There are a myriad of factors that determine whether a trade is fair and equitable, but the process of negotiating a deal can require a lot of work by both trade partners. Making trades in a fantasy baseball league is an art, not a science. It also requires a lot of due diligence and forethought. Of course, some deals can be consummated quickly when the stars align, but generally speaking there are many factors that should be considered before finally agreeing to a trade.

A trade is akin to a contract in that there must be an offer, acceptance and consideration exchanged. Making an offer or accepting a proposal should occur as a result of careful analysis of what your needs are at a particular time. It only makes sense to trade if you address a specific need and can afford to sacrifice something else as compensation. There is such a thing as over-managing in which fantasy owners trade for the sake of trading. While it is fun to negotiate trades and swap players, it can be counter-productive if you do so without a thoughtful plan in place.

Part of the reason trading is an art is because there is a bigger picture to consider. You must look at the entire season as a canvas and carefully think about what picture you are trying to paint. Impulsively reacting to a catastrophic injury or a week-long slump can lead to irrational decisions with long-term impact. This requires exercising restraint and remaining logical rather than reacting out of pure panic or desperation. You will be better served in the long run if you can take a breath, count to 10, and objectively ask yourself whether making a certain maneuver is what is really best for you.

Once you have addressed an area that requires improvement or depth, you will need to find a trade partner who has assets that you desire. Not only that, but ideally you want to trade with someone who has a glaring need as well. This means preying on those who are desperate. It is survival of the fittest so do not feel guilty for trying to take advantage of someone else’s misfortune. If an impact player on someone else’s team gets hurt, you should immediately begin evaluating whether you can prey on their desperation by utilizing such leverage in order to gain a more valuable asset.

Another important factor in trade negotiations is being realistic about the value of your own players. Anyone who attempts to strike a deal is going to try and obtain the most while giving up the least. That is human nature and there is nothing wrong with that. However, we must accept that everyone has their own subjective evaluation of players and they do not always mesh when discussing trades. We must admit that we tend to over-value our own players because of the inherent need to validate our own decision-making skills. It is safe to assume that your trade partner is doing the same thing. If you think their trade offer is insane, then chances are they think your counteroffer is as well. In order to break the impasse, you should evaluate your players as objectively as possible which will help progress the dialogue past insulting each other’s intelligence.

Accumulating depth and surplus on your roster is paramount to putting yourself in an advantageous trade position. Whether it is through the draft or on the waiver wire, you should be focused on building your roster with flexibility at all positions. This will not only allow you to withstand injuries, but you can avoid having to make a desperate trade and also utilize such depth in order to make trades that will improve your team in other areas.

Looking at the big picture when negotiating trades also requires taking some risk by selling valuable assets. Many trades are thwarted when fantasy owners balk at the idea of dealing elite players. If you spend an early round draft pick or significant auction dollars on a particular player, chances are you invested in him to be a cornerstone of your team for the season. However, one player alone does not win championships. You must be open to the idea of trading away star players if you can acquire several other players who provide improvement or depth at multiple positions. Leagues are not won or lost based on the first few players you draft. The key to success is building a balanced roster, so if you can obtain better balance by trading away one elite player than you need to remain open-minded to such a possibility.

After looking at the merits of potential deals to engage in, you must consider other intangible factors that are part and parcel to making trades. You should always reference your league’s rules to ensure that any trade you make is compliant with all roster and lineup requirements. If your league has a maximum number of players at certain positions allowed, then do not make a trade that would violate such limits. In addition, always consider your league’s scoring system when evaluating what trades to make. If you are in a roto league, take into account where you are in the standings in each category before making a trade because certain deals may not look advantageous on its face but may actually improve your team based on specific needs.

Then there is the concept of fantasy baseball etiquette. We all play fantasy baseball because we want to win, but let’s remember it is also fun and usually amongst friends, family, colleagues and acquaintances. It is very important to be respectful and courteous to your fellow league members because a large component of the fun factor is the interaction amongst everyone, whether you know each other or not. If someone takes the time to send you a trade offer, you should be courteous enough to respond in some capacity. One of the most frustrating things to experience in a fantasy league is an unanswered trade offer. Just because someone makes an offer does not mean you are compelled to negotiate a deal.

However, an offer should be responded to in some capacity and without insults or derogatory remarks no matter how outrageous the offer was. Even if you aren’t interested in making a trade at that time, a respectful response will open the door for dialogue later on when you may be interested in trading. People remember things like this, and you are more inclined to get a receptive response from someone you showed the proper respect.

Continuing the theme of trading with etiquette and within the rules, you should never collude with other league members when negotiating trades. Collusion is when two or more parties enter into a mutually beneficial agreement with a fraudulent purpose. Examples include orchestrating a one-sided trade, sharing prize money, manipulating the waiver wire, or intentionally playing a sub-standard lineup. Everyone wants to win but you need to do it the right way. Winning is certainly a key component to playing in fantasy baseball leagues, but it should not come at the expense of one’s integrity.

Finally, you need to look at the aftermath of a trade through a selfish lens. No one wants to have buyer’s remorse when a player traded away blossoms for someone else and the player you acquired becomes a star like Jason Bay once was. However, it is quite possible that a trade benefits both teams and you cannot second guess yourself if your trade partner succeeds as a result. You have to look at how the trade affects your own team, and your roster is improved then that is all that should matter.