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In most fantasy baseball leagues, it is officially trade season. Early-season fluctuations have showed themselves as such, injuries and call-ups have re-arranged the talent pool, and most leagues’ competitive landscapes have come into focus. As we have discussed many a time, making a trade is far from making an offer to a leaguemate that makes sense for their team. Furthermore, making a trade is not even making an offer to a leaguemate that makes the most sense for their team. Hence, a reasonable question to ask at this point is, “well, then what matters to be successful in making productive trades?”

The answer is that a lot of things matter. We have looked at trades from all different angles, from markets to effort to league norms to negotiation styles. We have looked at trades at the broad, strategic level and we have looked at the granular, actionable level. All that said, and given the time of the year, I thought it would be helpful to put all of these important principles in one place. While I will not touch on any subject in depth, I will link to articles where you can find a more in-depth look at the particular subject.

Quantity Matters

There is a belief that because trades can be very impactful that we need to get every trade right. The problem with this notion is that the only way to make sure we do not get a trade wrong is to not trade at all. Less melodramatically, even if we only accept the slam-dunks, we are going to be leaving opportunities to upgrade our team on the table—and we will be doing so only to avoid making a mistake. The crazy parts are (i) that this does not seem crazy to our risk-averse wired brains and (ii) that we think we can know the future with such certainty. Additionally, the way trades often work is that if it is not one team (read: your team) benefitting from making a trade for a player that is available, it is another team (read: your competition) doing so. All this is to say that our goal should not only be to avoid making bad trades, but it should also be to make as many beneficial trades as possible.

A couple of caveats before we move to the next point. The first caveat is that trades are not independent of each other in that making a trade might preclude us from making a better trade, but more on this in the Timing Matters section. The second caveat is that while we should be searching for as many helpful trades as possible, we do not want to force a trade to match a theorized outcome, we do not want to put the cart before the horse, and we do not want to make unhelpful trades just because of something written on the internet (so look for trade opportunities, but do not force them).

Effort Matters

While the first key to making more trades is properly framing our strategy (as discussed above), the next key is effort (trying to make trades and engaging in trade talk). As we have mentioned before, we probably overrate winning trades and underrate simply making productive trades. While having more lines in the water will lead to catching more fish (responsibly, humanely, and figuratively), there are other advantage to engaging in early season trade talk. The previous link is to the full article, but the quick version is that early season trade talk allows us to potentially (i) use our leaguemates’ desire to appear logical against them (use something they said previously in trade talks to our advantage later in a negotiation), (ii) be top of mind for a leaguemate once they decide they want to trade for something, and (iii) ease the tension of more serious trade talk.

Research Matters

Engaging in productive trade talk, however, is not something we just get to choose to do. It is a skill, albeit a relatively easy one in which to be proficient. Blindly emailing or messaging leaguemates with “Any interest in Player X?” or “Looking for a closer” might work occasionally, but in order to improve our chances of getting to meaningful trade talk, we need to show an understanding of our trade partner’s needs. This is where the research comes into play. We need to not only to find out what the needs are of our leaguemates, we need to know their alternatives, their competitive situation, and their trade tendencies. Asking someone who never trades their prospects to part with the best prospect in the game will probably not get us anywhere. Asking if someone is interested in a steals-and-average shortstop when they already have a comfortable lead in both categories is probably not going to get us anywhere even if the player is an upgrade in a vacuum. The upfront research will allow us to avoid this unproductive talk and hopefully allow us to enter productive trade talk with more frequency.

Listening Matters

More important than the research might be listening to the responses we get from our leaguemates. No matter how rational or tendency-adjusted our research is, our leaguemates are going to have different ideas about their team needs and value players differently than we do. This is great because we want to trade players we value less to teams that value them more, so long as we are getting a proper return for them. We often miss these opportunities, though, because we are so locked into our own line of thinking and our own team needs. By simply listening to our leaguemates during trade talk, we are going to find trade angles that we did not even know existed (yes, this is another reason why effort and trade talk matter).

