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Midseason Dynasty Rebuilding Strategy

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Midseason Dynasty Rebuilding Strategy

“The best-laid plans of mice and men oft’ go awry” - Robert Burns

We’re at a point in the calendar now where the fate of your dynasty roster is probably rather apparent.

Even some of the better squads inevitably suffer as time unfolds. Injuries to key players happen, or you make a handful of lousy start/sit calls that cost you a few Ws. That’s the game we signed up to play.

So, maybe this season isn’t the championship run you’d hoped for.

Pivoting from trying to contend into rebuilding mid-year can be tricky, and the worst thing you can do is take it too far and end up screwing yourself out of competition for a much longer window than anticipated.

If this is a journey you’re considering going down, let us help guide you and talk about midseason rebuilding, including featured advice from Fantasy Points contributor and host of the Dynasty Points podcast Thomas Tipple.

Think Before You Sell: Understanding When To Pivot

Dynasty is a game of different windows.

Understanding where your team is on the winning timeline isn’t exclusive to the offseason. Even in a rebuild, you still want to “win” at some relatively defined point.

However, knowing when to make foundational directional choices is where the game becomes complicated. Heck, I’d go as far as to say your ability to be present and mindful during the season is even more important than anything you do in the non-point scoring portion of the calendar.

The last thing any manager should want to do is give up for no reason, right?

Before you take any sort of leap, let’s discuss some indicators that will inform your ultimate decision:

What factors should you consider before folding your season and selling off assets?

Tipple: “The first thing I am looking at is if my roster is high value/high production, mid value, or neither. To do that, we have to look at a few things:

  • How flush am I with rookie draft picks?

  • What is my team's ‘points for’ (PF) average?

  • Where am I compared to the rest of the league?

We know that if your team is 2-5, it is generally over, but the record is not an immediate indicator of selling ALL your assets. So, if your team is high in PF, there’s definitely some room to make moves. If your team is 2-5 and low in PF, it is time to start stripping it down more to the core.”

In plain terms, managers must be honest when assessing their team.

Knowing how many assets you have and how well your team is performing will give you more answers than any minute details you may sometimes lose track of.

Deciding to compete in July and sticking with it when a roster falls apart in mid-October is just unwise. The caveat here is that if your record is poor, but the roster you have is putting up a lot of points every week, that may be a symptom of having some bad luck with head-to-head matchups.

If you’re generally doing well, are still relatively competitive, and have the assets to make moves to boost your odds, then keep going. If not, call a spade a spade; it’s over for the season, and that’s okay!

Making The Pivot: Who (and What) To Target In Trades

Okay, so we’ve decided that now is the time to sell and rebuild — the easy part is out of the way.

But now what?

Dynasty managers often make mistakes in the subsequent steps of this pivot, so follow these next sections carefully.

Now it’s time to discuss what types of deals you should be making and which ideas are best to avoid:

Are there any sorts of deals you should look to target or avoid? (kinds of assets you get in return, give away, etc.)

Tipple: “One thing people do that I really don’t like is taking your team down to just draft picks. If a team wants to rebuild, you do not have to trade your elite young wide receivers for a few first-round rookie picks. You don’t have to move young QBs to get more picks.

Why? Because with those picks, you’re hoping to land those elite players anyway… It is okay to rebuild and have players on your roster.”

This is a point that readers should really sit down and absorb. If I could scream this at you through the digital screen you’re reading this on, I would: it’s more than okay to keep young, ascending assets while you’re trying to rebuild.

That is how most real-life sports teams perform rebuilds.

Look to the MLB for some of the best examples of how rebuilding and keeping talent around can work. The 2016 Chicago Cubs won their first World Series in 107 years, in some part, by keeping foundational pieces like starting pitcher Jake Arrieta and infielder Javier Baez around even while the team was still working toward contention.

Granted, that’s an incomplete telling of that story, and the immediacy with which NFL players impact their teams and in fantasy is much different than in baseball, but the principle of it all still applies.

A wide receiver or quarterback in their second or third year will still be helpful to you in another couple of seasons when you’re ready to compete.

Drake London will be just 25 years old in 2026. Ja’Marr Chase would only be 26. Even quarterback stalwart Josh Allen is still relatively young at age 30 by the time your two-year window opens, and with how long QBs tend to play in the modern day, that’s not all that bad either.

Of course, if you only have one definitively vital asset that will net quality return, that’s a different story based on personal discretion, but the point stands. These picks you want are meant to be used to find these stud players, so don’t move them just because this year stinks.

