I have a confession to make: In fantasy baseball, trading doesn’t come easily to me.

When I started playing fantasy baseball, I took to auctioning relatively quickly. While I enjoyed trading, I frequently wound up on the shorter side of the deal. In some cases, this was simply due to bad luck after the trade, but more often than not, it was because I did a poor job and negotiated myself into an inferior deal.

Through experience, I have become much better at trading than I used to be. It will never be my strength, but over the years I have developed a core philosophy when it comes to making deals that has turned me from a poor trader into an above-average one.

If you’re looking to improve your trading skills like I did, below are a few guidelines for embarking on that path. These guidelines won’t improve your trading game overnight, but they should help you become a capable wheeler-and-dealer in the long term.

Engage With Other Owners

Many years ago, this advice wouldn’t have been necessary. Way back in the days before fantasy (mostly) supplanted Rotisserie, league members would talk on the phone to one another or even meet in person now and again. E-mail eventually replaced the phone as the primary form of contact, but even then there was still a healthy rapport with most owners. If you spent an hour or two discussing baseball with another owner over the course of the regular season, you had a pretty solid idea of who he liked, who he didn’t like, and what kind of deals you might be able to make.

In a lot of leagues, you now have the option of using your stat service’s web platform to offer and decline trades. While this is a useful tool and is certainly a time-saver, these trade tools give you the option to avoid human contact entirely. I can’t argue against the ease and convenience of having the ability to offer trades through your league’s web site, but you are really missing out if you don’t engage your other owners. To me, this is the difference between playing video poker and sitting at a poker table with other people. Video poker teaches you the mechanics of the game, but not the skills you need to thrive in head-to-head competition. You’ll get more out of your trades if you talk to other owners, and are more likely to pluck a player from an opponent if you get the conversation flowing.

Identify Your Goals

Why do you want to make a trade? Did an injury leave you short in a category? Did a cheap middle reliever turn into a closer, leaving you with a surplus in saves that you can leverage to your advantage? Is your team falling out of contention, leaving you in a position where it’s time to play for next year? This point might sound intuitive, but it surprises me how often another owner will reach out to talk trade without any idea of what he’s trying to do. You probably won’t get everything you want in a trade with another owner, but if you don’t know what you want to do before you enter the negotiation, you definitely won’t.

Establish Baselines

It is good to say that you want to trade a power hitter for a frontline starting pitcher, but this should be the beginning of your thought process, not the end product. If you’re willing to deal Josh Hamilton and your opponent won’t deal you Max Scherzer, is there a lesser pitcher you would be willing to take? Would you be willing to do a two-for-one with a lesser pitcher and a hitter to make up for some of the offense you will be losing for Hamilton? Or—based on your opponent’s roster—does it have to be Scherzer? Knowing what you will and won’t accept before you even start negotiating is key to not giving up too much in a trade. This isn’t to say that you don’t want to be flexible, but you should have a broad idea of how much value you want to get for your commodity before you enter the negotiation.

People Like Their Players

There is a strong chance that your initial offer is going to be rejected. We generally draft or buy players that we like, so why wouldn’t this be true for every other owner in your league? If someone is asking for “too much” for a player, it might not be because he is trying to rip you off but because he thinks more highly of his player than you do. Don’t overpay because of this, but keep this in mind before you get insulted and walk away from the table.

There Is No “I” in Trade

One of the biggest mistakes I see owners make at the outset of trade negotiations is spending a lot of time discussing what their needs are rather than focusing on their opponent’s needs. Obviously, both teams are trying to improve their standing in a deal, so I don’t need to know why a deal helps you or what’s in it for you. But I do need to know what’s in it for me. If you’re the one approaching me with a deal, you had better be able to explain why I should consider trading away my players. Telling me “I need steals and you have Everth Cabrera” isn’t a good reason for me to flip you Cabrera. On the other hand, if you start with “I see you have a lot of steals and are already first in steals; you could use power and I have J.J. Hardy,” you have a better chance of getting my attention.

