Dynasty Compass | Boosting Your Win-now Lineup

Using our compass metaphor, the West is home to Win-now teams. Jeff offers some strategies for dynasty managers looking for late-season boosts to their lineups.

🧩 Key Takeaways

• What a Starter Boost is
• How Bench Boosts fit
• What win-now teams can sell (picks, broken toys, prospects, surplus), 
• What they should buy (rentals, certainty), and
• When to pull back and pivot when winning now may not be the best strategy.

Win Now = Controlled Aggression. Smart upgrades to starting lineups lead to championships.

Transcript

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Dynasty Compass - Episode 13 "Boosting Your Win-now Lineup"

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You are a contender. You're not just fighting for a playoff spot, but for a high seed, a first-round bye, any playoff advantage you can earn. A championship is in sight, but you're not quite there. You need some upgrades. You need a boost to your lineup. Welcome to the West, Win Now, all in for a title, next on Dynasty Compass.

Welcome to Dynasty Compass. Thank you so much for joining me today. I am Jeff Blaylock, the Other Jeff B from Footballguys. I want to thank you so much for listening, for watching, for all your comments, your likes, your shares. It's all very, very helpful to me. It helps me continue this podcast. 

Today, we are gonna take a look at the West. Now the compass has been our metaphor all season long for defining a team's strategic direction. North is our ultimate goal. That is perennial contention, but today we're going to forego that possibility to win now. We are headed to the West, and in the West, we are willing to give up future possibilities for points right now.

We're gonna lean heavily into that win-now mindset that prioritizes winning a title this year over becoming a regular contender. 

Perhaps you've been a contender for years, but you haven't won the championship. Maybe you have an overperforming roster, you're at the top of the standings, and you're not merely content to wait and see what happens. Or maybe you have an aging roster and your championship window is closing quickly. Perhaps you're tired of being an ATM for the rest of your league, and you view this as your best chance to win the cash. The point is, however you got here, this is your year to go all in for a championship. 

We are building a short, perhaps one-year only, championship window in lieu of perennial contention. We're willing to sacrifice future success to win that trophy now. All of our assets are on the table to improve our starting lineup. Nothing else generates points and fantasy than that starting lineup. Points win fantasy games just like they do real ones. 

If a player or an asset is not generating points, it's tradable. It's expendable. That could be your next man ups, that could be your developing talents, that could be your draft picks. Now, last week I talked about trades involving draft picks as being a choice of possibilities or of points. There's only one answer to that dilemma if you're in the West, and that is points. 

"Possibilities or points" isn't really a question for you if you are trying to win now. The question instead is, "How many points do I need to add to my starting lineup each week?" We need to turn the potential that we have on our roster, particularly those draft picks, into points. If we are going to win now, we need a boost, particularly in that starting lineup. I'm going to refer to it as a Starter Boost.

This is a net addition of weekly points to your starting lineup. Ideally, it would be like adding a whole extra starter to your lineup, like having an 11th starter in a lineup of 10 players. So you're looking to add at least the average of your regular starting lineup – the average points of players' scores.

Now, ideally, again, we're in the ideals here to start. Ideally, you're replacing your lowest-scoring starter, but that's not always possible. The truth is, it doesn't actually matter who you replace in your starting lineup, as long as the result is the same: a net increase in your lineup score. However, you may have to buy even more of a boost, more of an upgrade, to replace someone who is not dragging down your average.

The other kind of boost that we can use here as a win-now team, but not nearly as critical as a Starter Boost, is what I would call a Bench Boost. This adds starter-quality depth that you use only when needed. It doesn't help your typical lineup. That point total is going to remain the same, but it would help your lineup if one of your starters were to miss time at the worst possible time: during the fantasy playoffs. So there is some value to be gained by boosting your bench, even if it doesn't translate into your weekly scores unless someone gets hurt. 

