The Art of Dynasty | Chapter 13 (Trade Assessment)

Building a dynasty fantasy football team requires strategic thinking and football acumen similar to planning a long military campaign. You must intimately understand your leaguemates’ rosters and tendencies, diligently prepare for the rookie draft and waiver wire, and thoughtfully craft a balanced yet versatile roster aligned to your vision. Knowing when to push all chips to the table for a title run or temporarily rebuild for sustained excellence is equally critical. The finest dynasty owners combine sharp situational analysis with statistical rigor and old-fashioned football study to construct juggernauts that dominate their leagues for years.

This guide outlines core tenets to help you architect a formidable roster poised for both immediate and enduring success. By internalizing essential dynasty strategies around planning, preparation, roster construction, and pivoting between competing goals, you too can rule over your leaguemates year after year like a battle-tested emperor of old.

    1. Startup Drafts
    2. Roster Construction
    3. Ideal Archetypes
    4. Ship Chasing
    5. Iron Bank
    6. Rookie Pick Values
    7. Rookie Drafts
    8. Trading
    9. Roster Management
    10. Bayesian Inference
    11. Startup Supreme
    12. Roster Crunch
    13. Trade Assessment
    14. Productive Struggle
    15. Game Theory
    16. Startup Trades & Pick Swaps
    17. Winning the Offseason
    18. Rebuild Roadmap

Early on in my fantasy football life, I blindly followed a couple of dynasty analysts that I respected. A player that they had suggested to buy absolutely tanked and it really bothered me because I had chosen to blindly follow their advice without doing my own due diligence. In the end, I had no right to be upset because it was ultimately my decision and responsibility — only I was to blame. With that said, I learned two invaluable lessons:

1. Someone else’s opinion (regardless of how smart they are or how many followers they have) was only a part of a decision tree.

2. It takes a lot more discipline, time, and effort to make your own plan when building a dynasty roster. This is also scarier because it means that you are ultimately accountable for both your good and bad decisions.

So how do you make sure that you are constantly improving where it matters most in dynasty fantasy football? Trading is the lifeline of a dynasty team and if you are not actively working to understand your own tendencies as well as your opponents’ then you are destined to fail. I suggest keeping a trade journal where you note the reasons and thought process for executing the trade, your leaguemates’ habits, and details of the trade itself.

Consider these 3 steps to assess a trade and use this in your process:

Fundamental Analysis

Considering the fit of a player or asset with your team’s needs. Are you in win-now mode? Then you need to add players who will produce immediately. If you are in a rebuild then it is about stockpiling picks.

Too many people in rebuild mode want to maximize every asset but it generally doesn’t work like that because there is no leverage. Get what you can and move forward. Leverage is gained over a series of moves and at opportune moments. There’s no instant rebuild button.

Technical Analysis

Assessment of a player in relation to archetypes (or what Jax calls “Anatomy”) to determine the level of success and/or risk that a player carries. This portion is about managing risk to your dynasty roster and moving off aging players or those who have exceeded expectations and likely will not return consistent production going forward.

Market Sentiment

Never overvalue the results of a trade calculator in the present. As we often see, what may seem like a win (or loss) today can quickly change overnight. I often say that situations change faster than talent and trades are not immune to this reality. I will use a trade calculator whether it’s Dynasty Dominator, Dynasty Trade Calculator, or even Keep Trade Cut (which I despise) to my advantage. This doesn’t mean taking screenshots to show your opponent that the deal favors them but I will check what the market is saying about a specific player or deal and try to identify market inefficiencies.

The market and these calculators are slow to react and they fall prey to bad analytics or overhyped public perception. And where possible, try to juice as much value out of a deal as possible (not to be mistaken with being greedy and losing the deal altogether). Over the years, I have developed a reputation for maximizing value at every turn, what my leaguemates call the #ChalkSqueeze.

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Chalk
Chalkhttp://theundroppables.com
The ringleader of The Undroppables, Chalk works in the shadows and behind the scenes of the brand. With a preference to remain a supporter and facilitator of the team’s influencers and personalities, Chalk’s focus is to ensure that The Machine stays well-oiled. With years of experience across dozens of leagues, Chalk brings deep and actionable insight to his fantasy football analysis. You can follow him on Twitter at @101chalk.

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