The “Art” of the Fantasy Baseball Trade

Sun Tzu  - The original master of the Fantasy Baseball Trade

Sun Tzu – The original master of the Fantasy Baseball Trade


Several hundred years ago a Chinese military general named Sun Tzu wrote one of the most influential books in modern history, a strategy piece called “The Art of War”.  The book outlined the way to manage conflicts and win battles, describing war as an art-form. Tzu also touched on diplomacy and cultivating relationships and why that is important to success.  I am certainly no great historical figure, but I wanted to pass along to fantasy baseball managers a little about what I have learned regarding the “art” of trading and demonstrate how some of Tzu’s principles can be applied to fantasy baseball (sounds a little strange, but keep reading, I promise I’m not insane).


One of the main themes of Tzu’s book was that war is a necessary evil that should be avoided whenever possible. Similar to this, trading should never really be encouraged, unless the circumstances either force you to do so (if you have an injured player) or you if you wish to take advantage of a particular manager or situation (selling high on a player or trading with a particularly inept person). Trading involves a great deal of work and a particular set of conditions to be met, since without the right trading partner or players involved, a deal is unlikely to happen. Have faith in the team which you initially drafted, since too often managers will cut bait with players and sell themselves short. Patience is a virtue, and sometimes riding out the storm through a tough slump will be more beneficial than trading away someone too soon.


“Know thy enemy and know thyself” – Trading is much easier when both managers understand upfront what each other wants. If you wish to trade a relief pitcher in exchange for a batter, don’t just blindly send a trade to each manager in the league in the hopes that someone responds to you. Start off by examining each of the rosters and seeing which manager is currently short on relievers. Did someone punt saves but is having second thoughts? Did you happen to grab the closer off of the waiver wire that your friend really wanted? Make sure that you go into a trade from the outset knowing that you are offering something that the other player wants, and aren’t simply offering a trade because you were bored.


Exercise common courtesy when you trade as well. If you are going to be the manager to initiate a trade, don’t tell the other party to send you something to review. Take the time to do some research and make an intelligent offer. Deals will commonly get shot down because a manager either offers a completely ridiculous unbalanced trade (which is a MAJOR pet peeve of most players) or because the person who is looking to trade is too lazy to put in the work to get a deal done. Don’t rely on other managers to close the deal, take a few minutes and do some research, it will make things go MUCH faster in the long run.


Knowing your own tendencies is key as well. Is someone offering you a trade for a rookie who you are particularly high on? Will your emotions cloud your judgment and make you pay too much? Is someone offering you a player on your favorite team? Will hometown bias make you regret it? In a perfect world, if you are offered a trade, take a moment to think about both the long-term and short-term benefits, rather than pulling the trigger right away. If you are the one offering the trade, attempt to get your partner to accept as soon as possible.


Be extremely subtle, even to the point of formlessness. Be extremely mysterious, even to the point of soundlessness” – When you are trading with another manager, you ideally don’t to show your cards right away. If you are attempting to buy low on a player because you think that they have a ton of upside and will turn it around, it is best not to come out and directly say that. Experienced players will most likely understand right away the reason that you are attempting to make a trade, but attempting to be discreet is always a good thing.


If you go into a trade and tell a manager that you think that player X will start to play well, that could potentially cause them to second-guess dealing them. On the other hand, if you’re attempting to sell high on a player, you might want to make it seem that you’re doing the other player a favor trading them away. The standard is that you always want to “buy low and sell high” on players. Identifying buy-low candidates is only half the battle, since if you lead on to the other owner that you’re attempting to fleece them, you might kill the trade before it starts. If at all possible, attempt to hide your intentions about the player you are either dealing or acquiring.