Now for purposes of this discussion and this episode, we're going to use Startup Boosts as our unit of measure. And you may be thinking, well, why wouldn't you just use points because that's what we're trying to score? Well, there's a very simple reason for that. Every league has different scoring rules and different lineup configurations, so adding a certain number of points, let's say 10, to your lineup, has different impacts from league to league to league. And so an addition of 10 points in one league is going to be a lot less expensive than adding it in another.

So instead of looking at it from a perspective of points, let's make it agnostic to what your league settings are, and that's what a Startup Boost is. A full Startup Boost adds the equivalent of an extra starter, so that means it equals the average score of the players in your current lineup. A half Starter Boost adds, well half of that, and a quarter Starter Boost adds a quarter of that.

Now to figure out what a Starter Boost is for your league is gonna require a little bit of math. I promise, it's just a very, very little bit of math. We're gonna divide the average number of points your lineup, scores from week to week, and then divide that by the number of players that you have in your lineup.

Now, if you are in a league that uses defenses or kickers, and I'm sorry if you are, but if you are, go ahead and exclude them from the calculation. They tend to be much lower scoring assets than some of your other players. The exception to this exception is if you are in a league where you can flex either position, so you can flex a kicker in, in which case you want to go ahead and include them in your calculation.

So for a lineup that averages 150 points and has 10 starters, a full Starter Boost would be a net gain of 15 points up to 165 per week. A half Starter Boost would be seven and a half points. We'll round that up to 158 for ease of use, and a quarter is 3.75 points rounded up again to 154. 

So that's what you're looking for: players that provide those level of boosts into your starting lineup. When you know what that boost is going to be, that's when you determine what price you are willing to pay for that net gain. 

Now, what is it that a team in the West can sell? As I mentioned earlier, anything that is not scoring points right now can be sold. The biggest and most desirable of these is going to be draft picks. That is your liquid capital. It is, as I described it last week, the currency of dynasty. It's the currency of the realm. It is the most coveted asset by rebuilding teams, and that's important because rebuilding teams are the likeliest source of your boosts. Why would another contending team want to help you out? They wouldn't. A rebuilding team who is out of the playoff picture is going to be your likeliest source for boosts. They want draft picks.

Another thing you can sell that also may be desirable to rebuilding teams is what I like to call Broken Toys. These are your previously productive but currently injured players that generate no points for you when you need them the most. So these are people on season-long IR. They may even be just on temporarily, but you may wonder if they're going to be back for the playoffs that there are players that aren't helping you right now.

A rebuilding team can get their full gain of net production in the future by trading you a player who is providing points now for one they might expect to provide more points later. The point for you is you need points now. Having an injured starter on your roster doesn't do that, so that makes them an option for trading them to a rebuilding team. And it’s especially appealing for rebuilding teams who are looking to get younger. If your broken toy is younger and their productive veteran is older, giving that to you in exchange for the younger asset who will perform later is an appealing way for a rebuilding team to get better.

In the same way, developing talent, which are prospects and taxi squad players who aren't producing for you now, but could produce in the future, are pieces a rebuilding team could build around is something they might desire. 

A little farther down on the priority list is what I would call benched starters and next man ups. These would be the players who are directly displaced by the new additions that you're bringing onto the team. They might actually represent an improvement for a rebuilding team that they can use as starters, and then ultimately to put them as their depth pie pieces because they probably are lacking depth on their bench. These though are probably not going to get you anything in terms of a boost by themselves. They're going to have to be part of a package that includes any of the previously mentioned assets, most likely draft picks.

And then, finally, you have positional surplus. These are players that wouldn't crack your lineup in the fantasy playoffs unless a catastrophe struck, but these could become starters or depth pieces on rebuilding teams. So they might be part of a package as well to get you some of these boosts that you're looking for.

