Welcome back to the series where we learn things the hard way so you don’t have to.  This time around I’m going to write about something that we are all very familiar with.  Many times in a negative way.  Prompt payment is a must for any fantasy football league.  And here is why.

I’ve commished fantasy football leagues since the mid 90’s.  Since 1996 to be exact.  In the beginning it started out as a league with friends.  As such I wasn’t nearly as diligent at collecting league dues as I am today.  After all these guys are my friends.  If I don’t get payment in time I’ll just go to their house and bump some heads.  I suspect most of us started fantasy football in a similar way.  It’s a game and was treated as such when we were younger, dumber, and just cared less.

As time went on the inevitable turnover that comes with a long-running fantasy league began to rear its ugly head.  As new people come on the friendship factor becomes more and more vague.  Either that or people move away, get married, have kids and life takes its twists and turns for all of us.  Either way the result is the same.  Prompt payment of league dues becomes harder and harder to achieve every single year.

And here’s where the hard knocks takes place.  A couple years ago I didn’t receive league dues from one of my owners.  At all.  That means I as commissioner had to fund that spot and cover the extra payout amount that year.  I felt it was my responsibility since I hadn’t done my due diligence and demanded payment up front.  It all ended up ok for me because the owner paid double dues the following year but it doesn’t always work out so well.  I’ve heard of leagues disbanding, people taking money and running, someone drafting a team and then quitting, and various other sordid tales.  I’m sure many of you have similar stories and not a one of them good.

Of course as my obsession with fantasy football grew I needed to branch out to the online community as well.  My friends weren’t all into dynasty.  Not necessarily into the hardcore leagues and so I found my way into leagues with people I don’t even know.  The same logic applies here but it applies ten-fold.  Giving someone you don’t know money and expecting it in return is a big deal.  Similarly demanding payment and expecting said payment from total strangers can be a practice in frustration.

So with that in mind this lesson isn’t just applicable for owners getting their league dues in on time.  It is also for commissioners paying out winnings as promptly as possible.  I’ve been in and seen too many situations where payouts didn’t occur within a reasonable time period.  Sometimes they don’t occur at all.  So what do you do?

Well, the lesson here is no matter who you’re playing with or for how long you’ve played demand payment up front.  Nothing starts until all league dues are collected.  No redraft draft, startup dynasty draft, rookie draft, or offseason waivers happen until the money is collected for the following year.  It sounds as basic as can be but it’s amazing how many times this gets overlooked because we’re too excited to get things rolling.  Even if you’re playing with close friends it’s better to be safe than sorry.

Also, either have an extremely reputable commish (either recommended by someone you know or an actual trustworthy friend) or use leaguesafe.com.  This ensures not only that dues are paid on time but that winnings get paid out automatically at the end of the season.  It sends the annoying payment reminders to individual owners so that you don’t have to.  Even making them pay a late fee if they don’t pay in time.

So what are your experiences with prompt payment?  Have you had good luck or bad?  I know some of you have horror stories to share.  Hopefully whether you’re new to fantasy football or have been doing it forever this lesson rings true for you.  Maybe for some of you it’ll prevent you from learning the same lesson that I did.  The hard way.