Pretend inferiority and encourage their arrogance” – Always present a deal and highlight the points that will make the other manager feel that they are coming away with the better end of the trade. If your trading partner feels that they are benefiting more than you, the deal is likely to be completed faster. I’ve always found that in addition to sending a trade offer over your provider’s website, it helps to leave a little explanation as to why you want to make the trade. Here’s an example:


Player A really wants to trade away Adam Dunn because he’s killing their batting average category and is in need of a pitcher. When offering a trade to Player B, he should highlight Dunn’s power upside and on base percentage totals, and explain what a benefit he’d bring to the other team. Always highlight the positives of the trade to the other player. This isn’t to say that they won’t be keen enough to know that Dunn is a wasteland at batting average, but their initial perception will be the benefits, rather than the negatives. Since the positives will be the first thing that they are presented with, it has the chance to stick in their mind and sway their opinion.


The same holds true on the other side. Examining that same deal, if Player B counters with Yovani Gallardo (or whomever), then Player A should subtlety bring up the detriments that pitcher brings in the hopes of being offered someone of higher value. Poking holes in the player that you are offered both gives you perspective on the player that you are acquiring and opens the door for the other manager to sweeten the trade. Going back and forth through discussions with ultimately enable you to meet  in the middle faster on common ground.


The general who wins the battle makes many calculations before the battle is even fought” – As with many things in life, going into a situation as prepared as you can possibly be will always result in the best outcome. Don’t make trades out of a whim, and target the players who you feel will bring you the most success for the rest of the season. Go into trades thinking about both the short and long-term ramifications. Here is a prime example:


Two players who have started the 2013 season incredibly hot are Evan Gattis (C/OF – Atlanta Braves) and John Buck (C- New York Mets). They have been the topic of many talk shows and chat sessions that I’ve read, and overzealous managers are in a rush to get these players on their team as soon as possible. A wise manager would recognize that both of these players have huge flaws, and although the short-term outlook is positive on both, down the road it may not be a good idea to trade for them.


In the case of Gattis, he’s currently seeing playing time since Brian McCann is on the DL and will be sidelined for another month. Gattis made the ballclub thanks to a very strong spring training, and also qualifies in the outfield. When McCann comes back in a month, Gattis will likely be relegated to the bench and won’t get nearly as many at bats. Barring another injury, he won’t push either of the Upton brothers or Jason Heyward in the outfield, and McCann is the established veteran and clubhouse leader. So even though he’ll be useful for a month, he won’t bring much upside for the remainder of the season.


With Buck, the Mets currently have one of the best catching prospects in all of baseball in the minor leagues with Travis D’Arnaud. Unless they make a trade and he’s used as one of the main chips, the Mets will likely call him up in a few months and look to trade Buck. Again, managers should consider if the pros outweigh the cons on dealing for these players. A savvy manager that owns either of them may be attempting to trade now, while their value couldn’t be any higher. Taking a step back and examining how each player will benefit you for the ENTIRE season is crucial.


Keeping the long-term outlook of a player in mind is even more critical in the case of a keeper league, where managers will have the opportunity of carrying over players from year to year. Although I don’t expect 2013 to resemble 2012 in terms of the rookies having such an impact, players like Will Myers and Dylan Bundy carry significant upside for years to come. A wise player may consider trading an established veteran for promising young talent in the hopes of being rewarded for years.


To sum it up into easy steps:

  1. Do your research ahead of time.
  2. Find a trading partner who will benefit on what you are offering.
  3. Present the deal as if the other manager will receive the better end of the trade.
  4. Examine the player that you are getting and understand both the long- and short-term upside.
  5. Make the trade!


I’m not sure if Tzu was in a keeper league or how many championships he won, but it turns out that he knows a thing or two about making fantasy baseball trades.


A veteran fantasy sports player/commissioner for the better part of a decade, I am a contributing writer for several major fantasy websites including, and I am always willing to share my advice and opinions on your questions and the latest fantasy news. Feel free to contact me with any sports related inquires on twitter @Roto_Wizard, or by e-mail at

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One Response to 'The “Art” of the Fantasy Baseball Trade'

  1. Matthew says:

    One of the best write ups I’ve read this year. I will surely share

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