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How to Decide Who to Keep in Your Fantasy Baseball Keeper or Dynasty League

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

I’m indecisive. 

Ask my wife. It drives her absolutely crazy. Whether it’s what to watch, which restaurant to go to, or even whose car we want to take when we go out.

I. Hate. Making. Decisions.

I’ve written before about making trades, and how I’m not afraid to lose a trade, but when I’m sitting there, put on the spot, making a call is tough for me.

That’s why I enjoy slow drafts so much. I can take more than 60 seconds to evaluate my options and who I want to take. 

If I’m in a regular draft, and the top tier is comprised of four players, I want the fourth pick. I’ll let the others in my league make the decision for me.

So, as you can imagine, when it comes to making decisions for who I’m going to keep in my keeper and dynasty leagues, I put a lot of thought into it and explore every factor imaginable before making a decision.

Before we get to the meat, let’s season it a bit like we typically do. It’s going to be impossible to touch on every format or type of league here with this advice because there are thousands and thousands of ways you can construct your league. We’ll keep these pretty high-level and try to help out as many people as possible.

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Understand your league rules.

This sounds easy, but it’s looked over so often. Make sure you know how many players you can keep, and if it’s a hard-set rule or if it’s “up to” so many players. It makes a big difference.

Understand the cost associated with each player. That could be their actual auction value if you play in a league with contracts, or it could be their round cost.

If it’s the former, make sure that you have your scoring settings completely ready and utilize the FanGraphs auction calculator. You can plug in your league scoring and settings, and it will give you the value of that player. It’s a nice frame of reference to see what you are paying and what you should be paying. Of course, if your scoring leans pitching, you’ll need to adjust for the acquisition cost to get a top-tier SP.

Keeper length.

While I play in a league where you can keep any four players you want year to year for as long as you want, I prefer leagues to have a limit of how long you can keep a player to force tough decisions and to keep resupplying the talent pool. 

That comes into play when you’re deciding who to keep. You have to project, a bit, and decide if the player you can keep three more years who have shown flashes of their potential and is on the track to superstardom is worth the gamble over one or two years over the proven, steady veteran.

I ran into this issue heading into the 2019 season. I could have kept a 21st rounder in Fernando Tatis or an 18th rounder in Nick Senzel vs. a 13th rounder in Matt Chapman. I took Senzel, because it wasn’t clear that Tatis would make the team out of Spring Training

I. Hate. Making. Decisions.

What to look at.

I, personally, like to look at a track record over recent numbers. Recency bias is one hell of a drug, so I’d prefer to dig in more to a three-year trend of a player when evaluating my options. Of course, there will be those pop-up guys who take the league by storm, such as Aristides Aquino in 2019, where there isn’t a lot of history to take into account. There, it becomes a situation where you have to compare him to the other options that you have.

For the younger guys, pedigree plays a big part. Late bloomers, like Jose Bautista, Jeff McNeil, and Whit Merrifield exist, but looking at prospect pedigree can be indicative when making your decision.

Path to playing time

This is huge. Opportunity breeds success. It can be applied anywhere, but especially in fantasy. It’s why it’s so maddening when the real-life team will sign an aging, washed up veteran who blocks a young guy with a pedigree for playing time.

I’m sorry, Dave Roberts, but if Alex Wood is blocking Dustin May for innings, we are all going to riot.

It’s hard to keep a guy in a league with minimal keepers if there isn’t an immediate clear path. They’ll not only not help you in the immediate future, but their future value for trades will go down, too, due to the fact that they are stuck.

Hello, Clint Frazier.

Overvaluing prospects

In a deep dynasty league, you need to keep the present and future in mind at all times to succeed. But every dynasty league that I’ve been in has that one prospect hound who is willing to overpay with the current big thing for the next big thing.

I try to cash out here when I can, flipping a top prospect for a guy who is still young and can help me in the present and future. It’s nice to dream on the future, but it’s even better to acquire someone who we have seen succeed at this level.

Weighing hitters vs. pitchers

My general rule of thumb is to go heavy with hitters in keeper and dynasty leagues. They hold their value longer, the year-to-year production is more predictive, and the injury risk is a lot lower.

It’s getting more and more difficult to take that approach consistently, as the landscape has shifted more toward pitchers having elevated value. Also, if you haven’t noticed, outside of catcher, the year-to-year positions have been stocked with a lot of value. There’s no shortage of great shortstops anymore, and trying to rank a top 20 at third base seems offensive, because you’re leaving so many studs off.

I still lean hitters to pitchers, but more of an 80/20 split for my keepers. 

If it’s a pitching prospect, I’m unlikely to keep them, because there is just so much that can go wrong. The only way that I consider doing that is if I have to keep seven or more players, and the pitcher is at least advanced in Double-A and expected to debut within the next season.

Future value

This is the hard one to project. You can take the past three-year stats for a player and apply them, but how are they going to age, and will they continue performing at this level? You want to accrue assets that will help you win, but you also want to have assets that you can flip if need be. This is where I’d lean the young prospect over the proven guy. Say you can only keep five, and you have to choose between Josh Donaldson and Alec Bohm. I’m probably keeping Bohm here for the upside and long-term play.

Expiring contracts

For those in dynasty leagues with expiring contracts that you can renew, this is always a tough decision. More times than not, I’ll go one or two years on a pitcher, just because so much can change with them. Remember how dominant Zack Godley was two years ago? Imagine extending him on an expiring deal that year. Yikes.

Unless they are a top 50 player, I’d avoid extending a player for the maximum amount of years. I tend to play conservative, so that I’m not stuck with an immovable piece.

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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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