Confessions of a Trade-aholic

My name is Justin and I am a trade-aholic.

In my 15 years of playing fantasy baseball, I have made a ton of trades. Some have been good, some bad. It is easy for my league mates to remember the good ones, the ones that won me championships. Not too long ago, I turned Kennys Vargas and some draft picks into Madison Bumgarner in the course of a few trades. It was magical. I was the talk of the league. However, it gave me a reputation. To this day, there are people that are reluctant to trade with me in that league. In another league, I was not asked to come back because of “my style of play.”

The trade deadline is approaching in the majority of leagues, so I have spent some time developing some rules to live by when it comes to trading. Now there are always exceptions to every rule and not everyone will apply to every person, but here are some of the pitfalls and mistakes I have made or have seen others make.

Win Your League Not the Trade

When you are in a poker tournament and someone else is all-in, you are supposed to stop betting unless you hit an unbeatable hand. The idea being that the end goal is to be the last man standing, not win every hand and you have a better chance of doing that with less people involved. The same can be applied for fantasy. Sometimes you don’t need to win every trade. Your league mates may think it is dumb to trade Giancarlo Stanton for Billy Hamilton, but if you have a surplus of power and speed puts you over the top, then it’s a move you have to make. Don’t be afraid to give too much, if you think it guarantees you a championship.

Flags Fly Forever

If you are in a keeper or dynasty league, prospects and young talent are all the rage. People tend to overvalue these players to their own detriment. If you are in the hunt for a championship, it is often the right move to sacrifice your future to win now. There are a couple of reasons for this. First, no one remembers who second place was, but everyone remembers champions. Second, tomorrow may never come. I was in a long time AL Only keeper league until this year. The league had been in existence for over 30 years and I had been in it for the last 15. I went all out this last season, trading away all my keepers for this season to win my second championship in three seasons. However, I was not invited back to the league this season. Am I bitter? Sure, but I won the money. Tomorrow is guaranteed. “You play to win the game.”

Make the First Offer

Way too often in trade talks people say this, “What do you want for Player X.” It is a way of gauging your opponent’s value on a player. However, in my experience, there is a benefit to making the first offer. The framework of the majority of trades begins with the first offer. Maybe it doesn’t get accepted right away, but typically the final product looks somewhat similar to the original offer. You want that power.

Know Your League

Some people like to haggle. Some people don’t have the time. Some people always want the best player in a deal. Some love prospects. Knowing what each person in your league values gives you a leg up in negotiations. Something I started doing this year is keeping a folder in my email of all trade offers I have made and received. It allows me to go back and see what players my league mates have been interested in the past and gives me the ability to better figure out who I am dealing with on the opposite side of the table. In an era of fantasy sports when you can often be playing with people you have never met in real life, it is good get to know your competition to the best of your ability. I always friend my league mates on facebook and follow them on twitter. They won’t come to me most of the time for help in our league, but I’ll be able to see when they tweet at other industry professionals.

Be Persistent, Not Annoying

Just because someone is not interested in this moment, doesn’t mean they won’t be later. I try and continuously check in with people. Far too often I see trades go down in leagues and half the league had no idea that certain players were available. Check in with your league mates on a regular basis to see what the availability of their players are. On the flip side of this, don’t be annoying about it. I play in a league where I get anywhere from 10-30 messages a day in the offseason. I love fantasy sports as much as the next guy, but come on! Most people have lives, be conscience of that.

Sometimes the Best Trade Is the One You Don’t Make

I love to trade. Those who are good at trading gain an advantage over those that are not. However, some people out there are trade junkies. Use trades to your advantage as a supplement to your team. You never HAVE to make a trade. If you are desperate, others will smell blood in the water.

The next few fall into the “don’t be that guy” category.

Don’t Offer Garbage

Nothing ruins a reputation quicker than being the guy that always sends awful trade offers. No, I do not want to give you Carlos Gonzalez for Santiago Casilla. I am usually pretty cordial about it, but that will end the conversation for me. There is nothing wrong with starting with a low-ball offer, but don’t start a negotiation by insulting your trade partner’s intelligence. Don’t be that guy.

Don’t Denigrate the Players You’re Trying to Acquire

Few things are more annoying than someone honestly telling you “that player sucks, you should trade him to me for cheap.” If he sucks so much, then why do you want him? Talking players down doesn’t lower their value as a player, it lowers your value as a trade partner. Sure, sometimes it is beneficial to keep your motives hidden, but don’t be that guy.

Do Not Offer Dumb 3-For-1s

Ever get this offer? “I will give you Martin Prado, Matt Duffy and Eduardo Escobar for Mike Trout.” Of course you have. There is always one guy in your league that will consistently offer quantity for quality. The only time that ever works is in the deepest of leagues. Don’t be that guy.

The One More Piece Guy

Some people live for the hunt. What they love about trades is the negotiations. They attempt to bleed you dry little by little. This is fine, but if you continuously ask for an extra piece, you can get a reputation for being greedy and annoying. Even worse is when people try and renegotiate already finished deals. A deal is a deal. Trying to add pieces afterwards or backing out of an agreement is bull. Don’t be that guy.


Trading Isn’t Just a Seduction, It’s Also a Relationship

When trading with a partner, it is important to remember that you are attempting to seduce the other person. Be gentle at first and turn it up a notch when need be. Make your partner feel like you are looking out for their needs as well as your own. Don’t be greedy. Taking advantage of them only works out once. Don’t publicly brag with your buddies that won a trade. It could embarrass the other party. If you get a bad reputation as a selfish trader, you may find yourself without a partner later on. Always cuddle after.

We hoped you liked reading Confessions of a Trade-aholic by Justin Mason!

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Justin is the co-host on The Sleeper and The Bust Podcast and writes for Rotographs covering the Roto Riteup as well as random topics that float into his juvenile brain. In addition to his work at Rotographs, Justin is the lead fantasy writer/analyst and co-owner for, owner of The Great Fantasy Baseball Invitational, and a fantasy football and baseball writer for Fantasy Alarm. He is also a certified addiction treatment counselor. Follow Justin on Twitter @JustinMasonFWFB.

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Justin is this just your pen name and your actually in my fantasy league?

Bravo on a great article!