Fantasy 101: How to Design a Good Trade

David Fenko gives his key habits that make up a good trader.

Trading is simultaneously the most exhilarating and most frustrating activity during the season. Trades can take forever to make, between owners taking days to make decisions, getting stubborn on certain players, and just general insecurity about “winning the trade.” But when a trade does finally come together, it is one of the best feelings in fantasy baseball. We hear time and time again about the frustrations of trying to make trades, and not enough about the incredible trades we are able to make, and so hopefully this article will help you get over those obstacles and close more deals. Because coffee is for closers, and we all need our coffee. With that said, here’s what I’ve found makes a good trader.

Four Good Habits


Before engaging in any trade negotiations, it is prudent to take on four habits that demonstrate to your league that you actually take the time to make offers that are balanced. Those habits are:

  1. Roster Review – Have a solid understanding of the make-up of all rosters in your league and what you perceive each teams strengths and weaknesses to be.
  2. Find a Trade Partner(s) – You’ve decided to address a weakness on your roster, now it’s time to find someone to work with.
  3. Have Talking Points Ready – Understand the reasoning behind your trade offer and be willing to divulge your thought process with your partner(s).
  4. Communicate – Don’t just make an offer, engage the other owners in conversation.

1. Roster Review


The first habit is roster review. Technically, this should be the first two habits, since you will need to review your own roster and the rosters of all of your league-mates. When reviewing your roster, there is a set of questions you should be asking yourself (this list is in no way exhaustive, but it is a start).

  1. How do you, as an individual, rate each player on your team?
    • For instance, let’s imagine that you owned Luis Severino at the end of April last season. In 2017 and early-2018, Severino was a top-10 SP asset. Potentially as a result of a deep playoff run in 2017, Severino struggled at the end of 2018, possibly a sign of fatigue. Early in Spring Training, Severino was shelved indefinitely with a shoulder strain, which may have been a factor to end the prior season. By the end of April, the news on Severino’s injury was pushing the rehab time further back into 2019, but without a clear sense of what was wrong. Severino owners were saddled with an asset that was both a league-winner and roster deadweight without a clear indication of which side of the coin it would be. As a Severino owner, before potentially including him in trade negotiations, you need to be clear with yourself on how you value him, to ensure that you get a return that matches that assessment.
  2. What are the strengths of your team? (Both in pre-draft ranks (this early in the season) and in actual performance)
  3. What are the weaknesses of your team?
  4. Which players are you trying to build around?
    • This might be the most valuable question. If you are in a redraft league, no player on your team should be considered a blanket no-trade type of piece. However, each league is different and you should know who on your team is who you want to build around and what their value is. Those players should be the ones you don’t consider in your trade proposals until you are deep in negotiations and you think you will bolster your team enough elsewhere to make up for your core strengths. If you are in a deep league and have two top-10 SP, you are at a distinct strategic advantage against the rest of the league at starting pitcher and you should look to maintain that advantage.

The above questions should be answered for each other team in your league (from your perspective). Going into any trade discussions, you should have an idea about what positions your league-mate might be willing to deal from, deal for, consider premium, etc. so that you can talk to those points when making an offer. Best yet, if you see something in your conversations that is indicative that your competitor has a lower opinion on a player you really like, you could come out ahead while actually trading to parity.

Roster review should be done somewhat regularly; I recommend at least once a week. I like to look at it either Sunday night, or sometime on Monday, once we’ve seen the results of the week and where everyone currently is in the standings. However, you need to be ready to deal at all times during the week. You never know when an injury could hit or a prospect could get called up; that could drastically change how someone feels about their team in an instant.

2. Finding a Suitor


The second habit is to always look for trade matches. After going through the process of considering the make-up of every team in the league, you should know where you are weakest and where other teams are strongest. You should also know if you have a strength that aligns with another team’s weakness, and goodness willing, you are strong where one team is weak and they are also strong where you are weak. In cases where there isn’t a 1:1 match between teams, don’t be shy about engaging multiple owners for deals towards the end of a three-way trade. There is a good chance that you could align trades between two other owners just by virtue of completing your own assessment of the league. I know many of the major sites don’t support three-way trades, but I’ve never had an issue with notifying the league and just working around it by processing multiple trades as a work-around for that issue.


