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Flags Fly Forever. Hey, that’s the name of the podcast I co-host weekly with Bret Sayre and producer George Bissell. So I know a thing or two about going for it at all costs, decimating my team’s future in pursuit of a title, and sacrificing the potential plum of back-to-back championships in favor of a “certain” win this year. As a rule of thumb, this is sage advice. If you are on the fence about a trade in a keeper or dynasty league because you are worried you are giving up too much value, odds are good that you should make the trade immediately and worry about 2017 and beyond later.

Yet there are cases where you can go too far and sacrifice too much future in exchange for the present. This seems to fly in the face of the advice that every fantasy expert has ever dispensed. But there are cases where it can happen.

Imagine that you have Byron Buxton in your league at an affordable salary with a contract that will allow you to keep him through 2017 before you have to extend him and increase his salary. Your team is in fourth place with a realistic chance at first place. The person in eleventh place has decided to throw in the towel for 2016 and sends you this email.

Hey Joe (your name is Joe in this scenario, deal with it), I’m a big fan of Byron Buxton’s potential, so I’m offering a private sale on Mike Trout. I will trade him to you straight up for Buxton. I sent an offer through the site, just hit accept if you want to do it.

This is the kind of deal I see a number of experts recommend accepting without hesitation. “We don’t know what Buxton will look like at his peak, but we know what Trout is now. You know what Trout will do to help you win this year. You don’t know what Buxton will do. Flags Fly Forever.”

Intuitively, all of this makes sense. What this advice neglects is what Buxton’s market value is in your particular league.

Imagine for a moment you had a choice between the following two trades:

  • Trade A: Gain 15 home runs, gain 60 RBI, gain 10 steals, gain 50 runs.
  • Trade B: Gain 25 home runs, gain 90 RBI, gain 15 steals, gain 80 runs.

It is fairly obvious that you would take Trade B every time. Yet the advice above assumes that you should trade Buxton for Trout regardless of what the market in your league has to bear. To be fair to the experts out there who answer fantasy questions, they typically have little if any context, don’t know what the questioner’s league is like, and likely play in expert leagues that are redraft leagues only. (also, many of them answer questions for free out of the goodness of their hearts. So be nice.)

The best person to answer whether or not Buxton for Trout is a good deal in your league is you. If you have played in your keeper league for long enough, you probably know the answer and don’t need my help. Thanks for reading and have a pleasant rest of your day! But if you still aren’t sure, here are some basic questions you should ask yourself before making a trade.

What Is the Trading Culture in Your League Like?
Is it a “dump/bail” league, a league with mostly straight trades, or some kind of combination of the two? The answer to this question will give you an idea of how much value is placed on players like Buxton. The question obviously isn’t “is Byron Buxton better than Mike Trout at this moment?” but rather “what can I get for Byron Buxton in my league at this moment?” In some leagues, the answer to that question is Mike Trout. In other leagues, the market price is Mike Trout and Danny Salazar. If you are new to a keeper league, try to go through past seasons on your league’s website to see what past dump trades netted their owners. If your league’s website doesn’t offer this capability, watch to see how this year’s market coalesces.

Who Are the “Actors” in This Year’s Trade Market?
In Major League Baseball, we hear frequently about a team’s institutional history when it comes to buying or selling at the trade deadline. The Reds are likely to sell at the deadline simply based on their won-loss record. The Yankees are far less likely to sell based on their historical track record as a winner and because it might tarnish their brand. Fantasy baseball doesn’t have to worry about fans and catering to institutional memory, but this doesn’t mean that organizational philosophies do not exist.

There are too many different personality types to cover within the space of this article, but below are four general kinds of personalities you may see in a keeper league.

  • Loves the Future – These fantasy managers always seem to be rebuilding and chasing a future that never comes because they are always rebuilding and chasing the future. If they’re not going for it this year and you have Yoan Moncada, congratulations on your imminent jackpot.
  • Almost Never Gives Up – This fantasy manager almost always goes for it, even if his or her team isn’t that good. Finishing third and collecting moderate prize winnings is preferable to giving up and finishing ninth, even if that improves the team’s chances in the future.
  • Can Go Either Way – These types don’t necessarily have a strict philosophy and tend to go where their guts take them.
  • Barely Trades – This fantasy manager almost never makes any kind of trade at all. He or she also tends to disappear during the years when his or her team slips into the second division.

In keeper leagues, how much action there is going to be in the trade market depends a great deal on the types of personalities you will be dealing with during the season. If three of the bottom four teams in your league tend to put a heavy emphasis on the future, it is likely that there will be lot of bail trades early in the season. On the other hand, if three of the four teams at the bottom are of the almost-never-give-up variety, you will need to consider making this-year-for-this-year deals and being more creative.

What Do the Standings Look Like?
By mid-June, it is usually fairly clear if it is going to be a season when one or two teams dominate, three to five teams are in tight competition for first place, or if there is a big clump of teams in the standings from top to bottom with minimal or moderate differentiation. In a season where one or two teams are dominating, the possibility of multiple teams throwing in the towel is significantly higher than in a year when there is a large scrum of teams that believe a victory this season is achievable.

There is another component to this portion of the analysis, and it is the most important one of all. Can you win your fantasy league? Not every sixth, fourth, or second place team is alike. A weak third place team should either stand pat or perhaps throw in the towel and play for next season. A sixth place team with a solid baseline should at least examine the possibility of playing for this year. Elements like fantasy contracts and salaries also tie into this type of analysis, but the general idea is that there isn’t a right or wrong answer.

The Takeaway(s)
Even the most basic fantasy player knows that, statistically speaking, Trout is better than Buxton. The real question isn’t which player is better than the other one but what is the market value of Byron Buxton in your specific league. You are not competing against me or any of the experts you are querying about your fantasy team. Your template for the best deal should not be “am I getting more value?” but “am I getting as much value as I possibly can?”

Last year in my home league, I threw in the towel despite having a fifth-place team in what appeared to be a tight clump of teams. A closer look at the standings revealed that the top three teams had stronger rosters and that I would have needed a minor miracle to win. As a result, I kept together a strong core, drafted well this past spring, and am currently in a good position to compete this year.

This decision also allowed me to make a bail trade this year that I would not have made last year. Flipping a cost controlled Mookie Betts wasn’t ideal, but given my solid position overall along with a couple of holes I had on offense I was willing to move the superstar outfielder for three non-superstars but productive everyday players. In 2015, flipping Betts in a quixotic effort to finish in third place made little sense. In 2016, moving Betts to solidify what appears to be a strong team is eminently logical.

Contextual decision making is a difficult topic on which to offer advice. It is even more difficult because the market value of undervalued players in every league is different. Mastering your league and not only how your peers value cheap, young players but also understanding the market during a given year or even during a specific week or month in-season can go a long way to pushing your team toward a win in leagues that permit imbalanced trading.

Thank you for reading

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