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In one of the first fantasy leagues I ever joined, for years the trade deadline was Aug. 1. This is an AL-only league, so the Aug. 1 date gave fantasy managers 24 hours to try and fill any holes created by trades to the National League. This gives away how old the league is. -Only leagues are becoming a thing of the past, and the ones that do exist have mostly switched to permitting players traded to the “other” league to remain on a team’s roster until the end of the regular season.

Most of the leagues I play in now have a trade deadline in late August or early September. In a typical keeper league, nearly everyone already has decided if they are in or out for 2017. But unless your season is going perfectly, you probably are going to need to make some free-agent pickups or trades down the stretch in order to win. This advice is not limited to teams in contention. If you have already given up on your season the last thing you want to do is let your team lie fallow and miss potential keepers for 2018 and beyond.

Below is a brief list of what I try to do in leagues in both situations. While there are occasional gray areas, this article is not intended to address whether you should try to win this year or not (this decision should have been made at least a month ago) but rather tactics for the last two months of the regular season. This is not intended as a comprehensive strategy document but rather a rudimentary outline and perhaps the beginning of a conversation.

IF YOU’RE PLAYING FOR THIS YEAR
Above all else, the first question to ask yourself is what are my realistic odds of winning? Trading four great freezes to finish in third place instead of sixth might win you a little money but it won’t put your name on the trophy. This is the goal in March; this also should be the goal in October. If you are going to tear your team apart in 2018, make sure you have a realistic chance of winning.

My rule-of-thumb when trading with a non-contender is that I refuse to lose out in any category. For example, if I have a cheap Aaron Judge, in addition to the gains I want to make in steals and/or pitching, at a minimum I must replace the power I am giving up. In redraft leagues, nearly every trade you make requires you to give up something in a category to gain somewhere else. In keeper leagues, this does not apply. You must be as certain as possible you are getting more present value back than your opponents are. In keeper formats, this is the ballgame.

Providing consistent analysis/advice on this subject is tricky because every league values future considerations differently. In general, when I try to put together a deal I consider all of the following factors:

1) I’m not going to give up as much in July or August as I would have in May

This seems intuitive but too often I have seen a fantasy manager make the same trade in August that he or she would have in May. 40-60 games of a player will not help your team as much as 100-110 games. On the other hand…

2) It is much easier to know which categories you need in the second half

When I make a “dump trade” in May, I don’t specifically target a category because so much can happen to torpedo my best laid plans. In August, it is easier to address a category deficiency and directly target it in trade. This works in the other direction as well. I might decide not to focus on a category based on the cost and what is available. Blindly trading for “value” makes less sense as the season progresses.

3) Know your trading partners

Your ideal targets are fantasy managers who will give up anything and everything for future talent. It is not enough to look at what your needs are and assume that the 4-6 teams that are out of the race will treat your wares the same way. You must know who will be more receptive to your offers and who will not. This planning should not only impact your trades but how you tackle your FAAB spending and/or waiver wire additions. If the two people most inclined to trade for your cheap Rafael Devers don’t have saves to trade—and you need saves—you had better put some FAAB aside for a closer or devise a path to victory that doesn’t include saves.

4) Hitting prospects generally have more market value in keeper/non-dynasty leagues

This only applies to keeper leagues with a contract clock. Two or three years of major league service is usually not enough time to make an informed decision on a pitcher contract, yet this is often the decision point. If your future value is centered around young arms, expect to obtain less back in trade and plan accordingly.

IF YOU’RE PLAYING FOR THE FUTURE

The biggest mistake you can make is an obvious one, but I’ve seen too many people make it. Never stop paying attention. It sounds intuitive, but the difference between jumping back into contention a year or two after bailing and getting mired in a three or four-year cycle of failure. This applies not only to moves you might make but also to the future value of players on your team. Prospect value changes far more than the value of major leaguers, and if you stop following what is happening in the minor leagues, you could get fleeced. Fortunately, everyone reading this is a Baseball Prospectus subscriber, and has access to the best and most comprehensive prospect coverage there is (/end plug).

