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How to Smoothly Expand Your Fantasy Baseball Keeper or Dynasty League

by Michael Waterloo | @MichaelWaterloo | Featured Writer
Jan 22, 2020

The best part about keeper and dynasty leagues — successful ones, at least — is that they have years and years of history behind them. You have the same core group of people, hopefully at least an 80-90 percent retention rate, and people who are playing because they enjoy it and not just to try to win money.

But as time evolves, the game =- both real and fantasy — evolves. So we, too, must change with it. Replace saves with saves plus holds. Replace wins with quality starts. Still using average? Use OBP instead. 

But another way to change is to expand your league by adding another owner (if roto) or two (if head-to-head). It’s easier said than done, right?

Here are a few ways to tackle league expansion in both your keeper and dynasty leagues.

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Familiarity
What I’ve found to be successful in expanding my keeper leagues is to try to make the decision as soon as possible, and get the new manager up to speed with the league rules and constitution. 

It’s a good idea to give the new manager some time to get familiar, too, before officially announcing that they joined the league. Far too many times, the existing managers, as great as they might be, will try to get a leg-up and subconsciously – or consciously – take advantage of the new person.

Don’t let this happen. Allow them to review everything and ask as many questions as they have. Especially so if it’s a larger dynasty league where you have separate drafts, contract lengths, auctions, etc. 

Set them up for success.

Make Players Available
It can get tricky here, especially the deeper the league is and if you have contracts involved. If it’s a general keeper league where you keep four to five players, what I would do is have the current managers all pick their keepers, and then the new managers get to pick from the remaining players on all of the rosters to fill out their keepers.  

If it’s a dynasty league, it gets a little bit trickier. The player pool shrinks, putting the new manager at a disadvantage. If there’s a limit of players you can keep (say, 15 big leaguers, 15 MILB of your 40-man roster), I’d have the current managers mark 27 players that are safe and then have a Rule 5-type draft between the new managers to fill out their rosters.

If there are player limits, meaning you can only keep a player for up to three or four years, consider restarting the clock on the players that the new managers pick. They are already going to be picking from the leftovers, so allow them to keep someone who is on an expiring contract for the max three or four years by resetting the clock. 

If they are taking on bad contracts when they join, maybe consider cutting those in half or giving them the ability to start fresh with contracts before starting. 

Start at the Top
If you have a rookie draft, the new managers get the top picks automatically. More than likely in a dynasty league, they are going to have to rebuild, so allow them to get a head start by taking the top available player instead of putting them at the end of the draft.

They should also get the first pick in the regular draft, or if it’s an auction draft, allot them some extra cash so that they are able to even things up a bit.

With this, I wouldn’t be opposed to adding two supplemental picks after the first and second round are over, either. If this is a dynasty with a fresh first-year player draft or international draft, then give them an extra top 20 player to add to their farm for their rebuild. It may not seem like much, but they could land the next Vladimir Guerrero Jr., Fernando Tatis, Wander Franco, or Bo Bichette with that pick. 

Monetary Concerns
This honestly needs to be put up to a vote with the rest of the league. If it’s a smaller league where there’s plenty of talent available, then the new team should pay its dues like everyone else if we are talking expansion. If they are taking over a terrible team that has been gutted by a past owner, I’m OK allowing the team to play for free in the first year.

But if we are talking dynasty here, where there are hundreds and hundreds of players being kept, leaving a bunch of fourth and fifth outfielders and starting pitchers as the top available options, I’d lean giving a pass on the entry fee for the first year. 

Vet the New Managers
We’ve given tips on how to make the new managers feel at home, but don’t forget about upholding the standard that you’ve set for your league. I’ve mentioned different Facebook groups to use to find leagues (Baseball 365 is the best, by far) and forums on Rotoworld and other sites are great, too. 

My first approach, though, is to check with other league members and see if they have any friends or recommendations for someone who may be a good fit. Some are leery to do it, which I get because if the new manager ends up being a poor one, they don’t want it to reflect poorly on them.

Whether the new manager comes from a forum or from a friend, take the time to chat with them a bit. See why they want to join the league. It can be just for fun or for a new challenge. Not everyone has to be an NFBC high-stakes champion. Just make sure the person seems like they’ll be active and they’ll be a good fit for the culture that you’ve established. 

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

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