Fantasy 101: Dynasty and Keeper Trading

Travis Sherer breaks down dynasty and keeper league strategies, including "the unadvertised three-way."

I started my first dynasty league at college in 2001 with a bunch of dorm-mates. That league still exists. A year into the league, I remember receiving a trade offer in which I distinctly remember proclaiming loudly: “I wouldn’t have accepted if I was either manager.” Back then, I thought that was because it was a terrible offer. After playing that league for five years, I realized that was because I didn’t know what I was doing.

Do I know what I’m doing almost 20 years later? Probably. There are a few things I wished I knew going into my first (second, and third) dynasty league about trading:


What is Tradeable?


Not every dynasty/keeper league has the same number of tradeable assets. Find out what assets are available to you and test them out. For example, in some leagues, you can trade your waiver-wire position. In some, you can trade salary. Be the one who knows the most about how much these things can be worth and find a way to dictate the market. Go beyond amateur draft picks and prospects.


Prospect/Pick Trade Advice


Never Ask for the Prospect You Want First


Imagine you have two lottery tickets to a drawing that happens tomorrow. I want one of your lottery tickets. I say, “I’ll pay face value for that ticket” and point to Ticket 1. You’re going to say, “No. I want more than face value for that one.” Even though both tickets have the exact same chance to win, because I asked for Ticket 1, it immediately makes you wonder why I want that ticket more than Ticket 2—even though I can’t know more than you do because the drawing hasn’t happened yet and neither one of us can see the future. It also makes you wonder what about Ticket 1 is so special—and since it’s so important to me, I should pay more for it.

However, if I say, “I’ll pay you full price for one of your tickets,” you’ll be more inclined to accept. You don’t know why, but it doesn’t seem like either ticket is as important if I don’t specifically ask for Ticket 1 or Ticket 2. The same can be said about prospects. Make no mistake: All prospects are lottery tickets—some just have more chances to win than others. All of this is to say that asking for a specific prospect is always a mistake—but only if it’s the prospect you really want.

Whenever you ask for a specific prospect, the opposite manager always thinks, “What does he or she know that I don’t?” Even if you have a good explanation for why you want him, which doesn’t include that he’s going to be the second coming of Mookie Betts or Paul Goldschmidt (both unheralded prospects), that won’t matter. Your trading partner is already suspicious, and thus less likely to trade, and the price has already gone up.

That said, there are two ways to avoid inflating your price by making the mistake of being direct and transparent. The first method is to give the other manager a list of prospects you would like and hope he or she responds in the affirmative toward the desired target(s). This method always gets you some information in return because even if you do not get the response you’re looking for, you’ve found out roughly what the price is for all five. However, if you don’t get the answer you are looking for, you are stuck at this point unless…

…Well, unless you use my preferred method of prospect-trade negotiation: the decoy. Ask the manager about a prospect who shares something in common with the prospect you really want (skill set or position usually work best). When the other manager declines a low(ish)-ball offer, you then ask for the real target—implying that you value this player less than the first prospect. It will start the negotiation off at a lower point without offending the other manager.

Note: This strategy generally only works once you get past the absolute top tier of prospects. Asking for the No. 10 shortstop first and then asking for Wander Franco will not work. There needs to be some amount of debate as to who is better because, outside a very few no-doubters, nobody knows which prospects are going to pan out in baseball—or when they will do it. You can watch players all you want and look at advanced stats all you want, you are still going to whiff. The whole point is not to give away who you think is more likely to connect.


Put Picks in Context


Some managers will trade their draft picks because they don’t want to research the upcoming draft. Take advantage of this laziness and buy them—every time. They will always be undervalued. If you are thinking about trading your first-year draft picks, figure out what they are worth to you.

You do this by ranking the draftees and figuring out who you could reasonably expect to get with that pick. Then you put that prospect in context to your top 100 (or 200) prospect rankings. That will give you an idea of what you think a prospect is worth among his peers and among major leaguers. This is a terrific exercise because it will help you in the future, and often times it talks you out of selling your draft picks.


