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Keeper/Dynasty Strategy with a Low Number of Premium Picks (Fantasy Baseball)

by Michael Waterloo | @MichaelWaterloo | Featured Writer
May 5, 2020

Contenders who have few picks in a dynasty draft must alter their approach.

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So you pushed in the chips and went for it. Good for you. Flags fly forever, right? Enjoy the well-deserved praise and adoration from your league mates, but after a few days, reality sets in.

Sure, you cashed out, won the title, and achieved the pinnacle of your fantasy league. But looking at your roster now, you may have your work cut out for you moving forward.

Pushing for a title in a dynasty or keeper league usually takes a few years of planning. That’s what makes dynasty and keeper leagues so great. When it’s time to compete, you’re pulling out all the stops, including trading younger players and future draft picks for veterans who can help you win now.

Now, since every keeper and dynasty league is different, it’s hard to write an all-encompassing article about how dealing those young players can change your strategy for the next few years. We can, however, write about how dealing draft picks for the following year will change your approach.

This has some caveats, too, of course. We don’t know how many players you can retain from year to year, and we don’t know the skill level of those players. We have no idea how player contracts work, either, so we are going to simplify this as much as possible for those who dealt away their early picks for the upcoming season.

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League size and depth matters

As is the case with nearly every strategy in fantasy baseball, you need to know your league. If it’s easy to stream throughout the season and you’re able to find good value on the waiver wire, it may change your draft approach with fewer top picks. If your league is on the shallower side (20-23 players), that could also allow you to weigh whether or not you want to lean toward upside or safety with the picks that you do have.

It’s important to look at FAAB bids from the prior few seasons, if that info is available, to see how those in your league approach bidding for free agents. If they are aggressive, you may need to reach for a player with high upside sooner in your draft, but if they want to wait and see, you should be able to jump the proverbial gun on them with your in-season management. 

Lean toward safety

In a typical re-draft league, your goal is to leave the draft with the most value possible with each pick. With your early picks, you want a combination of high-floor and high-ceiling players who won’t hurt you or bust early. Remember, drafting someone in the first round who returns second-round value is still OK.

When you don’t have those early-round picks, though, you really need to maximize your value with each selection.

Typically, if you go safe early on, you’re able to balance that safety with high-upside picks in the middle and end of the draft. But with fewer picks in the early going, you need to go with players who you know — barring injury — will give you the production that you need. That means if you’re deciding between a player like Luis Castillo and Aaron Nola, you need to go with Nola, even if he doesn’t have quite the upside of someone like Castillo.

Make each pick count. Assuming that you had to acquire a pick back in the deal where you traded your early draft picks, you can reach for some upside guys with those later picks in hopes that they click. 

Trade your early picks every year

If you build a solid enough foundation with the picks that you do have, and assuming that your keepers are good enough, you need to try to go for it again. You should get a feel for what the other teams in the league are doing and what their strategies are. If, say, at the quarter-point in the season you are in the playoff hunt, try to acquire slow starters for cheap that you can plug into your roster in hopes of a turnaround.

If you’re in the thick of things at the halfway point of the season, dangle your picks out again. It’s important to either go for it altogether or punt on the season. You don’t want to be stuck in the middle of the pack.

Target bounce-back candidates

Once you lay your foundation of good players who have a steady floor, start to look at players who have a track record of success, but may have had an off year for one reason or another. 

Remember, fantasy baseball is a lot of “what have you done for me lately,” so take advantage of those in this mindset. You may be able to find a player who was going in the Round 5 or Round 6 range a year ago toward the end of the draft. If they return to form, you get a boost. If not, it’s easy to cut them and not look back.

Set an early-round pick cap if you’re the commissioner 

One way to succeed in a keeper league and maintain competitive balance is to limit the number of early picks (or which picks) that can be dealt. If you’re worried about turnover in your league, make it a rule that a team has to pay half of the buy-in if they trade more than three of their first eight picks. That way, if the team decides to leave the league, the next person who takes over isn’t stuck with a broken roster. 

You can also exclude first- and second-round picks from trades so that every team is able to have some semblance of a foundation each year. If this is the case, and you’re a contending team, trade as many of your third, fourth, fifth, etc. picks as it takes to make a push for the title. 

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

Dynasty, Featured, Featured Link, MLB, Prospects, Strategy