Trade strategy: Getting to know your opponent

The season is here! The Red Sox and A’s have played their first games and Opening Day in the States is nearly here. Your draft prep is complete, draft day has passed, and it’s time to relax, right? Well, no.

You have your team and the games are set to begin, but now it’s time to begin thinking about trading. Even if you don’t make your first trade until July… even if you don’t make your first trade until the day of the deadline (highly discouraged as that approach may be)… now is the time to begin laying the foundation.

If you know the enemy and know yourself you need not fear the results of a hundred battles.
— Sun Tzu

You’ll often read articles about fantasy baseball strategy that talk about “knowing your opponent.” Many times, though, there isn’t much elaboration on this point. Typically, the advice ends there.

Because of this, I thought I’d expand upon this vital concept in the context of trading.

I see the trading process as having four layers. The deeper you go, the more effort you have to put in. The deeper you go, however, the more successful you will be.

(Quick note: I will use a lot of masculine pronouns for simplicity’s sake. I realize that plenty of females play fantasy baseball, so please don’t take this is a slight.)

No. 1—The “me” layer

  • What do I want to give? What do I want to receive?

    The most basic tenet of trading. Every owner thinks about this. If he doesn’t, well, fantasy baseball probably isn’t for him.

No. 2—The “him” evaluation layer
  • What does my opponent want to give? What does my opponent want to receive?
  • What methods does my opponent use to value players?

    A little bit less common than the “me” layer, but still something a reasonable number of owners think about. That doesn’t make it any less important, though. If you had tried offering an owner in the… let’s say, Dusty Baker mold… a sabermetric darling like Jamie Shields for Barry Zito and his freshly signed contract last April, he might have laughed in your face.

  • Does he play favorites, maybe for players on his home town team?
  • Are there players he refuses to roster?

    If you can identify which types of players he overvalues, you might be able to get a better deal than you would otherwise. If you know that he refuses to take any, say, Yankees, then you’ll know what not to offer him.

  • What Websites does he frequent and what books has he read?

    Might be difficult to decipher, but if you can, this is very valuable information. Also, this isn’t restricted to books like the Hardball Times Baseball Annual; knowing if he reads books like the Art of War or the Book of Five Rings or even Harrington on Hold ‘Em is very important too.

  • Does he get attached to players?
  • Does he tend to overrate his own players and underrate everyone else’s?

    If the answer is yes, this is the type of owner you may want to stay away from if you can’t swing a deal quickly. He’ll take up a lot of your time and the deal probably won’t get done.

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  • Does he look for very specific players or is he more open?

    If he asks for Garrett Atkins, is Atkins the only player he will discuss, or will he entertain the idea of acquiring Chipper Jones instead?

  • Is he an active trader?
  • How many trades does he generally make per year (if you’ve played in a league with him before)
  • Does he make trades early in the year or wait until later?

    Active traders are much better partners than inactive traders. Knowing when your opponent makes trades can be critical as well. If he likes to make them early, you need to do this recon work much more quickly so that you can get in on the action. If he waits before making trades, use that time to gain intelligence on him and to butter him up for a later trade.

  • What time of year is it, and where is his team in the standings—overall and in each category?

    This can give you insights into the urgency (or lack thereof) he could be feeling to make a deal and the types of players he might be looking for.

  • Does he give up on players early, like in April or May?
  • Does he give up on players who are on a cold streak?
  • Does he ever tend to sell low?

    If an owner displays any of these tendencies, evaluate the under-performing players on his team, and if the skills and indicators are favorable, make a play for him.

  • Does he prefer quick conversations and quickly completed trades or drawn out, thought-driven negotiations?

No. 3—The “him” psychological layer
  • Does he view me as a strong or weak player? Somewhere in between?

    The stronger he views you as, the more reluctant he will be to trade with you. Nobody wants to get hustled.

  • How long has he played fantasy baseball? How long has he followed “regular” baseball? How big a baseball fan is he?

    Suppose this is his first year playing fantasy baseball, but he has followed “regular” baseball quite fervently for years. He probably knows his players pretty well, but he might not know the intricacies of strategy, negotiation and deception. If some of the other factors point this way, maybe simply being nice and helpful can swing a deal. Also, your own deceptive measures are less likely to be discovered. This could also be useful in that players who are good at baseball aren’t necessarily great fantasy players. Use that to your advantage in trade talks.