Timing Matters

While effort, research, and listening are great, knowing the best times to try to make trades can be a boon. In order to know this, we need to be able to assess the current trade market and predict future trade markets. Being able to assess how the trade market is going to move involves both an understanding of league norms and a forecast of how the competitive landscape (and therefore trade market) will change between now and the trade deadline. This is a very difficult task, but the better we are at predicting the future of the trade market, the better we can know when it is the optimal time to make a trade.

This is a situation where knowing ourselves as forecasters is important. If we know that we are not good forecasters or if the competitive landscape is particularly difficult to assess for a given league, then we should not get too cute with timing. In other words, the less accurate our forecasts, the less we should be weighing timing in our decisions. Alternatively, if we are good at forecasting the trade market for a particular league, we should be factoring future supply and demand into our trade strategy.

Negotiation Style Matters

Knowing our own negotiation style as well as the negotiation styles of our leaguemates is going to be invaluable. It allows us to know where we are most vulnerable (be it being overly cautious, overly accommodating, etc.), while also allowing us to figure out how to best negotiate with individual leaguemates.

Design Matters

Not only does negotiation style matter, how we structure our trade offers matters as well. By designing our behaviors with cognitive biases such as tyranny of choice, decoy effect, and compromise effect in mind, we can engage in productive trade talk more frequently and nudge our leaguemates toward certain desired (by us) choices.

You Matter

We can talk theory, strategy, and process all we want, but how we are perceived by our leaguemates might be the most important factor. If we take forever to get back to other owners, make outlandish offers, ridicule people for making offers we deem outlandish, or are unpleasant to negotiate with for any other reason, then we risk being avoided intentionally and unintentionally in trade talks. Conversely, being someone who people enjoy or feel comfortable dealing with can be the reason we are the first person that an owner reaches out to when wanting to trade. Being enjoyable to work/negotiate with might be a soft skill, but, regardless of categorization, it is definitely an important one.

Ultimately, using trade to our advantage in fantasy baseball is about a lot more than finding undervalued players. Just as finding these undervalued players is a part of our current trade process, all of the above skills and strategies should be, too. We will be more successful fantasy baseball participants for it.

Thank you for reading

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This all makes sense Jeff, but the problem I always have is other owners who either don't respond at all to requests or flat out reject a trade without any comment. Tough to get any dialogue going in either case. How do you counteract that?
Don't start with a trade offer. Send an email saying that you're looking to increase your steals (or whatever you need that the other guy has plenty of) and ask for his/her thoughts, and let them know that you've got too many closers (if they need saves). They might make you an offer that behooves both of you.

You may also try to call or instant message them. Many people have additional contact information on their league pages or Facebook accounts.
In the dynasty league that I've run for over 10 years now, we work to get rid of owners who are perpetually unresponsive. We (myself and the other commissioner) start with polite reminders, then we resort to shaming and then we ask them to leave. Unless you play in a league where trading is discouraged I wouldn't be concerned with being too overt with the public shaming; it works. I can't tell you how much more fun and competitive my league has become over the years as we've slowly rooted out the passive players.
How would you pitch to a team owner that is clearly out of the running? I'm in a pretty robust keeper league (40 man rosters, 15 keepers, 10 MiLs) and people are just loathe to cash out on a lost season despite how powerfully you can rebuild in this format.
1. Figure out what they like. Have they ever dumped before? What did they get in return when they did? What kind of players do they usually trade for?

2. Give them examples of other teams successful rebuilding and how it works. Sell them on the process.
Biggest thing I normally mention is the "first-mover advantage"; if you're the first guy who punts on the season, you get the first shot to trade for the best keepers. I usually decide before the season starts, that if I'm not #1-4 in projected earnings/profit before the auctions, I plan to ditch that year and start over. While that's extreme, it helps me finish #1/2 when I do go for it.