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How to Orchestrate a Three-Team Trade (Fantasy Baseball)

by Michael Waterloo | @MichaelWaterloo | Featured Writer
May 30, 2020

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“Sorry, I just don’t think this is a good fit.”

No, you’re not getting dumped, your trade offer is getting rejected. Try as you may, you just might not match up well for a trade with a manager for a player that you’re after.

We’ve all been there, right? We stare at a player that we want on our team, but we struggle to find the right piece to send back. It’s not because we want to low-ball them, but it’s we just can’t meet the statistical or positional needs of the other manager.

But instead of tabling the deal, why not think outside the box and put yourself into the shoes of a real general manager. Yup, that’s right (as you probably knew by the title). We’re talking about a three-team deal. We’ve seen them many times in real sports, but there’s a place for these types of deals in fantasy sports, too.

Some platforms, such as Fantrax, give you the ability to make a multi-team deal, and that takes away some of the headache. However, more traditional platforms like ESPN and Yahoo don’t let you make three-way deals directly — you’ll have to take the extra step of letting the first trade process before you can propose the second.

While three-team deals sound fun, they can also be intimidating to approach. Here are some tips to orchestrating the perfect three-team deal.

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Build a rapport

As should be the case with any trades — multi-team or not — you should try to build a rapport with your league-mates. Look, we all want to win, but remember that this is fun more than anything, and having a good relationship with the other managers in your league is important for an enjoyable experience. 

If you consistently give low-ball offers to managers for trade assets, chances are you’re going to run out of trade partners and, in turn, find it hard to even start the talks on a three-team trade.

The same goes for how you respond to trade offers. If someone wants to offer you a pretty bad deal, it’s just as easy to hit reject and say “no thank you,” as it is to cuss them out.

Having positive relationships in your league makes it easier to set up a group chat and get the wheels turning.

Know the needs

You’re in this position because a trade didn’t align with the team who has the player that you want, so get ready to take some PTO from work, lock yourself in a room, and dig in deep to all rosters at play. 

You know that you, Team A, want a player from Team B. But Team B needs an asset that you just don’t have. So you need to find a Team C that not only has that asset, but is also able to stomach losing it.

Believe it or not, that’s the easy part. You now have to see what Team C’s weakness is to see if you or Team B can fill it.

If it’s you, it can be a pretty standard deal. You get the player that you want from Team B, Team B gets the player they need from Team C, and you give Team C the player they want.

But if it’s Team B, it can get a little more complicated. If Team B has what Team C wants, why do they need you?

Well, then it becomes both a multi-team trade and a multi-player deal. In this case, you’re going to have to overpay a little bit to get the deal done. If it’s a paper loss, so be it. Get your guy, even if you have to give an extra prospect or extra player to get it done. 

Cut to the chase and start a group chat, but bring up the idea to both managers first to see if they are open to it. Don’t be coy with them — just come out and say the player that you’re after and see what both teams would need to get the deal done.

Be more flexible

You may have to overpay a bit to seal the deal, as we mentioned earlier. For some reason, when you throw an extra team in there, there’s more hesitation to get the deal done. The managers really need to be convinced that this is the way to go, so if they ask for a B-level prospect, you need to be willing to give in. Are you really going to let someone like Jordyn Adams hold up a deal and stop you from getting the player you really want?

Be patient

I’ve made four three-team deals in my fantasy baseball career. Three were done via a text thread, and one was done as our forefathers intended — at the mini-golf course. In the text threads, all three took anywhere from three days to one week to finally complete, as there were back-and-forth negotiations, and each manager needed time to fully break down the deal. For the in-person trade talks, there were initial discussions made to see which categories we needed help with, and we decided that we would talk over the deal over 18 holes. We reached an agreement by the end of the round.

These deals don’t happen overnight, so along with being flexible with who you will and won’t include in a deal, you need to be flexible with your time, too.

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Michael Waterloo is a featured writer at FantasyPros. For more from Michael, check out his archive and follow him @MichaelWaterloo.

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