Do Not Intentionally Diversify Your Prospect Talent


I hear it from readers all the time: “I’ve got a strong group of four outfield prospects, so I’m thinking about trading one or two for some infield help.” This is a mistake. Having a surplus of talent at one position is never a bad thing! What managers who think like this are telling me is that they are afraid they will have too many good, young outfielders…

You can always trade good, young players of any position after they have panned out—and for more than you could have gotten for them as prospects. If you really believe you have four outfielders who will become All-Stars, sit on them until it happens. But if only one of them turns out as you hoped, you have a 25 percent chance of trading the good one away for a prospect of a different position who could also not pan out. You’ve essentially weakened a strong position to not really strengthen a weak position.

This doesn’t mean that you should only draft outfielders or some other position. Take the prospects you think will have the best chance of panning out regardless of where they play, but do not trade for (or draft) a third base prospect just because you don’t have one. Always have the best player.


Always Try for One Last Pick


You and another manager have exchanged six offers back-and-forth. You’re close to getting a deal finished. Now is when you ask for one extra pick. Not a first-rounder. Not a second-rounder. You ask for a pick in the last round. You might be thinking that after all that negotiating, why risk blowing up the deal over one pick? Because the other manager will be thinking the same thing, and just say “yes” to get the package they thought was already on their team.

Depending on how many picks your draft contains and who is available, that extra pick can be enormously valuable. It gets you one more chance to win the lottery. Some picks I’ve made in the fifth rounds of drafts have netted me All-Stars or elite closers. It doesn’t happen often, but it does happen. Make sure you’re the one it happens to. Go for the pick.


Major Leaguer Trade Advice


How to Appropriately Value Age


This is the question that is at the heart of trading in dynasty leagues. It shouldn’t come as a surprise that there is no tried-and-true formula for weighing one player’s future worth against another’s. If there were such a formula, everyone in dynasty leagues would use it…and then there would be managers who find a way to exploit it, etc.

When trading, I suggest considering age as another statistic category your team needs to win. Just like home runs, RBI, wins, saves, etc., you should be fighting to keep your age down with every trade you make, regardless of your team’s record. Like any other stat category, a low age alone does not make a player valuable. Instead, it is the combination of a low age and other desirable statistics. The more desirable the statistics, the more valuable the player.


‘Make Me an Offer’


Don’t fall for this. It never fails. Every year, at least one person in your league is going to post something to the effect of how they have Players X, Y, Z, and are looking for A, B, and/or C…”Make Me an Offer.” Do not do the work for him or her. This automatically puts you at a disadvantage. They know you’re interested in something because you’ve come running to the dinner bell—now they can dictate the price.

If somebody puts a request for trade proposals up on the board, they are the one in the weaker position. So do what they are doing back to them. Tell them you’re interested in their Players W, X, Y (always include at least one player they did not put up) and tell them to offer something to you. If you don’t get an offer, you’ll know this was a fishing expedition. If you do get one, you’ll know how serious they are to trade. If it’s a terrible offer, they are just looking to unload crap before they drop it on the wire. If you get a reasonable one, proceed with further talks.


Never Stop Thinking About a Three-way


Not great marital advice, but good for dynasty leagues. Always be talking trade. You don’t even have to be talking specifics. My favorite deal is the unadvertised three-way. Always try to find out as much information as you can about who likes what player. A lot of the time, when there is a player you want on Manager A’s team, you do not have the player(s) that Manager A covets to make a deal. However, Manager B might have that player, and Manager B might like some of the players on your team who you’re ready to deal.

Do not inform Manager B that Manager A would trade. If you do this, they make a trade and you get nothing. Instead, ask them hypothetical questions about players they like. Once you have a good sense, you can get Manager B’s player, have Manager B send the offer, and ask Manager A: “If I could get (Manager B’s player), would you trade me Player X for him?” When he or she says yes, accept Manager B’s offer and you’ve just completed the unadvertised three-way.

Just remember: The art of good business is being a good middle man. Buh bye.

Featured Image by Justin Paradis (@freshmeatcomm on Twitter)

Travis Sherer

All Seattle Mariners fans have learned the future is all we have because the present is always too painful. I am Western Washington University alum, a local sportswriter, an official NCAA basketball statistician, a freelance radio and television production statistician, and a minor league standup comedian. Follow me @ShererTravis on Twitter.

One response to “Fantasy 101: Dynasty and Keeper Trading”

  1. Dave says:

    Timeless tricks of the trade!

Leave a Reply

Your email address will not be published. Required fields are marked *

Account / Login