Matt Dougherty

The Commissioner of 300 Fantasy Leagues

The Commissioner of 300 Fantasy Leagues by Utter-Fantasy Writer & Illustrator Doug Bowles

As a fantasy football fanatic, as a fantasy commissioner and as the creator of, I couldn’t help but take notice of someone in our fantasy football community who is the commissioner of over 300 leagues. His name is Matt Dougherty, and he is the owner of and Since 2007, Quest has been the top provider of long-term fantasy football leagues, who’s specialty is dynasty leagues, but who also hosts keeper leagues and the traditional (or “redraft”) leagues.

My mission, and Matt has accepted, is to find out a little about Mr. Dougherty, and information regarding his fascinating fantasy football websites. I hope you enjoy our conversation!

Utter-Fantasy Question #1 to Matt Dougherty) My first introduction to fantasy football was back in 1985, so I have been doing this for a while. I have an educated guess that you have been doing this for a while as well. What got you interested in fantasy football to begin with?

I have been a huge NFL fan and diehard Washington fan and season ticket holder since I was a child. HTTR!
I discovered fantasy sports in the 90’s and started with a redraft league, then keeper leagues and once I discovered dynasty, I was hooked. I love the bond that is formed with your team and fellow league mates as well as the rivalries that form. Dynasty leagues are year-round and I love the ability to trade and interact with league members during the off-season.


Utter-Fantasy Question #2) That first league that I started with back in 1985, is still a fun and competitive league today. How many fantasy football leagues do you participate in? Are there 1 or 2 that you have participated in for a number of years?

With the growing number of leagues I am running, I have had to cut back the number of leagues that I am in, but I still participate in about 15 dynasty leagues. A couple of them began back in the early 2000’s.  I have also recently discovered Best Ball dynasty leagues, which are leagues where there are no waivers and the system selects your best lineup each week based on the highest scoring players.  This format is great for owners with multiple leagues and limited time. We just started offering this league type at QuestFFL with great success.


Utter-Fantasy Question #3) I am the commissioner of a couple of leagues myself, and that’s plenty. How does any human being manage to be the commissioner of over 300 dynasty leagues?

It takes a good deal of planning and being as organized as possible.


Utter-Fantasy Question #4) What is the most demanding part of being the commissioner of so many leagues?

Definitely the time commitment.  In May, Quest and FFLS held its annual Rookie drafts. Over 2 weekends I ran close to 300 rookie drafts. I don’t think I left my computer or slept for a week straight. I had a blast following all of the drafts though and interacting with all of the owners!


Utter-Fantasy Question #5) You are the owner of and What was your inspiration for the 2 sites?

I used to participate in several leagues where the commissioner was unresponsive, took days to process trades and was not receptive to changes in the league.  As a commissioner I take pride in being very responsive. I have my smartphone tied to my hip and always respond to questions and trades very quickly. I also welcome constructive comments and criticisms on ways to improve the sites. These are your leagues!


Utter-Fantasy Question #6) Is there a difference between Quest and FFLS?

The FantasyFootballLeagueSite has an extra flex spot for lineups and also uses a taxi squad which is modeled after the NFL practice squad.  At QuestFFL we offer a wider variety of dynasty and keeper league types such as Best Ball, SuperFlex, Devy and Auction Salary Cap Dynasty leagues as well as a traditional keeper leagues where you keep a total of 7 players each year.  We also run a Quest League of Champions- invite only league, reserved for our most active owners.  This a free league with a large 1st place prize.


Utter-Fantasy Question #7) Can fantasy football owners join QuestFFL and FantasyFootballLeagueSite even after the NFL season begins?

We stop offering startup leagues right before the start of the season but there are usually some orphan teams that are available at big discounts during the season.


Utter-Fantasy Question #8) What’s the most common question that you are asked about your two fantasy football websites?

Will my league ever fold and will I get paid my winnings at the end of the season?

With the demise of several large dynasty sites in recent years, we wanted to provide more security for owners.  We just recently moved all league funds to LeagueSafe at QuestFFL and FantasyFootballLeagueSite.  All league funds are held in a LeagueSafe escrow account.  The commissioner has no access to these league funds.  At the end of the season, a majority of league members must vote to approve the allocation of winnings.  Winnings are sent by the end of December each year.

Since offering dynasty leagues in 2007, we have never folded a traditional dynasty league. While most of our owners are committed long-term, each year some owners decide to leave the league for a variety of reasons.  In order to entice new owners to take over the orphan teams, we offer these orphans at significant discounts. We currently are offering orphans at close to 40% off the regular entry fee. The payout structure remains the same even if a team gets sold at a discount.


Utter-Fantasy Question #9) What tends to be the most popular league that fantasy football owners join at Quest and FFLS?

Besides our traditional dynasty league, Devy dynasty leagues are becoming increasingly popular. In this league format, there is an annual draft in August reserved for non professional players. Any college player is eligible.
This allows you to follow college players as they make their way to the NFL. You can even select a high school player.  In the first devy draft I ran many years ago, an owner selected Dorial Green- Beckham who was a high school senior at the time.


Utter-Fantasy Question #10) On Twitter you write- “Send me your #dynasty questions!” Is fantasy football advice something the 2 sites provide, or something you do for your twitter followers?

As a commissioner, I need to be impartial and do not offer any advice to owners on either site.  However, I do offer advice on my personal Twitter account, @MattDynastyFF.  I have run over 300 drafts and processed thousands of trades so far this offseason so I have a great idea of player values.


Utter-Fantasy Question #11) Where would you like to see Quest and FFLS, 5 years from now?

The possibilities are endless.  I always welcome and encourage feedback from owners on ways I can improve the leagues. In recent years I have implemented many changes including implementing a toilet bowl, 3rd place game, additional roster and flex spots.  All of these changes are based on feedback from owners and will continue to make improvements based on the feedback I receive.


Utter-Fantasy Question #12) Is there anything else, that would you like fantasy football owners to know about Quest and FFLS?

On both sites we have a large number of startup leagues currently open and will have drafts running continuously through the start of the season. We also have several dynasty orphan teams that are discounted up to 40% off the normal entry fee.  We also offer an additional $15 discount off any purchase for new owners.

Looking forward to great 2016 NFL season!



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