DISCLAIMER: this article is about the art of making fantasy football trades and not engaging in multi-million-dollar real estate deals.  I just wanted to be clear about that to avoid any cease-and-desist letters from Donald Trump’s lawyers because we know the Presidential candidate is reading this since he gets all of his fantasy football advice from Fantasy Alarm.  Now that we have taken care of that, we can get to the business at hand. 

As the Chief Justice of Fantasy Judgment, I evaluate hundreds of fantasy football trades every season to determine whether they should be approved or rejected based on a myriad of factors to conclude whether a trade is fair and equitable.  While the end result of the negotiations is what is submitted to the Court, there is a lot of work that goes into formulating the structure of a potential deal.  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. 

One of my mantras as an adjudicator of fantasy trades is that making a deal is an art, not a science.  That is because you must look at the big picture and avoid making impulsive decisions despite the temptation for a short-term fix.  So in order to help you perfect this art, here are some helpful hints to assist you in making fantasy football trades great again. 

1. Do not trade for the sake of trading.

The process of making a trade in a fantasy football league can be exhilarating.  You may be tempted to strike a deal simply because you assume you have to.  Do not fall victim to over-managing.  Simply because someone makes an offer does not mean you are compelled to negotiate a deal.  Only consider making a trade if it will improve your team because some of the best trades are the ones not made.  It only makes sense to trade if you are addressing a specific need while being able to afford to sacrifice something else as compensation.  While it is fun to negotiate trades and revamp your roster, it can also be counter-productive if you do so without a thoughtful plan in place.

2. Do not be afraid to trade a superstar.

Most standard leagues have 12-14 teams so every GM is going to have at least one elite player.  However, owning elite players does not guarantee success.  It is far more important to have a well-balanced roster, so you should be open to the possibility of trading a star player in exchange for several very good players.  This is part of the risk assessment that takes place when looking at the big picture throughout the course of the season.  There is a natural hesitation to trade away a superstar player because GMs have invested either an early round draft pick or significant auction dollars in that asset.  However, under most circumstances 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.  This will provide you with a more balanced roster and could help set you up for sustained success over the course of the season. 

3. Trade from a position of strength.

Building roster depth and flexibility is one of the primary goals heading into a draft and utilizing the waiver wire.  A surplus at a particular position can be used as trade bait to bolster other positions on your roster.  This is paramount to put yourself in an advantageous negotiating position with leverage.  Not only will you have the upper hand in negotiations, but roster depth will also allow you to withstand injuries and avoid having to make a desperate trade from a position of weakness.

4. Assess other teams’ weaknesses.

The best trade partner is a desperate GM.  Look at other rosters to see which GM suffered a catastrophic injury.  That team is more inclined to make a move out of desperation which increases leverage for a better return.  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.  It may seem aggressive to prey on those who are desperate, but this is survival of the fittest and you should not feel guilty for trying to take advantage of someone else’s misfortune. 

5. Be honest with yourself.

In order to consummate a trade, you need to be 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 should naturally be expected.  However, we must accept that everyone has their own subjective evaluation of players which does not always mesh when discussing trades.  We must admit that we tend to overvalue 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 someone else’s trade offer is insane, there is a high probability that they think your counteroffer is equally insane 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.

6. Understand your league’s rules.

You would be surprised how many trades Fantasy Judgment has rejected because the deal itself was in violation of the league’s own rules.  It is imperative that you be cognizant of what your league requires for a valid lineup and roster.  Do not make acquisitions which would cause a rules violation.  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.  Equally as important is to pay attention to your league’s scoring system because some players have different value depending on the setup (i.e., PPR vs. non-PPR).

7. Be respectful and courteous.

There is a such thing as fantasy football etiquette.  We all play fantasy football 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 GMs you know each other personally 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.

8. Do not collude.

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.  Continuing the theme of trading within the rules, you should NEVER collude with other league members when negotiating trades.  Winning is certainly a key component to playing in fantasy football leagues, but it should not come at the expense of one’s integrity.

9. Not every trade has a winner or loser.

As we discussed earlier, GMs inherently want to acquire the most while giving up the least in any trade.  However, improving your own team should be the top priority irrespective of whether the deal also improves your counterpart’s team.  You need to look at the aftermath of a trade through a selfish lens.  Of course no one wants to have seller’s remorse when a player traded away blossoms for someone else, but as long as the return you received helps your team it shouldn’t matter that someone else benefited as well.  

10. No league votes.

The Supreme Court of Fantasy Judgment has long lobbied against fantasy leagues that employ a voting system to approve trades.  As a broad generalization, these leagues are set up for disaster because GM’s have their own agendas and can easily block trades to prevent competition from improving.  Plus, there is no guarantee all league members will vote on the matter.  This process discourages trading within leagues and also calls into question the legitimacy of the process because self-interests will rule over meritorious decisions.  Commissioners should have the ultimate say in whether to approve or reject trades except when the commissioner himself/herself is involved in the deal.  The Court recommends having a process of checks and balances in place to have a co-commissioner or a small committee be able to review trades that the commissioner makes.  Of course I would be remiss if I didn’t also suggest an independent third-party service such as Fantasy Judgment which can handle these decisions for leagues and remove any possible improprieties. 

Michael A. Stein, Esq. is the Chief Justice of Fantasy Judgment, the industry's premier dispute resolution service, and co-host of the Fantasy Alarm Podcast.  You can contact him at michael.stein@fantasyjudgment.com or on Facebook and Twitter (@FantasyJudgment).