  • Have you dealt with this owner before? How have previous dealings went?
  • Do you know anything about previous dealings between him and other owners?
  • Has this owner been known to use dirty tactics or treachery in any way?

  • Does this owner have a background in anything useful for fantasy baseball purposes? Business, psychology, military strategy, poker, etc.?

    If he does, pay attention to ways in which he might be using these skills.

  • What is this owner’s personality like?
  • Is he aggressive? Laid back?
  • Does he have a big ego?
  • Is he insecure in life? Is he insecure in his ability to run a fantasy team?
  • Is he extremely skeptical and distrustful of everything you say, possibly seated in some type of insecurity?

    Is the player always thinking you’re out to get him or always thinking that you know something that he doesn’t? Is he so much this way that he mistrusts even simple statistics you place before him, or is he open to logical suggestion? If an owner is the former—which could likely be discovered early if he shows signs of insecurity and lack of any semblance of an ego —e is likely a very weak player, but probably one you shouldn’t waste too much time on. He’ll always think you’re getting the better of him and will refuse to trade for that reason.

  • How emotional is he?

    Emotions can be very important, as talked about in this article.

  • How secretive is he? Can he be prodded into revealing information?
  • Is he willing to give more information, either about his strategy, player evaluation techniques, or specific players, when he is more emotional?
  • What is the best way to make him emotional?

    If he is willing to give information, try to get it out of him. Having intelligence on how to get him emotional can be very important in this regard. Just remember to do it cautiously and sparingly. If he catches on to what you’re doing, this tactic will be much more difficult to perform on him in the future.

  • Is he very impulsive or more likely to be rational?
  • Is he more likely to be impulsive when his emotions flare up?

    If so, build up to the point where a trade is nearly complete, and then see if you can’t get those emotions into action.

  • What is his current mindset, the day you are talking to him? Is he feeling deflated about his team?

    If he’s down on his team, now could be the time to grab a couple of his players who are getting unlucky.

  • How receptive is he to the hard sell?
  • How hard can you press him before he gets really angry and retreats from negotiations?

    If you press too hard, it could hurt not only the current negotiations, but he could refuse to negotiate with you in the future. At the very least, he could go into future negotiations more close-minded.

  • What is he most receptive to? Logic? Intimidation? Simple kindness? Acts of weakness on your part? Maybe some massaging of his ego?

    Find out what it is and discretely take that approach. Be aware of possible changes in what he is receptive to and adjust accordingly.

  • How opinionated is he? Is he constantly talking about what he thinks about players? Does he refuse to ever talk about players?

    Be aware of noticeable changes in this area. If an owner who is generally tight-lipped about players he likes all of a sudden starts talking about how great one of his players is, consider that he might be trying to dump him, even if his reasons seem logical.

  • How aggressive is he?
  • Does he go for the home run every time, or is he more content to compromise?

    Owners who look to make only “fair trades” are easier to deal with than those who will make a deal only if it is a blatant rip-off. Dealing with a “fair trade” owner also makes it more likely you will end up ripping him off if there is some flaw in his evaluation of players.

No. 4—The “him” danger layer
  • Is he analyzing me in this way?
  • Does he have reason to believe I’m analyzing him in this way?
  • Is he a creative, strategic, independent thinker?

    If you answer yes to these questions, you are dealing with an extremely dangerous opponent. If he is thinking about you in this way, and he concludes that you are thinking about him in this way, things can get very tricky. Intricate mind games can come into play. If you are dealing with this type of opponent, you always want to try to think several steps ahead of him. Beware, though, because he is likely doing exactly the same thing.

  • Could he be feeding me false information?

    Counter-intelligence is a complex topic, but when used correctly can be a deadly weapon. It is a topic that we will need to talk about in more depth in the future, but identifying owners who are using it (and how well they are using it) can be crucial. These owners need to be approached with the utmost caution, and you need to be very careful when deciphering what information is real and what is a facade.

Make a record of every conversation you have with your opponents, if possible, for future reference. This should be easy if conversations are conducted via email or instant message.

Knowing yourself

Let’s revisit the Sun Tzu quote at the beginning of this article: “If you know the enemy and know yourself you need not fear the results of a hundred battles.” We just talked about knowing your opponent in great detail, but also of vital importance is knowing yourself.

