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Tips for Starting a Keeper/Dynasty League from Scratch (Fantasy Baseball)

by Michael Waterloo | @MichaelWaterloo | Featured Writer
Jan 20, 2020

Maybe you play in just one league. Maybe you have multiple, but you just can’t get enough. Whether you’re new to dynasty and keeper leagues, or if you’re a seasoned vet, there are aspects of setting up your league at the beginning that you’re sure to overlook.

That’s what we are here to help, and we’re here to learn with you.

We’re going to have this serve as a step-by-step guide to starting a long-term league from scratch, and feel free to shout at me on Twitter – @MichaelWaterloo – if I leave anything out that we can add-in.

Let’s get to it.

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In order to have a good league, you have to find good league mates. The first step I would do is to find someone you know who is just as invested in fantasy baseball as you are, and see if they’d be willing to help you run the league. As soon as you get that person, the two of you can decide the format that you’re playing, an idea of how many teams you want, and if it’s going to be a keeper league where you keep a limited amount of players, or if it’s going to be a full-fledged dynasty league where you keep the vast majority of your players for a period of time.

Before you recruit the rest of the league, it’s time, first, to build out a constitution with your co-commissioner. 


This should be your league Bible, but trust me, you’re going to forget something when you’re drafting it. Honestly, just accept it. 

I recently started a fresh dynasty basketball league, and I compared the constitution to other leagues that I’m in, read it over four times, shared it around with the league, and had a co-commish review it, and by Week 10, there was a question. And then there was another.

Just do your best with it, but be open to clarifying what’s in there and addressing questions that your league has after it’s circulated.

Here are some of the things that your league constitution should cover:

  • Number of teams: Self-explanatory, but list the teams and contact info.
  • Scoring format of the league: Go in-depth here. If it’s roto, is it traditional roto or are there other categories at play? If it’s a points league, do a full breakdown of the scoring. 
  • Keeper limit: This is huge. If it’s a keeper league, make sure that you put in not just how many players you can keep, but the retainer cost to keep them. Do you lose a round of value? Can you keep them forever or only a certain amount of time? If it’s dynasty, how many players can you keep, and do you have to keep that many, or is it up to a certain amount? How do prospects work? Give as much detail as possible.
  • Draft rules: If there are minor leaguers in play, will there be a separate draft for them, or are they all included in one? If you have a First-Year Player Draft, are international signings included? How is the draft order determined? Can draft picks be traded?
  • Trades: How far in advance can draft picks be dealt? When’s the trade deadline? Do you have trade vetoes?
  • Money: What’s the buy-in? How many teams can finish in the money, and what are the payouts? Where is the money held?
  • Playoffs: How many teams make the playoffs? Is there a consolation bracket? What are the tiebreakers to get into the playoffs, and what are the tiebreakers in the playoffs? Is there reseeding within the playoffs?
  • Free agency: How is the league set up for free agency? Do you have FAAB, or are you using an ordered claim model? How often do waivers run?
  • Lineup: Do all of the spots need to be filled? Are there any starts limits? Is this a weekly or a daily lineup league? What causes a lineup to be illegal?

It seems like a lot and it seems annoying, but it’s all very important to include from the beginning.

Recruitment Part Two

So now that you have a partner in crime, and now that the constitution is drafted, it’s time to fill the league. Ideally, you’d be able to fill it with people that you or your co-commish know so that you can vouch for the members. But that’s not always the case.

There are groups that I’ve mentioned in the past such as Baseball 365 on Facebook or forums on Rotoworld that are filled with people looking to join leagues. Those are good places to look if you either want to join a league or if you want people interested in yours. 

Make sure you vet them, though. Don’t just give them the keys to the kingdom. Make sure they see the constitution, understand the scoring, and are on board with it. 

Tips for Success

Here are a couple of things to keep in mind in the early stages of setting up the league that I’ve found to be very helpful.

  • Be flexible and communicative: Talk to the members and get their input on the scoring or the setup. See what works and what doesn’t work. The format or settings that you have may seem like they are the best, but talk it out with the group and see where there are areas to improve at. You should put the long-term success of the league above your ego.
  • Establish a keeper length: Whether it’s keeper or dynasty, you should have some sort of length. It cycles the players back into the pool and it helps maintain competitive balance. Instituting a keeper penalty is a good idea, too. If you draft a guy in the 13th round, if you want to keep him the following round, he becomes a 12th or 11th rounder. Or, if you use salaries, come up with a formula where if you decide to extend a player, the cost goes up for them. If you extend them five years, the increased cost per year will be less than if you extend them just one or two years. 
  • Pay for two years in advance: Trust me, it works. You should want to maintain a very low level of turnover in your long-term league. It’s going to happen because life gets in the way. That’s fine. But when you start losing three to four players each year, the league is in jeopardy. At the offset, if you’re thinking of a $50 league, have each member pay $100 to cover the first two years. From there, you are always paying for the following year. This helps to limit the turnover in league managers, but it also ensures that any new manager who joins won’t be screwed over by a team being in shambles.
  • Hold winter meetings every year: Talk to the group. Get ideas for ways to improve the league, and put them up to a vote. 
  • Don’t have vetoes: Just don’t. Trades can look lopsided in keeper or dynasty leagues, but that’s OK. Allow teams to manage their teams how they choose.
  • Only use one catcher: We get it, two-catcher players. You’re an extreme fantasy player. It’s hard enough finding value with one catcher let alone forcing a team to have two. 
  • Give incentives to owners: If you win the consolation bracket, there should be a reward. It can be maybe half of your buy-in back, or it can be allowing that team to pick where they want to draft from the following year. The same thing goes for the team that was most dominant in the regular season – if it’s a head-to-head league. The goal is to make the playoffs. Once you get in, anything can happen. Give the regular-season winner a reward for kicking ass for a long stretch. 

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Michael Waterloo is a featured writer at FantasyPros. For more from Michael, check out his archive and follow him @MichaelWaterloo.