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There's a lot of really strong dynasty analysis out there, especially when compared to five or ten years ago. But most of it is so dang practical-- Player X is undervalued, Player Y's workload is troubling, the market at this position is irrational, and take this specific action to win your league. Dynasty, in Theory is meant as a corrective, offering insights and takeaways into the strategic and structural nature of the game that might not lead to an immediate benefit but which should help us become better players over time.

If You Want To Win, Stop Trying To Win

Two weeks ago, I wrote about how complicated models tend to outperform simple heuristics (or rules of thumb) in environments with low uncertainty, but as uncertainty increases, that observation tends to flip. Last week I gave two such heuristics that perform well in rookie drafts. This week, I have a related rule of thumb that has served me well in the day-to-day management of my dynasty team.

A good heuristic should be like a slogan— it may convey a complex concept, but it should be easy to say and easy to remember. As a rule of thumb (and yes, I have heuristics for how I create heuristics), I like to say that if I can't convey an idea in ten words or less, it probably needs a bit more time and testing in the lab.

So here's today's slogan: "Chase value, not wins".

For most of us, winning is the whole point of fantasy football. To borrow a quote from former head coach Herm Edwards:

This is what's great about (fantasy) sports. This is what the greatest thing about (fantasy) sports is: you play to win the game. Hello? You play to win the game. You don't play it to just play it. That's the great thing about (fantasy) sports: you play to win, and I don't care if you don't have any wins. You go play to win. When you start tellin' me it doesn't matter, then retire. Get out! 'Cause it matters.

Edwards' issued that rant after his Jets fell to 2-5 on the season. They went on to win seven of their last nine games, secure the AFC East divisional title, and thrash the Indianapolis Colts 41-0 in the wildcard round before losing to the Oakland Raiders. His Jets embodied his speech; they played to win the game.

And that's good. I think winning the game is a laudable goal, and I'm not here to say it shouldn't matter to you. If you start telling me it doesn't matter, then quit. Get out! Because it matters.

But there's a big difference between us and Herm Edwards and the 2002 Jets. NFL coaches and players have a direct impact on the outcome of the game. They can immediately improve their chances of winning even in the middle of a game just by personally doing their job better.

But our closest parallel in football is not to the head coach but the general manager (which is why we're often called "fantasy football managers" but rarely called "fantasy football coaches"). We assemble the team to the best of our abilities, and if we do our job better than our competitors, we'll be more likely to win than they are. But once the game kicks off, we lose all direct control over the outcome.

I like to contrast Edwards' tirade against another famous (and colorful) rant, this time by Billy Beane, a general manager.

My s*** doesn't work in the playoffs. My job is to get us to the playoffs. What happens after that is f****** luck.

Several years later, he expanded on it in an interview:

Bleszinski: You famously said, "My s*** doesn’t work in the playoffs." Do you think that’s still an accurate statement?

Beane: By and large, out of 162 games, the best eight teams will get to the playoffs. Cinderellas in May aren’t there at the end of the year. I said eight, but it’s 10 now. You have the 10 best teams because you’ve gone through the season. You get into a short series, anything can happen. There’s no accounting for random events that happen. There’s nothing that you can plan for in order to prepare for those random events. Over a season, they get washed out, but in a short series, they don’t. The last two World Series Champions, one made it the last day of the season, one made it the second to last day of the season. They were very good teams, but I don’t think their business plan was to barely make it to the playoffs and then win the World Series.

…

Bleszinski: Is the team going to have to get over that hump and win the World Series in order to fully validate the A’s process, or is getting in the playoffs with that budget enough of a success?

Beane: I don’t think about validation. You always want to win the championship.

Bleszinski: All you can control is being that team that succeeds over 162 games.

Beane: Yeah, exactly. You just put yourself into that tournament enough times and…

Bleszinski: Eventually, you’ll win it.

The added emphasis is my own. Beane agrees with Edwards: you always want to win the championship. But he doesn't have any direct control over the day-to-day business of winning games, so he places a lot more emphasis on the role of luck, prioritizing good processes and trusting they'll eventually lead to good results.

Both have "winning the game" as their ultimate goal, but for Edwards, it's also a proximate goal— the thing he is directly focusing his energy on. Beane treats "build the best team possible" as his proximate goal and winning games as downstream from that.

With this in mind, I want to talk about "win-now" trades in Dynasty.

Winning Is Good, Actually

Again, I want to win. If I have a good team right now, I fervently hope it can live up to its potential and bring home a title. Despite this, I am strongly against making "win-now trades". But why? Is it so wrong to want to make moves to increase the chance that happens?

Of course, it's not. My goal is to build the best team possible, but there's nothing that says "putting more points in your lineup today" can't make my team better. (Points, like winning, are good, actually). If I have a team with title aspirations and I can increase the points it is scoring as well as its total overall value, that's a slam-dunk move.

For instance, if a team that is out of contention offers my competing team Travis Kelce for Dalton Kincaid, I'd be foolish not to accept because I think Travis Kelce's total value is greater than Dalton Kincaid's. (Let me rephrase: I think Kelce's value in years I care about is greater than Kincaid's. But I get why a struggling team might feel differently; they don't care about this year anymore— in fact, they'd probably rather perform poorly in 2023 to secure a higher draft pick— and it seems very plausible that Kincaid will offer more value than Kelce in 2024 and beyond given that Kelce will be turning 35.)

I don't consider this a "win-now" trade; I consider this a "maximize value" trade (that also happens to make me better in the short term). And when it comes to "maximize value" trades, you can consider me Sam-I-Am. I will make them in a box, I will make them with a fox, I will trade for someone old, I will trade with someone bold.

"Win-now" trades are a different category entirely; they're trades where you are receiving less total value than you're giving up, but you're making that sacrifice to increase your chances in some narrow window. These directly contradict the "build the best team possible" ethos, and while good publicity has them known as "win now", they'd be just as accurately described as "lose later".

Here's the rub: while I completely understand the instinct to maximize a competitive window, the reality is the teams that are in a competitive window are likely the ones that best avoided these types of trades in the past. They went about the slow and unsexy business of improving their roster piece by piece until it stood above the competition.