Over here at The Quinton we are interested in finding little things that can make a big difference when participating in fantasy baseball. We are equally interested in finding out how we can capitalize on these findings. Put differently, when our competition does not properly value a particular player, type of player, type of production, or strategy, we want to be able to take advantage.

Because we often cannot tell ahead of time what our leaguemates will improperly value, we preach the importance of strategic agility—the ability to change course in order to take advantage of dynamic conditions. It sounds good and hip, but just saying “be strategically agile” is not very helpful. In order to be more strategically agile, we will today take a look at some of the obstacles to strategic agility.

(Note: while this applies to keeper and dynasty leagues for the offseason and drafts/auctions, it will still apply to re-draft leagues, just not until the drafts/auctions.)


Come the end of the season we have either stayed the course with our preseason strategy (win/rebuild/ramp-up to winning/etc.) or pivoted midyear. Either way, though, we did not enter the offseason with a blank slate. As a result, we had some idea of what we planned to accomplish come the offseason. For example, after clearing out our minor leagues while making a run at a title, we knew that we would probably be trying to restock during the offseason.

This is well and good, but it can be hindrance. Sometimes people say perception is reality. For our purposes, we should note that having an idea of how the future will or should unfold, makes us less likely to see deviations to those assumptions or forecasts. Moreover, it makes us even less likely to be able to capitalize on these unforeseen opportunities as they arise. If we assume that closers are going to be too expensive to acquire or that certain minor league draft picks won’t be available via trade, then we are likely to miss out should our assumptions prove wrong.

The key here is not to be without strategies and assumptions; rather, the key is to know what our strategies and assumptions are in order to know how they might be limiting us. This is where it pays to listen. Instead of only telling other owners, “I’m interested in trading X for Y,” if we can occasionally have broader, more strategy-centric conversations, then we will more often find what our assumptions missed. This is no easy task and many owners are not interested in such discussions, but given the upside (and the advantage it provides over the owners who do not partake in this practice), this is certainly worthy of our efforts. And that brings us to our next obstacle.


Being strategically agile may sound like a low effort strategy in that there is no need to develop a plan, that instead, we just sit back and take what the market is giving us. Unfortunately, “be easy” does not alone make us strategically agile—well, at least not effectively strategically agile. To best be able to pivot we actually have to be more prepared than those who will be executing a pre-planned strategy regardless of competitive response. Whereas the strategically inflexible need prepare for the single strategy they choose to employ, having the confidence and capacity to shift gears mid-offseason or mid-draft often requires being prepared for multiple scenarios.

We quickly reject certain ideas: trading away the top minor-league draft pick, trading for a great bat that will have to be put in the utility slot, trading away our only decent starting pitcher, and the like. Many of the inquiries into these valued players and resources are no good and worthy of immediate dismissal. When we combine this half-baked analysis with a healthy dose of unhelpful trade offers, we get conditions that lend themselves to missing unexpected opportunities.

We have discussed this before, but it is important to note that our goal is to make moves and employ strategies that help our team the most. This is a complex goal and our shortcut creating minds make shortcuts to help us accomplish this goal. The key is to make sure, come trade offers and strategy planning sessions, that we do not let these shortcuts stand in the way of proper analysis, even if it does require some extra effort.


Lastly, even if we have no problem putting in the effort and effectively handling the previously mentioned momentum, the ambiguity effect—a cognitive bias that shows our preference for more certain odds to less certain odd—can still steer us toward pre-planned strategies. Building strategic agility into our process involves a certain amount of uncertainty. While we recommend planning for multiple scenarios, we cannot plan for every scenario. Being strategically agile, therefore, gives us less certain, albeit most likely better, odds. We can therefore see the temptation of making off-season strategic decisions such as “there’s no way I’m trading away my only closer with none available on the market” or “I just can’t start to fully go for it with so many good teams in the race.”

Again, shying away from ambiguity might make us feel more confident in our strategy, but it will not give us a better strategy. As mentioned when we looked at the ambiguity effect’s effect on player valuation, we need to be able to analyze our own process. In order to find the areas in which we are shying away from ambiguity, we have to go looking (with the ambiguity effect in mind). More often than not, the ambiguity effect will show up when we analyze our past decisions, usually at the trades we did not make or the strategy employed by others that we did not consider.

As boring (or interesting) as it is, this always seems to come back to analyzing our own process and assumptions, to critically thinking about how our opponents and we think. So let us keep building in that additional layer of analysis into our process, and hopefully we will be that much more strategically agile this offseason.

Thank you for reading

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