Beyond this, there are a few basic guidelines I tend to follow.

1) Don’t make move for the sake of making moves

This sounds like the opposite of my cardinal rule above. But paying attention isn’t synonymous with useless activity. Trading one marginal freeze for another marginal freeze is a waste of time. Don’t waste FAAB resources or waiver priority on a player who has either no trade value or future utility.

A common mistake in this area is trying to plan your March freeze list in August. The inclination for many is to look at a team that has a lot of pitching-heavy value and flip a pitcher for a hitter. But unless you are getting a superior freeze back, don’t bother. Too much can happen between now and March, and unless your league doesn’t trade at all in the winter, you should be able to address your team’s needs in the offseason.

2) Look for contenders’ weaknesses. Don’t be reactive.

Some non-contenders wait for contenders to approach them with trades, thinking that the contenders are so hungry to win that they can sit back, let the offers roll in, and profit ($$$). I guarantee you will make some trades, but I am almost certain you will limit your rate of return. Sending a group email to your entire league is OK. Sending individual messages to each contender is ideal. Look for dead spots on their roster and places where you can provide upgrades. This is where you can clean up if you are aggressive, particularly in deeper leagues.

3) Get rid of all expiring contracts

There are no qualifying offers in fantasy (if there are, please don’t tell me about them in the comments). You do want to maximize your return, but if you have a player whose contract status is expiring at the end of the season, you want to move him. Don’t get hung up on your return or play chicken with these players. Anything you can get back in trade is a win. Don’t be afraid to cut these players after your trade deadline passes. Can they help someone else win your league? Yes, but that’s not your problem. Even a long shot you can keep in the winter is better than a player who you will lose in late September.

4) Don’t trade major-league freezes for minor-league futures

I’m not talking about trading Gleybar Torres for a slightly above-average major-league freeze. But if you have a $20 Mookie Betts in hand, it isn’t a good idea to move your $20 Mookie Betts for two or three mid-tier minor leaguers hoping that one of them will pay off. Perhaps one will turn into the next Torres or Betts, but it is far more likely that all of your lottery tickets will not pan out.

In general, try to acquire volume and potential freezes using free agency and by trading your borderline players this year. Don’t use your best freezes to try and obtain volume. As mentioned above, too much can happen between now and next March to those marginal freezes to make them worthless.

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Nacho999
7/27
Sage advice all around. I've been in an AL only keeper league for 30 years. 5 of us are original and 8 of us have been playing 25 years or more. We all know each other's tricks and histories, but to me the most important things listed above are paying attention even when you are losing, maximize the value of every single roster spot, know the value of minor leaguers and always pay attention to what the other team needs, not what you want. These all seem like no brainers, but year after year some players tune out, make the same mistakes, fall in love with the wrong players and wait too long to unload. The blurb about the receiving team perceiving more value in May than August is so true. I like to make a list of five players I think could rocket forward in value and target them BEFORE they get a ton of press or go 2-4 in their debut. Trying to predict the future, which is what this game is in a nutshell, can be extremely frustrating, never mind injuries. Your roster needs to be loaded with upwardly mobile talent at all times. Absolutely no dead weight. You still may not win, but you'll be a constant threat and well respected by your fellow owners.
cedis81
7/28
Really enjoy the prospect coverage here. For me, it's been reading the daily MLU, and some scouting reports that pop up here and there. Is there anything else I should be checking? That was how I ended up with Victor Robles, but I was equally likely to miss out on him if I didn't happen to remember his name from MLU randomly. Also, is there a better way to monitor a prospect's progress? I ask more for a type of heat index for prospects that have helium. Or, perhaps, a type of list that aggregates a number of times a prospect is mentioned? The Stash List is more for current year, and the minors have so many players that I don't even know 15% of the players in the MLU. Finally, I've found the most helpful part of the prospect coverage is when the report on each player includes swing and miss in their game. That has helped me identify the higher ceiling players that have lower floors. Thanks, as always for you and your teams work!