Fantasy Baseball Trading Tips
How to have better trade conversations and close more deals
One of my favorite parts of fantasy baseball is not just talking trades, but actually making trades. I wouldn’t consider myself a good negotiator, but I have been able to make more trades recently, and I credit a lot of it to changing my approach and communication methods. Here are my tips on having trade conversations that actually result in closed deals.
(This is NOT about how to fleece your opponents or bully them into accepting your deals. Those owners suck, and if you want to win a league by picking on weaker owners, then congratulations on winning a league against weaker owners, I guess.)
Focus on what other owners want
You already know what your team needs. You follow your players’ results daily. You check out the standings to see where you could gain or lose points. You know which of your players are over- and under-performing. Enough. Trades are just as much about the other side as they are your side, and since there are way more teams in a league that aren’t yours, you’ve got a lot of work to do to understand every other teams’ needs as much as your own.
Don’t just spend half your time looking at other teams, spend 90% of your time looking at other teams. Understand their strengths and weakness, their path to improving, and how you could help them. Yes, you want to help them. Give them a reason to talk to you and an eventual reason to give you something. Show you aren’t going to waste their time. In fact, I wouldn’t start the conversation with a specific trade offer, or even what you’re looking for. Start with stating your understanding of what might help their team, asking for confirmation and if they have additional needs you haven’t mentioned. Then, once you have arrived at a common ground of what they want, you can share what you want, and work towards a deal that’s a win-win.
Trades are not zero sum
Yes, you want to find deals that are win-win. Win-win means you and one other team got better, while the whole rest of the league did not. And if you make a win-win trade with every team in the league, that’s a dozen wins for you and only one win for each other team.
Additionally, value does not exist in a vacuum. Value is relative to each team’s unique situation. Therefore trades should not be evaluated in a vacuum. Here’s a whole list of reasons a player might be more or less valuable to different teams:
Positional strength or lack of strength
Ranking in the standings
Ranking in individual scoring categories
Keeper viability
Team goals within keeper league competitive windows
Differing capabilities of finding waiver wire value
Different amounts of FAAB remaining or waiver wire priority
Salary cap concerns
Something that’s worth a little to you could be worth a lot to someone else, and vice versa. Find those pockets of asymmetric value and design trades around them, seeking to help other teams.
Be an open book
I’ve interacted with way too many owners who try to hide how much they value players or who they’re actually interested in. They bait and switch, force you to put an offer on the table (and then make fun of that offer), or speak in vague terms. If you want to make a trade, communicate with as many specifics as possible. Share how you value your own players and how you value the other teams’ players. Share what your trade goals are, how you’re trying to improve, and how you think you can help the other team improve. In addition to being a friendlier experience, this approach provides a lot more opportunity for a potential trade partner to grab on to something they’re interested in.
I will often provide other teams a big list of players on both our teams, sorted by how I value them, either in tiers or with dollar values or draft rounds or keeper value. You could also just provide a subset of players if you’re only talking about pitchers or lost-cost players. An example:
“It looks like you have a really strong offense but could use some pitching. If you agree, here’s how I value our players who could be part of a win-win trade. Do you value any of my players more than I do, or value any of your pitchers less than I do? If so, that might be a good starting point for a trade conversation.”
To make this easier, I like to take my auction/draft spreadsheet and re-organize the columns to contain the relevant information and then filter to my team and the other team. Just screenshot and send it along. But you could also just use that as a starting point and then re-jigger the order and/or values. Or start from scratch and type broader tiers in an email. I would highly suggest erring on the side of more detail/granularity, though.
Be aware of Type II errors
We tend to focus on not making bad trades, but not making trades that would have been good for us is just as damning. Not making a trade because it’s too small of an advantage for your team is a missed opportunity. Not making a trade because you’re worried about the other team getting better is a missed opportunity. Not making a trade because you didn’t reach out or forgot to respond to an email is a missed opportunity.
I wrote above about focusing on other teams and other teams’ players. This has the side benefit of removing the bias we all naturally have for “our guys”. We know every reason our guys will maintain their high production or can improve in the future. We don’t as readily see those traits in players on other teams, but we should. We also need to better appreciate the downsides of our guys. This overrating of our guys vs other teams’ players is a big factor that leads to missed trade opportunities. Put effort into plugging that leak.
Other reasons we don’t make trades that would be beneficial include:
Over-valuing downside risk. Yes, you might “lose” a trade. Stuff happens. But the more trades you make with probably incremental advantages, the more you’ll offset those unlucky breaks (and don’t discount the big lucky breaks.)
Being afraid of not reaching a deal. Most conversations won’t lead anywhere. That’s fine. Don’t stop casting your net.
Not recognizing creative ways to gain value.
Not recognizing creative ways the other teams could gain value.
Pissing off other owners so they won’t talk with you.
Communicating inconsistently, both too much or too little.
Expecting a trade immediately. It often takes a while to find the right deal. Maybe you agree on parts of a deal, but need something to change later in the season for it all to come together. Maybe the other team just needs time to emotionally process the trade. Don’t stop checking in (but don’t be annoying.)
How to play in leagues with more trading
If you’re certain the lack of trading isn’t your own fault, and you want to play in leagues with owners who are more open to trading, here are some ideas:
Join a new league. Obvious but perhaps the easiest. Make sure to ask owners in the new league if trading is prominent, or go start your own league, only accepting owners who can prove they are active in trade talks.
Change owners in your league. This can be rough, but if some owners not only don’t talk trades, they don’t do anything at all, perhaps they should be replaced. (And if they aren’t participating, they might be relieved to be allowed to leave.)
Change the league rules to motivate trading.
One, you could reward trades, perhaps giving $5 in FAAB the first time a trade is executed between two specific teams each season. Or set next year’s pick order based on most trades executed. Or give an extra keeper slot to any team that makes at least three trades.
Two, you could change the league settings to include more resources that can be traded. Change from a points league to a roto league, so that 10 categories of different things now have value. Or change the categories so they correlate to each other less. Or switch to an auction from draft. Or make bench slots and keeper slots and FAAB tradeable. Or allow the trading of statistics. Get wild. Invent new resources that have trade value.
Three, add more owners or players. More owners, more owners to trade with. More players, more players that could be traded. (I do find deeper leagues lead to more trades, as the waiver wire contains less and less value.)
Invite me into your league. I like to trade, especially in leagues with unique rules resources, and scoring systems that motivate trading.