Beginners Guide to Starting a New Dynasty League

How should I go about starting a keeper or dynasty league?  This is one of the most frequently asked questions to fantasy analysts in the offseason.  There’s no one right answer, and I’ll be honest – I’ve never been enough of a martyr to run one myself.  Lucky for me, I’m part of some really well run keeper and dynasty leagues and I’ve never had to worry about anything but my own team. 

I have some insights into some things you need to consider, though, since I’ve played in quite a few keeper and dynasty leagues the last few years.  I’ve also had some downright awesome commissioners that run their leagues better than Bud Selig ever ran the real one.  This piece is going to give you some important ideas and questions to consider before bringing a new keeper or dynasty league into the fray.

General Advice and Admin

Good People

This is the absolute most important thing when creating a long-term league.  You need to create a core of owners that are dedicated and are willing to put in the time and effort into owning a fantasy team for the long haul.  The last thing you want to do is replace half the owners every year, or worse – fold the league 2 or 3 years in.

It’s nice when everyone knows each other and if they’re friends, but it’s more important that you have good people.  Pass over your flaky friend that can’t even bother to set his fantasy football lineups.  Invite your work acquaintance that you talk shop with after the marketing meetings instead.

We live in a golden age of communication as well.  You can go onto various websites and find a league to join or find people to join your own league.  I found several leagues through Fangraphs last year and believe this kind of thing is common on several fantasy sites.  Even if you don’t have enough friends cool enough to commit to a keeper or dynasty league, you can find good owners out there on the web.  Heck, I’ll try to join one or two this season if you ask me early enough.

Rules and format

It’s usually best to start simple before making too many custom tweaks.  Play a season or two of roto, categories, or points with minimal changes to the standard scoring.  As you become more experienced, make some tweaks to suit your desires.

I can tell you from painful experience that if you get too customized too quickly you’ll miss something, and that something might make the entire first season no fun.  Just to give you an example: the first points league I ever played in had daily waiver moves with no start or pickup limits.  The eventual champ literally didn’t play a catcher and instead favored streaming an extra 6-7 pitchers per week.

It was an absolute garbage situation, and the commissioner didn’t change it until the next season since those were the agreed upon rules.  Luckily for the commissioner, he had good people as recommended above, and we all took the lumps of that brutal first year. It has now blossomed into a highly competitive league with a lucrative championship pot.

Hopefully you can get a free learning moment here from our mistake.  If you are making the move from roto or categories to points for the first time, just do a weekly league to start.  If you absolutely demand daily waiver moves then you need to implement a starts limit or someone will abuse the system in the same way my league mate did.

Write a brief constitution

Talk to your league mates and discuss what you want the league to look like.  Vote on the particulars.   After that, take an hour or so to type up an official League Constitution.  This way, the bylaws are completely transparent.  There can be no accusations of favoritism or unfair judgment decisions. Everything will be in writing.

One good idea is to do it in a google doc and have the link to the constitution right on the league’s homepage.  This way, if a player needs 100 games to be kept – it’s clear right from the beginning and the owner can find out for himself without you having to give him the bad news. This will make rulings more formal and seem less subjective and personal, which is definitely helpful for a commissioner.

If you do auction, have a calculator/draft doc ready

You need to know how much money everyone has left.  You need to know what everyone’s max bid is to be able to fill out the rest of their roster.  This is really important and hopefully this initial draft doc can become your league’s official roster doc once the draft is over.

Have an often revised spreadsheet of rosters from draft day forward

You want to have a very clean list of every team’s players and costs.  This should be updated regularly.  This again allows for transparency and prevents any arguments over how much a guy costs or who drafted whom.  This is another document that would be good to make in google sheets and link on your home page.  It should also help prevent trade rape caused by mistakenly or lying about player values.

Have a sticky thread or link to a doc for suggested rule changes that you can vote on the following year

You might be really attached to your league if you created it.  Well I’ve got news for you; it’s not perfect.  Be open to the idea of making adjustments based on experience and suggestions from your league mates.

Maybe relievers are worth too much, or maybe you decide you want to make it 5 keepers instead of 3.  It’s nice to have a dedicated repository for ideas and you can follow-up with a forum before the next year’s draft.  No league is perfect, but I believe the ones that evolve tend to be better than those that stay static.

This next section is going to go into some specific questions you need to think about with keeper and dynasty leagues.

Auction or Snake?

This is important for a pretty obvious reason.  Keepers in snake are usually retained based on some kind of round value whereas auction keepers have a dollar value attached.  Standard auctions are usually based on a $260 budget, but there are obviously some custom auctions where that number is higher or lower.

How many keepers?

This is a pretty important question that dictates the amount of turnover in your league.  Do you want to just keep one or two guys?  Do you want there to be 10 or more keepers like there are in a dynasty format? Or is there a number in between that you want to do?

