Onward—always onward—the calendar tacitly mandates. Auctions and drafts are now the past. Closing in on us is the in-season trade market.

Most of the leagues in which I participate do not see heavy trade activity at this point of the season. The adjective “heavy” in this instance (when affected by the preceding “not”) describes both the volume of trades (minimal) and the magnitude of trades (minor). But, once every so often, maybe once a season, maybe even less frequently, a big trade gets made. If we expand our requirements to include the entire season, not just the beginnings of the trade season, then we will still usually only find a few big trades.

We have often discussed the virtues of hustle as it relates to trades—that through hustle we can make more, often small, trades that can slightly improve our odds of winning and, even better, that we can do so while our risk-averse competition often chooses to avoid reaping the benefits of this strategy. The hustle and the small trades that ensue are great, and while these types of trades are often readily available, there is a more elusive, yet still wholly valuable and worth our efforts, type of trade out there: the big trade.

The big trade is our white whale. Most seek to avoid the danger, but the reward makes it worth the risk. Sometimes the winning team has the best team from the onset and only needs a few small trades or keen free agent pickups in order to capture a title. Often, though, and particularly in keeper leagues, the winning team completes a trade in-season that significantly improves their team. I say this to note that our quest to make such trades is a quest worth undertaking. Effort alone, though, will not be enough to succeed. We are going to need a plan and we are going to need strategies if we are going to make difference-making trades this year. As we so often do, we first need to examine the obstacles we are up against if we are to conquer them in our pursuit of these trades.

The Obstacles

Our obstacles faced in making big trades are familiar ones to the pages of The Quinton; they are (per my estimation) loss aversion, league norms, and defensive decision-making. These obstacles are not entirely independent of each other and thus we will discuss them together.

Even if a big trade (for our purposes we will define a “big trade” as a trade in which one or both teams exchange multiple impact players or assets (with an “impact player or asset” being a player or asset that has top-75 expected value for either the short term or long term)) makes sense for both parties, many fantasy baseball participants will refuse to partake because we (humans) are more motivated to avoid losses than seek gains. This is straightforward loss aversion, but it also brings our other two other obstacles into play. Obviously, it is more defensible to hold onto such assets than to make a splash and potentially get burned. Add in that most leagues bemoan such trades (with such backlash often including the ridicule of other owners) and we can see why most avoid big trades. That said, as mentioned earlier, big trades do happen. Given this, how can we be the ones to benefit from them?

The (Potential) Solutions

The Untouchables

The first component of a big trade is usually a player that most thought to be untradeable. In the latest episode of the There Is No Offseason podcast, Ben, Bret, and Craig (listed both alphabetically by first name and by assumed residence from north to south), discussed a trade in which a team would acquire Carlos Correa, Chris Sale, and Corey Dickerson for Bryce Harper and two other players (I forget the other two, but I am pretty sure one was Chris Colabello). This definitely qualifies as a big trade, but the only way you get in the door is by entertaining the idea of trading away the very thing you least want to trade, in this case, Bryce Harper. Obviously, this gets the point across, but it does not have to be this drastic. In leagues where the norm is to never trade exceptional keepers, trading away a rookie eligible Addison Russell or a 2015 mid-season Joc Pederson (an extremely valuable keeper that we had never seen fail), could be all that is needed to grab a substantial reward. The easiest thing to say in trade talks is “I am not interested in moving Player X” and move on to something else. However, if we are willing to entertain moving such a player, the reward might be even greater.


But even when we are willing to move such a player or if there is no such player to trade, even if we are willing to dance, we still need to find a trade partner. Occasionally, I would even venture to say rarely, such a trade partner finds us without the need for seeking or persuasion. For all those other times, though, we need some way to get our potential trade partners to put aside the aforementioned obstacles to a big trade. The intuitive answer is to provide a logical argument as to why someone should trade us a bunch of really valuable stuff. The problem with this is two-fold. First, we are trying to get others to overcome loss aversion, defensive decision, and league norms, which are not predicated on logic to begin with. Put differently, millions of people regularly play the lottery knowing that it is not a profitable bet. Secondly, no matter how intuitive it seems at first, “providing a logical argument as to why someone should trade us a bunch of really valuable stuff” on second read seems wholly illogical. People do not want to give up stuff. They especially do not want to give up stuff when someone tells them it is in their best interest. We (humans) just do not roll like that.

Think of all the extraordinary things you have ever done or tried to do. More than likely, you did not decide to do so after reading a list of facts or hearing a perfectly logical argument. Instead, it is likely that you heard a story and then imagined a future. This is why books and music, and more specifically, stories are so powerful, not just in how they are able to make us feel, but also to how they are able to make us act. In A Whole New Mind, Daniel Pink writes, “Most of our experience, our knowledge and our thinking is organized as stories.” If we are going to try and fight the way our mind is naturally wired (such as risk aversion), we will likely have more success hacking the program using its native tongue.

Do those agreeing to such trades do so to mess with the rest of the league or because they are bad at fantasy baseball? Probably not. Instead, it is likely that they heard a story and then imagined a future. This then becomes the fine line we must walk in order to get others to agree to trades with us. We must tell them a story about how a trade will drastically improve their team (either for right now or for the future) without patronizing them, without setting off their B.S. meters. In other words, just as we put in so much effort to follow all the games and players and to know all the facts, we also must put in the time to be better storytellers. In trade talks (and in most of life) the 99 percent of stories are short and sweet and do not even feel like stories. They sound like, “Players X, Y, and Z will set you up real nicely for next year and the following years in both steals and homers. I’m interest players A and B for this year to make a run right now. It’s like the trade Owner Z made to win a few years ago.” Or they sound better. They barely sound like stories, but they certainly do not sound like analysis.

I used to be a really bad storyteller. Now, if I get lucky, I can tell an above-average story. And the only way I have ever gotten better at it is observation, practice, and reflection. So I’d advise we all do actively work on our storytelling. The most helpful thing for me, though, was learning that telling a story in such a situation, can often prove to be more effective than a logical argument. So get out there, get seeking those big trades, start entertaining the idea of trading the untradeable, and start telling stories instead of telling people what they should think.

Thank you for reading

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I find that the problem I have trading players is that the reason I have these players is I like them better than other people in the league like them. So at the go I am looking at trading a player the other guy isn't that hot on for one that I am lukewarm about, but might be a better fit at the moment.

It is easier if players have shifted significantly in value over the course of the season leading to an imbalance. If I have a guy who worked out really well on the bench, a trade makes sense. But it is hard to establish that in the first month of the season so that kind of trade is not really a season-starting kind of trade.