Tipple also points out that a common parallel between baseball and dynasty fantasy football is the concept of acquiring younger players who may gain value down the line with increased opportunity:

“I also want a player in deals as much as possible. Instead of getting, say, three second-rounders, try and get a second and a decent player to either ship later or that will just accrue value. For example, I’d rather have two second-round picks and Audric Estime than three second-round picks.”

Consider how a baseball team will trade a dominant starting pitcher to a contender and end up with three to five prospects in return.

The players at the lowest minor league levels in these deals are essentially rookie draft picks in dynasty; they represent a future asset far away from helping you compete. Those in AA or AAA are practically equivalent to a young NFL player temporarily buried on their depth chart.

Is there a guarantee that this athlete gets the call and succeeds for a long time? No, but once their opportunity is open to them, a selling window in dynasty also opens, thus enabling you to reap additional benefits of a completely separate trade you made X months/years ago.

Cashing in all your tangible assets for draft picks effectively only buys lottery tickets. You might win a bit of money here and there, but unless you have some sort of master plan to accumulate the entire first round and a half of an upcoming rookie draft, it’s just an unnecessary gamble to only acquire draft picks.

Now also feels like a good time to remind people that even the “winning” teams are just as prone to falling out of it as you are, be it through injuries to stars of their own or what have you.

As Tipple reminds us, “I do not think you need a “window” to compete because many things change too quickly. A team that is “competing” or has a “late projected” first in Week 1 is two stubbed toes and a bad route run from being in the bottom-five if they don’t have assets to move because they “went all in.”

“Instead, you want to have enough value that if you get into a situation where your young players pop and put you in position, you can make the moves necessary to start competing immediately.”

Be sure to be mindful of that aspect as well.

At some point during your rebuild, you will want the assets to be able to buy veteran players to contribute to your efforts, much in the same way the Cubs gave infielder Ben Zobrist a sizable four-year contract at the beginning of 2016 or when the team traded for center fielder Dexter Fowler in 2015 ahead of their eventual title.

The winner you build will come from within (the players you draft or find on waivers) just as much as from outside sources (trading with your league mates).

Final Thoughts and Parting Advice

So far, we’ve learned that:

  • Teams who aren’t scoring points at a high rate are the best rebuild candidates.

  • Holding onto players and certain draft assets that will help you is okay.

  • The rookie picks you acquire are helpful, but don’t forget about adding young players with increased value potential to be part of any trade return, too.

Let’s close out here by focusing some effort on acquiring draft picks and any other final pieces of wisdom to consider:

How do you value future draft picks, and how far out are you willing to accept picks for premium assets?

Tipple: “I will always take first-round picks because they are the most liquid assets in the game. I want the future assets from everyone, and I am willing to lose some points on my roster from vets to get it.

I do not think we should be trading high-tier players for picks multiple years because if you trade a 25-year-old wide receiver for a ‘27 1st, that player likely still has first-round value in ‘27. You aren’t gaining any value. You’re just kicking it down the road.

Every year, people say a draft class is bad or good, but people still value their picks highly on draft day when push comes to shove. We should use that to our advantage. If someone thinks the class of ‘27 is bad and it devalues to pick… go get that pick. Someone in the league will value it enough to trade for more than what you did a few years later.”

Another notable piece of advice from my conversation with Tipple also overlaps with the “Productive Struggle” article I had published with thoughts from originator Ryan McDowell: *** DO NOT FALL INTO A PERMANENT REBUILD ***

It’s about the most wasteful thing you can do, and avoiding doing so is something I gather any reader can interpret based on all the things we’ve recommended not to do in this article and from my conversation with McDowell.

As Tipple reiterates in this interview, At some point, you need to win and to win. It takes trading for the right vets at the right time.”

Don’t lose sight of the ultimate goal. You do want to win at some point. But if you’re having a hard time making trades, it might be time to look inward:

“If you can’t get trades done, but everyone else in your league can, the problem is not your league. The problem is you,” warns Tipple.

“The market can only take you so far when the micro market of your league is telling you how they value players. We can’t make people see our point of view, and if you want to get deals done, you have to adjust your trade tactics. When you do that, you can stop playing fantasy football for clicks, and you start playing to increase the money in your pocket.”

We hope this exercise has provided you with the tips and tools required to make a path toward a successful rebuild.

May your efforts net you a title (eventually).

C.H. Herms is a fantasy football analyst, bringing years of prior experience from his weekly dynasty articles at Draft Sharks and contributions at FantasyPros and The 33rd Team. His journey from a heavy baseball analytics nerd to a passionate fantasy football fan has allowed him to combine his love for sports analysis with storytelling, offering unique insights to the fantasy community.