The more keepers that your league has, the less turnover there will be in the league.  It also devalues the draft a little bit.  If there’s a team with Trout, Correa, Kershaw, and Mookie Betts – that team is going to dominate for some time.   Limiting keepers makes the draft matter a lot more and allows for more year to year volatility.

Dynasty leagues are awesome and I love them.  There’s nothing better than starting your team with a bonafide stud at the fraction of the cost.  I personally love the draft even more.  Try to weigh which you like more or pick a middle ground.  5-7 keepers is a beautiful mix between a standard re-draft and a dynasty league. If you’re not sure, start out low and increase by a set number each year until you find your happy medium.

Inflation and term limits

Can you just keep the same guys over and over with no penalty?  Or is there inflation and/or some kind of limit to how long you can keep each guy?

I personally love the idea of inflation for keepers.  If you do snake then you can add a round or two for each year the team keeps him.  For example, maybe George Springer was a 5th round pick in 2015.  So he would’ve been kept as a 4th round pick if he was retained last year and could be kept as a 3rd rounder for this season.

With auction, you can just add a few dollars for every year someone is kept.  I’ve seen increments of $1-10 per year.  I think $2-5 is kind of the sweet spot.  That way you are still paying a small tax for keeping someone, but you can still get great value if you got in on a player early on.  You can also make it so that single year keepers suffer no inflation, and inflation only applies to multi-year contracts.

Waiver pickups

  • Can waiver pickups be kept?
  • Is there a cutoff for when you have to pick someone up by to keep them?
  • What kind of value are the waiver adds to be kept at?
  • Are there injury restrictions on players?
  • Is there a games played minimum to keep a player, or can you stash a player that’s recovering from Tommy John or some other injury?

There are just some of the questions that need to be addressed early.

If there is no limit on games played to keep someone, then you might want to add a DL slot or two.  The last thing you want is some contender having to drop Carlos Carrasco to make a title run and some other team gets a star for free.  On the same token, don’t recommend unlimited DL slots if this is the case either.  I would say 2-3 is ideal.


  • Is there a prospect draft, or are you drafting the rookies right in the draft like you would in a standard re-draft league?  
  • Are there farm system slots?  
  • How long can you keep a minor leaguer in your farm system once they’re called up?
  • Can you stash a prospect off of waivers that hasn’t played in the majors yet, or do you need to wait until he’s called up ?
  • Is there a maximum amount of prospects that you can have in any one farm system?  
  • Can you trade prospect picks or minor leaguers?

Just like with the waiver wire, there are a number of questions that you will need to consider before you begin the season.

International players

This ties into rookies above.  Are international players eligible to be drafted in the prospect draft (if you have one), or can you simply going to draft them in the normal draft?

Trading Contracts

What effect does trading have on the contract of the players traded? Does that restart inflation or does it carry on as normal? Can the new owner even keep the player if the last owner already kept him?  These are important things that need to be made very clear in your league bylaws.  

Can you subsidize a contract?  Maybe you wanted to unload an expensive Giancarlo Stanton last year and were able to do it by agreeing to pay $10 of his keeper cost.  Is that something you want to allow?

Uneven Trades

I mean this both in regards to both the number of players as well as the level of talent exchanged.  Can team A trade 5 prospects for a superstar?  Does the league get to vote on these trades or is the veto a “commissioner only” tool?

Also, is it okay for a team to tank?  If a team is rebuilding, are they allowed to dump their assets for cheaper, younger players, prospects, and picks?

Personally, I think a team should be able to do whatever they want to do in an effort to rebuild.  I do like the idea of incentivizing a team not to finish last, though.  This helps preserve the integrity of the eventual champ by keeping the league competitive til the end.  Maybe you do a consolation ladder where the winner of that bracket gets the 1st prospect pick or first pick in the actual draft if you’re doing snake.  Maybe they can even get an extra keeper slot.   Anything that keeps the bottom feeders in it til the end is a good thing

Salary Cap

Auction leagues generally have a cap of $260 for the draft.  Is this cap to be enforced during the season as well?  This will require cap balancing during in-season trades.  

Another thing you can do is incur a luxury tax of some sort.  If people go more than a certain percentage over the allotted $260 (or custom number) then they lose a pick in the prospect draft.  You can also punish them by taking draft dollars away for next year’s auction. I’ve seen the in-season cap work okay, and it’s a nice wrinkle for advanced league, but I think it’s more of a pain that it’s worth.  


Those are the basics to get you started.  Do you have any additional questions on new dynasty leagues, or even one about an existing one?  Leave your comments below and I’ll try to help you the best I can.


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Mike Sheehan

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Comedian, Powerlifter, and most importantly a Cum Laude graduate of the fantasy baseball school of hard knocks. Double major in points and categories with a minor in roto. Happy to be doing my Postgraduate work here at the Fantasy Assembly.