There is a moment of dread that almost all fantasy baseball owners have faced, the moment when you are informed that a player you have been intending on targeting gets traded to another team. The metaphorical sibling of this moment is when you are informed that player has been traded and at that moment you realize that you should have been targeting that player, especially given the price tag. The typical response to such a trade usually goes like this (I have removed the profanity and replaced it with the meaning behind the profanity): “That’s really unfair, Team X did not get enough in return.” The best part follows: “I would have given Team X more for that player/those players.” Sometimes, we even get the cherry on top: “Well, we can all pack it in now and hand the trophy to Team Y (the trade partner of Team X).”

Allegedly unbalanced trades usually result in complaints of injustice from team owners who were not involved with the trade and even end up with owners trying to veto trades (my solution: do not play in leagues with vetoes). This is typical human response: Get worked up about unfairness and demand fairness, but do not attempt to fix the root cause, especially when the fixing involves action on our behalf. J.P. Breen (smart dude) sums this phenomenon up nicely in these two tweets:

Humans prefer justice over improvement; we prefer to complain about the actions of others than to find ways to improve ourselves. Instead of working harder at finding trade opportunities or initiating trade talk, we would rather call the trades that others make unfair. If we are complaining about a trade, it almost always means we were outhustled. The assumption here is that we liked the trade for one team, but not the other; therefore, we would have offered as much and maybe even slightly more to be on the preferred side of the trade. Such misses stem from either failing to recognize an opportunity or failing to properly engage in trade talks. Really, we only have ourselves to blame.

But I do not write this to chastise, I write this with the hope that we can improve. What follows are recommendations that will either help us be on the envious side of trades or at the very least, help drive up the price for desired trade targets (by increasing demand).

Effort trumps skill
Regarding trades, I define effort as the work done to find trade opportunities and skill as the ability to win a trade or get the most out of a trade. In my experience, skill tends to get all the attention and glory, but effort produces more value. I usually find that the owners that gain the most value through trades are the most active owners. These owners are not necessarily the best negotiators and they certainly do not “win” every trade, but they are able to capitalize on opportunities (make trades) more frequently than their competition. This is the case because finding out that a valuable asset is available and, consequently, acquiring that asset brings in more value than having the skill to negotiate the best possible deal for that asset.

Analogy: 10 fishing boats with average fisherman will yield more fish than one fishing boat with good fishermen. Sure the one boat will have the best efficiency, but the ten boats will catch the most fish. Luckily we do not have to pay for boat insurance in fantasy baseball; instead, we can focus on getting the most lines in the water and spend our time searching for catchable fish.

Do your homework
While effort is the start of the process, blind effort is not very helpful. Consequently, we need preparation. For most keeper and dynasty leagues, the time to prepare is now. Because most offseason trade markets do not heat up until the winter meetings, now is the best time to find out where each team stands, what each team has, and what each team needs. I know when I first started playing fantasy sports, I spent the most amount of time focusing on my team, its assets, and its needs, but I found that knowing the same for my opponents was equally if not more important. (Poker players will see that this logic comes almost straight from poker strategy, where it is more important to know what your opponent is holding than it is to know the cards in your own hand.)

I also recommend spending extra time looking at unfamiliar trade partners (owners that you have not traded with much or at all). We are more likely to repeat past actions than undertake new actions; consequently, we are more likely to miss opportunities that are outside of our normal trade network.

Keep options open
Preparation directs us to where we should start our trade talks. However, it is important to not let our assumptions limit our trade talks. We might start by offering one of our extra closers for one of Owner
Z’s extra hitters, but Owner Z may very well be interested in moving a player that we did not expect, a player that we have interest in. This a tough line to walk because starting trade talk too vaguely usually leads nowhere and looks like you are fishing for offers, but starting trade talk with too narrow a focus can cause us to miss out on opportunities. Lastly, it is important to check our assumptions about what we think our opponents will be interested in. We might think Player A is our best fringe keeper, but there is a good chance that other owners think that Player B or C are our best fringe keepers. I find it helpful to structure trade offers and discussion in a way that potential trade partners can indicate which players they prefer. It would be easier to just ask, but often owners do not want to share their preferences in such a direct manner.

Most importantly, get studying and get hustling before your league-mates start plucking the players you want. Oh, and enjoy the playoffs.

Thank you for reading

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The point about knowing what your opponent needs is excellent. Never thought about it that way before during the offseason - something I didn't really look at until I identified an asset I wanted from the other team. This is very helpful advice.
Thank you. Good luck.
Excellent article! Really appreciated the comment about effort having more value than skill. Great great read
Great article. I have one quibble, though: I find that the people who complain the most about trades aren't usually people who would actually have offered more for the players the "winner" got. It's more often people who would have or did offer less for the players the "loser" got.

People who look at a trade and think "I would have offered more for those guys" need start talking to other owners more to find those opportunities, but people who think "he should have had to pay more for those guys" or "he totally overpayed for those guys" are not looking to make more trades, they are looking to add a social "tax" onto trading that prevents other owners from gaining the value they are missing out on. Often this is because they are either gun-shy themselves or don't have as good a relationship with certain owners and therefore feel left out.
I agree, I almost wrote about this sub group of complainers, the ones who complain, but would not have matched either side of the offer. These owners are the worst. I really like your term "social tax"; we could also call it bullying (they tend to be the gun shy ones).

I wrote about "trade paralysis" earlier this season, which pertains more to these types (although, this article's "we only have ourselves to blame" also pertains to them).
I've been trying to apply these principles for the last several years. A lot of incremental improvements can add up to big gains. But to be able to find a lot of these little improvements I am working my butt off to know more about the other guy's roster than he does.

Heck, I had one guy respond to an offer with "You probably know my roster better than I do; I haven't really looked at it for a while. Sounds fair. Let's do it."

Also, knowing their expected place in the standings help too. If you can identify the expected bottom teams quickly you may be able to pull in an older useful player before others ask about them.

And knowing their biases is a big deal too. Knowing if they like lottery tickets, players from team-X, or pitching over offense can go a long ways towards pulling off a lot of deals.

So I agree, you don't have to be the best to get good results, just be willing to work hard.
Absolutely, knowing who is buying and selling definitely helps. I have also found that there are opportunities to trade with teams that are not easily recognizable as buyers or sellers (the middle teams), as some owners disregard them, assuming they will not buy or sell.