has more than 10 years experience as a commissioner of over 30 fantasy leagues, and has some pretty valuable lessons to share. Learn more about how WePay can help you collect money for your fantasy football league.

After reading raberman’s post on How to Plan a Great Fantasy Football League, I thought there were a few areas where I could elaborate and a few things I could add.

First and foremost, fantasy sports is a game, and a means by which old friends can keep in touch, even over vast distances.  I’ve retained some of my best friends from high school, going on 10 years post-graduation, thanks to our shared fantasy sports leagues.  Some of my most valuable friendships were fostered and carried on via fantasy sports.  As commissioner – you have the power to make a league so enjoyable that it can carry on for years and survive numerous life changes on the parts of your co-managers.  Take every opportunity to embrace your role and foster a fun, competitive environment for everyone involved.

My fantasy sports career kicked off slowly over a decade ago.  A busy high school student at the time, I didn’t know what this “Fantasy Baseball” even was when my friends recruited me into a startup league.  It didn’t take long to catch the bug.  I caught it so severely, in fact, that I would soon take the commissioner reigns of our annual baseball and football leagues and never look back.

Because I was a pretty terrible player in my formative fantasy years (some would argue that nothing has changed), I realized my true calling was as commissioner, making each season a memorable one for all participants.  I quickly realized that the commissioner can single-handedly make or break a fantasy season.  While I’ve dealt with my fair share of controversies – from managers hacking each other’s accounts and dropping entire teams to collusion, for the most part I consider my career a success.

Over the years, I’ve come up with a few principles I feel are essential to making your league successful, memorable, and most importantly, enjoyable, and have been asked to share those with you.

It’s all about the draft

There is little doubt amounts fantasy diehards that draft day is the best/most important day of the year.  These diehards are right.  Pre-draft, every manager is so full of promise and excitement, and its your duty as commissioner to embrace this excitement.  Luckily, that’s not too hard.

It’s not always possible, but I highly recommend hosting a live, in-person draft.  I’ve done my share of online drafts, and they will never compare to the excitement and camaraderie fostered when 10+ people congregate to draft for a fresh fantasy season.  Start early- I try to set a date for our draft three months before the season starts.  Whether your league mates are juggling school, work, or a family- planning ahead is the only way you’ll find a date that works for everyone in the league.

If you are lucky enough to have a live draft- congratulations.  Now there’s plenty you can do to boost your credibility as a commissioner.  Be prepared- poster board or a pre-made draft board are key to keep the draft organized and moving quickly.  Slow drafts are the bane of any league’s draft, and it’s your responsibility to keep things moving.  Every league has their slow drafters- but solid police work should keep that in check.  Throw in some food and beverages, and you’re well on your way to a great season.

Draft day is my single favorite day of the year- to me, there’s nothing better than 10 guys crowded in someone’s living room, fumbling with draft research while shouting out names for 4+ hours.  Basically, try to make it like the scene in Knocked Up before Debbie busts in on Pete’s draft.  A little planning goes a long way.

Be Invisible

Now that the league is drafted and the season is underway, the hard work is just beginning.  It’s easy to get caught up in the power wielded by a commish (who knew that approving trades in a fake league could feel so empowering) but you must resist the temptation to be heavy-handed and aggressive.  Remember, you are but one member in the league.  Other than approving trades and keeping an eye out for suspicious behavior, you are on equal footing to every other manager.  Blend in, be inconspicuous, and let the league develop on its own.  Manage personalities when you have to, but otherwise, you’re there to make sure everyone has a good time – not to be their nanny.

Be Consistent & Committed

There’s nothing worse than a commish who has double standards.  If you have the power to approve trades, do it consistently.  Don’t approve your own trades immediately, and then wait three days to approve your opponent’s.  You have to hold yourself to a higher standard than the rest of the league, particularly if there is money involved.

Accepting the role of commissioner brings with it tremendous responsibility.  You alone are in charge of approving trades and keeping an eye on the rest of the league.  Be vigilant in preventing collusion and prevent managers from giving up.  It may take anywhere from a few minutes to an hour a day, but you must devote considerable time to taking care of your baby.  Respond to emails and league messages.  Let people know what you think of their trades.  Foster conversations to keep the message board lively and get all the managers involved.  Like a plant, your league needs food & water to survive.  Don’t let it wither and die.  What an awful metaphor, but it’s fitting.

Incentivize

It’s important to keep all your managers involved throughout the season.  By the time midseason rolls along, many of the teams in your league could already be eliminated from contention.  You need to prevent them from giving up and tipping the balance of power even further in the leaders’ favor.

I’ve found two successful ways to accomplish this.  The best way is to implement a booby prize of some sort.  In my leagues, the last place team has to buy the food and drinks at the following year’s draft.  So far, it’s worked wonders in keeping the last place teams involved.  In fact, the most exciting part of the last few weeks of the season is watching teams try harder than ever to stay out of last place.  We’ve had photo finishes for last place, infinitely more exciting than the runaway victory by our first place manager.

And while this is obviously more common, there needs to be an incentive to finish in the top few places.  Prizes don’t have to be monetary- in the early years of my leagues, the pride earned from winning trumped any money we could have won.  However, there will come a time when even pride won’t cut it anymore.  Managing a successful fantasy team takes an inordinate amount of time, and channeling my inner economist, there’s a time value we have to associate here.  Find a way to reward your managers for sacrificing their lives and jobs for the good of your league.  But keep it reasonable – this is only a game, nobody should ever be stressed out about the outcome of a fake game built around a sport.

Mind your Finances

If you do decide on a monetary prize, I’ve learned some valuable lessons over the years.  First, collect the money up front.  It makes everything much neater as the season progresses, because if you don’t have everyone pay by draft-day, you’ll inevitably forget who has paid and who hasn’t, and you’ll have a mess on your hands.  Plus, the “pain” your other managers feel by dishing out the money ahead of time is the most effective motivator you have, this will get them playing with more intensity, your ultimate goal.

The best way to encourage your fellow managers to pay up is to punish them for failing to do so.  A lot of online leagues give the commissioner power to block managers from posting messages or changing their team name.  These are quick and easy ways to inflict a little pain on a deadbeat manager.  If this fails, don’t hesitate to shame the manager publicly for not paying.  Never underestimate this power.

This final point I can’t stress enough:  Being commissioner does not entitle you to run a ponzi scheme.  The entry fees you collect are not an interest free loan.  I’ve fallen into this trap.  Sitting on $1,000 in league entry fees, post-draft at a casino (admittedly, it was my fault for putting myself & the league in that situation), resist the urge to bet the league’s money on a craps table.  And if you get lucky and double the league’s pot, put it in the bank immediately.  I went through a few-year stretch where I paid the price for spending the league’s entry fees, figuring I’d be good for it when the season ended and we had a winner.  Inevitably, I let fantasy seasons run into one another – paying the winner of our baseball league with the entry fees collected from football and vice versa.  Don’t be a fantasy Madoff.  You see where it got him – it’ll do the same to you.  Keep the money separate and secure, and you’ll be much better off.