Know Your Market, Know Your League

In many leagues, the trade market on Opening Day is different from the market on June 1. In Rotisserie-style leagues (as opposed to head-to-head formats), category gaps tend to lead to a changing dynamic in categories like steals or saves. Owners quickly figure out that they can ditch their lone closer and only lose a point or two. As a result, a quick trade for a closer for 75 cents on the dollar could happen. If your league is like this, definitely be aware and take advantage of the opportunity.

This mindset applies to many league rules that you can exploit if you understand your league’s unique dynamics. If you can trade FAAB dollars and work this in your favor, then do so. If there is a dumping mentality in your keeper league, make sure to judge your market correctly and not trade away your cheap keepers in fair deals while your opponents are cleaning up with owners focused on the future. In a new league, it takes time to figure these wrinkles out, but if you take the time the rewards are well worth it.

Don’t Be Afraid to Walk Away

For me, this is the most important rule of trading. It’s a cliché to say the best trades are the ones that never happen, but there is some truth to this old chestnut. If you enter a negotiation with the mentality that you have to make a deal, a savvy opponent will smell the whiff of desperation coming off of you. While it’s true that there might be situations where you are better off making a trade than not, you have to have a point where you realize that making a deal isn’t in your team’s best interests. This is especially true when another owner starts out with a terrible offer. Don’t bother trying to meet these obdurate personalities halfway, because halfway is almost always a bad deal if you are reaso

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The corollary to People Like Their Players – don’t tell the other owner how great your guy is or how bad his player is, let that owner decide on his own. Trying to sell one of your players as the next best thing since sliced bread or that the other owner’s player is garbage makes others wonder why you’re even trying to deal/acquire him. If you just stick with category-specific comments (i.e. you have a surplus in steals and I think you can use a SP) you will go a long way building a relationship, as to Mike’s first point.
I can't stand it when a an owner ASKS for one of my players then proceeds to TELL me all of his flaws in order to lower the price.

Either don't ask, or don't tell.
Here is some advice I gave for Scoresheet managers 10 years ago, but it all* still holds up as sound advice:

*There is no Scoresheet Canada anymore, but the advice remains the same.
Thanks to me! :)
"There's No I In Trade" is absolutely true, and I'm glad you mentioned it. Give the person a reason to trade with you.

Also, regarding People Liking Their Players: Every fantasy owner should learn about the endowment effect. To quote from the Wiki page: "People will pay more to retain something they own than to obtain something owned by someone else—even when there is no cause for attachment, or even if the item was only obtained minutes ago. This is due to the fact that once you own the item, forgoing it feels like a loss, and humans are loss-averse."

That is, the vast majority of the time you're facing an uphill battle. Coming at people with lowball offers will only reinforce this, and diminish your chances of getting what you want.

Both of these are why the "Three nickels for a quarter" offers are so frustrating.

Regarding Engage With Other Owners, if your league-mates are up for it, everyone get everyone elses' cell number. The number of trades and trade conversation via texting in my two leagues dwarfs all other communication combined. So fast, so easy.
That's incredible: making a trade over a text message. I don't doubt you, because I did it with someone in a league I just joined who was doing it by text. (I had to get my wife to send and receive the messages, because I don't even own a cell phone.) Would you make a trade without researching the players involved first with the latest reports and stats on them here, in FanGraphs, and in Rotoworld? Wow, I guess I'm an old foggie - I can't do things I care about on the fly like that.
100% agree. Love negotiating via text. Quick and to the point. Plus, 99% of the time its how you get a timely response.
Plus, for whatever reason it seems that prior discussion about a trade via text (or email) will lead to a better acceptance rate once you DO send the actual proposal (assuming Yahoo/ESPN platforms, etc). Often, even a fair trade proposal you just send will be rejected, but if you go thru the trouble to text/email and discuss it first....voila! Success. The rapport definitely helps.