3. Crafting a Narrative


The third habit is creating a narrative. You’ve consumed a lot of information over the course of the week, just based on roster construction alone. Before you make an offer, put together a convincing argument for the other owner that demonstrates that you put together the offer with care and consideration for their position. Research plate appearances, innings pitched, and starts and use that information to make your players look better (or their players look worse, or all players being comparable). Be willing to parrot what coaches and pundits are saying about players. Provide insight into players that may be dropped in an unbalanced trade to show that you understand that no unbalanced deal is standalone. The extra care you take in putting together the narrative should help you provide transparency into your process so that the other team doesn’t feel like they are being taken advantage of.


4. Cultivating the Conversation


A little bit (ok, maybe a lot) of work upfront will make trade negotiations easier and more productive. Be willing to put in the effort where you can to make the experience good for all parties. A well-researched trade negotiation tends to pay back at that moment, and again in the future, as owners will pursue you for trades because they understand you are willing to put in the legwork. In my experience, stalled trades may even reappear when circumstances change as a result, just because of all of the considerate conversation that has already taken place.

Applying the Habits


So let’s put all this together, shall we? Here’s an example from the 2019 season:

I’m trying to get Eddie Rosario in my redraft league to improve my outfield. My current outfielders are George Springer, Mallex Smith, and Franmil Reyes, with no outfielders on my bench. I do have three third basemen on my roster, Eugenio Suarez, Josh Donaldson, and Mike Moustakas.

The current offer from the Rosario owner is Eddie Rosario for Eugenio Suarez.

Right off the bat, we’re missing some key pieces of information, mainly a clear picture of the teams’ strengths (because only starters have been named), and any information about the other team beyond their ownership of Eddie Rosario. In order to resolve that information gap, I asked the questioner four things:

  1. What does the rest of your roster look like?
  2. What does the rest of the Rosario owners roster look like?
  3. Who are the best hitters on the waiver wire?
  4. How many teams are in the league?

The rosters were as follows:


Making a Trade


With all this detail in mind, and taking into account that the waiver wire did not have any inspiring options, my first thought was that Suarez was an overpay for Rosario. Keep in mind, this trade was proposed near the end of July, so Suarez had just hit about 12 home runs in the last 30 days and was slugging over .700 in the month of July. He seemed to really have put it all together. That said, Donaldson or Moustakas might have been viewed as an underpay. It was close enough that I floated that idea out there first, but figured I’d need to find a 2-for-1 deal to make it happen.

My first attempt was to try and make the trade Eugenio Suarez for Eddie Rosario and Josh Bell. This negotiation began with me asking what the other owner would want for Rosario, and he opened with Suarez, so I figure that he has interest in Suarez. With Abreu and Bell both being eligible at 1B only, I thought that perhaps the other owner would consider Bell expendable, especially since he had him in the utility slot and not the first base slot. I was worried about Voit’s health, and was thinking I could kill two birds with one stone and shore up two positions at once. Bell had also cooled off after his hot start, and so I was hoping that would sow some doubt in the other owner’s mind.

It turns out that the other owner had a similar feeling on Bell that I did, and thought that was too much. They considered the deal and said they liked the overall structure of the deal, but that the package of Rosario and Bell was just too rich for Suarez. I continued to look over his roster and saw Nicholas Castellanos, who was heavily rumored to being on the trade market. Castellanos had shown that he was a talented hitter, and I was hoping a change of scenery and perhaps a more competitive offense would ignite a spark in him. While this wouldn’t help my issues at first base, it would give me outfield depth that I’ve sorely been lacking and would allow me to not have to rely on Mallex Smith or Franmil Reyes. The other owner let me know he’d think about it when he saw my proposal. I was hoping for a more immediate answer.

Since I’d be getting two hitters back, and I already had two hitters on my bench, I knew I’d be cutting a hitter. During our negotiations, which I always conduct by actually messaging back and forth with the other owner, I heard that he was looking for second basemen on the trade market. To help the deal along, I offered to sweeten the pot by including Rougned Odor, noticing that he only had Ryan McMahon who could play 2B. Odor may not be the best 2B, but he hits for power and plays every day, and secretly, he was the player I would have cut if the deal went through. The other owner said that was enough for him, and the deal was made.

One item to note is that your mileage may vary. I was bullish on Bell and less so on Castellanos, but I’m willing to bet looking back on it now that my opponent wishes he had taken the first offer with Bell instead of Castellanos. You might think that Suarez was worth more, or that Rosario was worth more, and that’s all perfectly fine. Trades happen when you are higher on someone that someone else is lower on and vice versa. Trades will always end up being influenced by how we, as individuals, rank players. And that’s why it’s always good to have trade discussions, because the more you can discover about your opponent’s preferences and rankings, the better off you’ll be when making trades.

Featured Image by Justin Paradis (@FreshMeatComm on Twitter)

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