I don’t have anything to say specifically regarding third base, so I wanted to use this week’s article to discuss a subject we have not yet touched this year in this column: pre-draft and pre-auction trades in keeper leagues.

In theory, we should see two types of trades: the at-different-points-of-the-contention-cycle trade and the challenge trade. The first happens when teams value players differently because of their difference in distance from competing for a championship. A team, for example, competing for a championship this year might find great value in Victor Martinez, whereas a team that will not be competing for a championship the next two years will have no value for Martinez other than what he can return via trade. Meanwhile, a challenge trade happens when two teams just value players differently. Because of our old friends the endowment effect and defensive decision-making, these trades rarely happen.

There is another, less theoretically obvious trade type that we see in keeper leagues that can lead us to suboptimal decision-making, which, as always, we hope to both avoid ourselves and take advantage of when our leaguemates fail to avoid doing so. This trade type is the roster construction trade. This is not trading away a one of your four keeper first basemen when you can only keep three. We’ll call that type of trade a roster constraint trade. Rather, the roster construction trade is when we have three closers as keepers and we trade one for a shortstop because we think we need a shortstop more than we need a third closer. We see questions about these types of trades all the time on the Bat Signal—“I have two top five third basemen, should I trade one for a top ten second baseman and borderline keeper of a starting pitcher?” While these trades can certainly be optimal, they very often are not.

Why is the roster construction trade often suboptimal for the team trading from depth? It is often suboptimal because it often leads us to trade better keepers for worse keepers. We make this mistake for several reasons. One reason we do so is that we overrate having options. We discussed why we do so at length in the previously linked article, but the most pertinent section from the article is as follows,

“In Predictably Irrational, Dan Ariely shares his findings that people fear losing options and will go at great, often counterproductive length, to keep options open. In testing this through experiment, Ariely concludes, “[the participants] just couldn’t tolerate the idea of [losing an option], and so they did whatever was necessary to prevent their doors from closing.”… The problem is that by doing this, we are usually overvaluing a small probability.”

Often, when we make these trades, we think we are freeing up our chances of getting a great value on that one player who falls in a draft or goes way too cheaply in an auction. The issue with this is that the pang felt when imagining missing this opportunity does not elicit a correctly proportional response to the actual odds of being able to capitalize on such an opportunity. For starters, we often do not know at which position the best values are going to be and when such opportunities are obvious, they are often also obvious to our competition, which means such expected opportunities will likely be reflected in the trade market as well as in league-wide draft/auction strategies (thus making them, again, less valuable than we often think they are).

The next and maybe biggest reason we agree to trade better keepers for lesser keepers is that we think we know what a winning team looks like or does not look like. We say things like “the winning team usually leads in home runs” or “a team has never won punting an entire category.” We then use those things we say or think to inform our decision making when it comes to deciding which players to keep, which players we would like to trade, and which players we would like to trade for. We hear this all the time in sports analysis—that something will not work because it has not worked before, that in order to succeed teams need to have certain characteristics. This is likely a result of risk aversion and a phenomenon Daniel Kahneman calls, “What You See is All There Is.” If, for example, we cannot imagine a team that keeps three second basemen (let’s say one in the 2B slot, one in middle infield slot, and one in the utility infield slot), then it is likely that we will be willing to trade a one of those second basemen for an inferior keeper. Sticking with this example, if we can get an equally valuable keeper at another position for one of our second basemen, then we should by all means be making such a trade as there is value in having our utility slot open; that said, we need to make sure are not overrating the value of that option nor overrating a type of team construct.

I try not to use personal experience too often because anecdotes are usually unhelpful and often detrimental. However, I will use one here in order to show that an irregular combination of keepers can win. Over the last handful of years in my NL-only and AL-only keeper leagues, we have seen teams win in very different ways, with very different keepers. Winning teams have entered the auction keeping five outfielders, without keeping a catcher, keeping two second basemen and a DH, keeping no relievers with only two closers available in the auction (thus punting saves), keeping the full 15 keepers, keeping as few as 10 keepers, going into the auction with a lot of money available, and going into the auction with the fewest dollars to spend (both in total and per player). These teams often won because they had the best keepers and thus gave themselves the best odds of having the best post-auction roster, which in turn gave them the best odds of winning. (Also, I can speak to the intent for some of those teams as some of these teams were mine (yes, this disclosure is also a brag)).

Most importantly, this anecdote brings us to how we should take advantage of our leaguemates’ and our tendencies to try to collect keepers that keep our draft and auction options open, while assembling rosters that “look” like winning rosters (which really means they look like previously victorious rosters). The reason these collections of winning keepers often looked so strange is that (i) these owners did not trade players that seemed redundant for inferior players for the sake of keeping options open and (ii) these owners were often the ones trading for the superior keepers being traded for these arbitrary reasons. We know that being less picky about roster construction allows us to get the best values in drafts and auction and it seems this is also the case in the offseason trade market.

As always, just as we want to avoid decision-making traps, we want to be the ones there to take advantage of such traps when our leaguemates fail to avoid them. In this instance, we should first search our leaguemates’ rosters for instances of faux-redundancy to see if they are willing to trade value for flexibility. We should also take a look at what has worked in the past for our potential trade partners and what has not. From there, we should see if we can get favorable trade terms by allowing them to pursue the former and/or avoid the latter. If we are not the one taking advantage of such tendencies, then it will likely be one of our competitors doing so; thus, as always, hustle is rewarded. With keeper league pre-auction and pre-draft season either upon us or coming upon us shortly, let us therefore make sure that we do our homework in order to give ourselves the best odds we can.

Ariely, Dan. Predictably Irrational: The Hidden Forces That Shape Our Decisions. New York: Harper Perennial, 2010. Print.

Kahneman, Daniel. Thinking, Fast and Slow. New York: Farrar, Straus and Giroux, 2011. Print.

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Very timely article, thank you. I am currently in a 10 team league, with 10 keepers. I have Carlos Correa, Xander Bogaerts, and Trea Turner, (and Machado) and was thinking "Do I really need three SS/2B keepers?". I finished in 3rd last year and am ready to "contend now". I may make a deal, but I'll certainly do it in a much better position thanks to this analysis.