It can be good practice to run through these questions with yourself as the subject. Really get to know what drives you in the game of fantasy baseball, in negotiations, and psychologically. You might find you unearth some unintentional tendencies you have that your opponents can exploit. Once you find them, you will know to conceal them.

Think about this in terms of poker. There are two key elements to a good poker player. One is math, odds and probabilities. The other is reading your opponents’ tells and concealing your own.

If you’ve ever seen the movie Rounders with Matt Damon, Edward Norton and John Malkovich, you’ll recall that Malkovich’s character, Teddy KGB, had a very distinguishable tell. He had a box of Oreos, and he would crack one open and hold it up to his ear. When he ate the Oreo, he had a good hand. When he didn’t eat the Oreo, he was bluffing. Matt Damon’s character was able to figure this out and use it against him. Had Teddy KGB analyzed himself, he would have recognized this tell and could have stopped it.

Obviously tells at a real poker table aren’t this obvious, and tells in trade negotiations are probably less so, but it doesn’t necessarily have to be a mannerism. If you can read people in this way, fantastic. If not, simply collecting information and running a careful analysis of it can be enough. This includes running an analysis of yourself and hiding any exploitable tendencies you have.

Achieving success

To be successful, you need to look at the institution of trading as a war. You need to look at every competitor as an enemy. You need to look at every conversation you have with another owner—even those where the discussion isn’t baseball related—as a means of gathering intelligence. You need to look at every negotiation you have as a battle.

You then need to consider that the best generals in war, the best strategists, are the ones that are flexible. If you can adapt to your various opponents’ strengths and weaknesses, you will be better able to overcome him.

I’ve talked about Miyamoto Musashi once before, and he makes for an excellent subject once again.

Musashi and his enemies

Musashi was a young Japanese swordsman. He had previously fought two duels with members of the Yoshioka family. At each duel, he showed up late to anger his opponent. He defeated each. When a third member of the family challenged him to a duel, Musashi used this intelligence to adapt to the situation, creating an innovative strategy.

Instead of showing up late, he came very early. He waited in a tree for his opponent to arrive. His opponent, angered with Musashi’s previous disrespectful actions, brought along a small army. As Musashi was nowhere to be seen, his enemy assumed that he would arrive late, as he did at his previous two battles. He and the army lay down in wait. Musashi jumped out of the tree and killed the disoriented men.

Soon after, Musashi found another suitable challenge, a warrior named Baiken. Baiken was known for using a sickle and a long chain with a steel ball attached to the end. Baiken would begin the duel by swinging the chain, forcing his opponent backward and off-balance. He would then throw the ball at his enemy, who would be forced to deflect it. When he did, Baiken would kill him with the sickle.

Musashi brought one short sword and one long sword to the duel, something no one had done against Baiken. Baiken became reluctant to throw the ball at Musashi, because he could deflect it with one sword and strike him with the other. Upon the start of the duel, Musashi charged Baiken, who was unable to build up momentum with the ball. He knocked him off balance with the short sword and struck with the long, killing him.

In a third duel, Musashi played on his opponent’s emotions. Facing one of the greatest warriors in a country known for its customs, Musashi arrived very late, lying down in a boat, whittling a piece of wood that he would use as a sword. As he got off the boat, he tied a dirty towel to his head as a headband. His attitude was extremely cocky, and he made nonsensical remarks that further infuriated his enemy. This caused his enemy to make a careless mistake in battle that afforded Musashi an opportunity to defeat him.

Adapting to your enemy

Musashi understood the importance of adapting to his enemy. He would discover his enemy’s weakness and would exploit it. This is exactly what we must do with our trading partners. We must collect as much information as possible about them, and then use the approach that will be most effective. This will change from person to person, and it may even change for the same person on occasion. We must always be aware and attentive. It is easy to simply send a generic trade offer via e-mail, but without knowledge of your opponent, its chances for success are relatively slim.

Concluding thoughts

If you think I failed to include useful information a trading owner should seek, feel free to send me an e-mail. As Lenny Melnick recently said, “Trading is a definite art.” It is more art than science, and when it comes to intelligence gathering, you can never have enough. I am sure that I left some potential questions out. If I get some good ones from you, I’ll be sure to make a post with them.

On a completely unrelated note, I’ll be a guest on Elliott Price’s radio show this Sunday at 2 pm EDT. Elliot Price is a former play-by-play announcer for the Montreal Expos. If you’re interested in listening, I believe you can access it at

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