So now that we know what we can sell, what is it that we can buy? Well, the number one thing we want to buy if we are a win-now team in the West is points. We want a proven track record of performance with an expectation that that performance is going to continue. There is, of course, no guarantee to this. You might spend a couple of draft picks and bring in an aging veteran player who immediately gets injured and is out for the rest of the season. That happens. That's unfortunate, but, but there is no guarantee in fantasy football. 

But because your time horizon ends with this season's fantasy playoffs, it doesn't matter if this player you're acquiring won't continue this level of performance in the future. If we are looking at a player who is up against an age cliff, who is up against retirement, or whose performance has been declining over some time, we need them to deliver now. If they can't deliver next year, that's okay because we are concerned with this season only. 

That's the big distinguisher between Western teams and Northern teams in our compass metaphor. The teams in the North do care about next year. They're trying to contend perennially. The teams in the West are not as interested in that. They are trying to win this season right now. So any player who's putting up sufficient fantasy points on a regular basis is a potential purchase or a rental. 

Now what I call a rental, this is a term I pick up from the NHL trade deadline where teams will acquire a player who's a free agent at the end of the season. They know they're only getting them for their playoff push and they're gone. In the fantasy football world, a rental is someone for whom this may very well be the last year of starter-level production or the last year of their career. They're going to be worth nothing at the end of this season.

The biggest problem that you're going to face as a win-now contender trying to buy boosts off of rebuilding teams is that the pool of such players and teams is going to be very small. There are very few sellers, perhaps only one, maybe two. So most of the player pool that you could buy points from is not even realistic. Other contending teams don't want to make you stronger. Worse, other contending teams want to make themselves stronger, which means they may be targeting the same players on the same rebuilding teams that you are. So there's not much supply and there's multiple buyers which creates demand. And as we know, scarcity means expensive.

So what is that boost going to cost you? In the last episode, I said that there was a dirty secret about draft picks: that they have no inherent value whatsoever. What they are worth instead is whatever someone else will pay for them. And it turns out boosts are also in that same world. They have no inherent value, but they are worth whatever a contender is willing to pay for them.

So I want to give you kind of a high level, very oversimplified, general conversion chart that is agnostic to whatever may be going on on your team in your league. Your results may vary, but a high first-round pick should be able to net you a cornerstone or perhaps two starters. You are looking for at least a full Starter Booth if you're going to trade away a high first-round pick.

The problem is, of course, that you probably don't have one of these unless you acquired it in a past trade. Your own first round pick is going to be late round. Hopefully the 1.12 or whatever the last pick in your round is because you're going to win a championship. A late first-round pick of course is not worth what an early one is in the eyes of most managers, particularly rebuilders.

So if it's a late first that we're talking about, you're hopefully getting a starter, most likely a productive veteran plus some veteran bench depth, but probably not a full Starter Boost for this by itself. You may need to package that late first with some other assets. 

When you get to a second round pick, by itself, you're looking at getting a lower end starter or a rental, probably in the neighborhood of a half Starter Boost or a little less than that. And with a third-round pick, you shouldn't be expecting much of anything by itself. At best, a quarter Starter Boost, but most likely that's going to be a Bench Boost by itself.

But these guidelines may not be good enough in terms of what you're going to have to pay. You have got to deal with market frictions that there are very few sellers and potentially multiple buyers. The rebuilds have all the leverage here because they have the thing that you need now. The thing they need, they need later, so they have the power now to negotiate with you and any other contenders to extract the most value that they can. 

They also possess the certainty in this equation because, as we've noted before, players who are performing and have a track record of performance tend to continue to perform. That's the certainty aspect of it. You're buying a certain amount of points for this transaction and we know that certainty costs a premium. You're paying that premium for certainty, but that's okay if it buys you a championship.

One of the ways to reduce market friction is to act early. This is possible if you've made West your strategic direction early enough in the season. It's a little harder if West is a course correction for you. If you buy early, you can beat the 6-2 late buyers who are just coming into the realization that they could win a championship this year. 

You might also be able, the earlier that you make these kinds of decisions to buy boosts, you might be able to exploit what I would call an injured star discount. These are players who are out during the regular season, but plan to return in time for the fantasy playoffs. So they're gonna miss a chunk of time, but they're going to be fully healthy later. When you buy them at the time, they may be doing nothing for your lineup, but they'll provide that boost at the end of the season because it is much more important to have more points in Week 15 than it is in Week 6.

But this is a kind of selective aggression about when to push your chips in and when to spend draft capital and developing talents and youth on your roster. There can come a point where you really don't want to do that. Even if you are in win-now mode, there are times when you should pull back. Just because you're willing to shove all your chips into the pot doesn't mean you should shove all of your chips into the pot.

This is especially true when we are looking out into the future. The farther out you mortgage your future by trading high draft picks in later years, the harder your fall is going to be and the longer your rebuild is going to take. Now I've said if we are in win-now mode, that's all we are concerned about is winning now, but this is the price of throwing everything you have at winning a championship this year. You may be in for fall and it may take a while to get out of it.

Now, one of the easiest ways to fall into this trap is having to pay too much for too little. Let's say that you have in your wallet a $100 bill and a $20 bill, and no way to make change with that. You have one or the other. The person you're trying to buy something from is selling that something for $50, and they are unwilling to make change. So if you want to buy that, you either spend the $100 and lose an extra $50 in that process, or all you have is $20 and you can't buy it. 

That's kind of where this having to pay too much for too little comes into play. There is a inherent drive in us when we are trying to pursue a championship now to pay whatever that costs, even if it means paying, in this case, double what it's worth with no ability to get anything back. If you do that, you hopefully will get that championship, but it's gonna cost you a lot more down the stretch.

So if you've reached a point where you want to pull back that all-in bet, there really are two strategic paths you can take in our compass metaphor. Those are North and East.

North you go to become a sustained contender. If you have a strong roster and you have some draft picks, then you can reload after this season as a choice instead of trying to boost this season. Now, if you are already in the North and you are making a pitch to win now, then it's a fairly easy pivot to go back to just relying on your strong roster to carry you for a few seasons, and then reload as you go. So instead of selling broken toys and developing talents, you would actually try to trade for them. You stay good  now, you get great later.

The other strategic direction you can go is East, which is a safe harbor kind of approach. Now I've called East the land of a chip in a chair, which is a poker metaphor that you can win any poker tournament as long as you still have a chip and a chair at the table. In this particular case, you've got a whole lot of chips when you get to the table. So if you are to a point where you need to pull back from your all in bet, stand pat and make only small logical moves that keep you in a playoff position and keep your options open for future seasons.

And you never know. This might be your year after all. I know I have won a number of dynasty and other fantasy football championships coming out of the sixth seed as a playoff qualifier on the last week of the regular season. So it can happen. Once you get into the tournament, things can happen and maybe you can do that without getting a boost at all, but you pull back from win now at all costs to, let's see if I can win.

Now, that could be hard to do. But if you recognize that you're going to have to mortgage too much to get too little back in your attempt to win right now, then going the safe harbor route into what I call the East is a smart way of managing that tension and still give yourself a shot at winning. 

So we are nearing the trade deadline in most fantasy leagues. Now, hopefully you're in a dynasty league that doesn't have a trade deadline, giving you more flexibility to move assets throughout the season. Most leagues do have one, and it's coming up pretty fast. We've talked about what the win-now teams in the West need to do toward a trade deadline.

Next week I'm going to talk about the other three directions and how they need to approach this deadline. So thank you so much for listening, for watching, for liking, for subscribing. Please, please consider writing a positive review about this podcast. Apple and YouTube are the most helpful places that you could do that for me. I would really, really appreciate that. 

Please consider sharing on social media, and please subscribe and like, and stay tuned. Next week, I will be back and we will have another episode of Dynasty Compass talking about the trade deadline. Until then, go win your week. Go win your league.