One of the hardest things to do in fantasy sports, or for that matter in sports in general, is to give up on a season and play for the future. It runs counter-intuitive to our competitive instincts, not to mention the natural human desire for more immediate gratification. Even so, a well-conceived and executed short-term sacrifice can lead to a far more satisfying run of success in the long term. The team than can identify where it is in the success cycle and act quickly in response is likely to profit from its actions. The Arizona Diamondbacks established and executed a fantastic long-term plan, and now appear to be reaping the benefits. You too can do the same in your keeper league. Here are a few tips on when to go that route, and what to do once you’ve made the decision to dump.

1. Continually Evaluate Your Team. A good fantasy owner should constantly evaluate his or her roster and figure out his strengths and weaknesses, look at what’s responsible for his spot in the standings, and continually keep in mind how all of that fits into a long-term plan. Are you riding the BABIP-express into first place, or did you have a strong team to begin with? If you used a draft tool, how did your team grade out using its projected standings feature? If you are down towards the bottom of your standings, is it because you’ve had some unlucky slow starters, like Robinson Cano, Ryan Howard, and Justin Verlander? Have you had any major injuries, like Troy Tulowitzki‘s torn tendon in his quadriceps? Or is it because your team has fundamental flaws, and is just playing to its level? If it’s due to significant long-term injuries, or just because your team wasn’t projected to win this year, it’s not too early to start planning for the future.

Sometimes this can be easy. I took over a struggling team in a Scoresheet league (BL_Murphy, home of sharks like Gary Huckaby, Rob Miller, Brian Dewberry-Jones, and many other awesome Scoresheet players), knowing full well that my squad was going to have a hard time competing. Even with it being a “soft-eight” league in terms of the keeper cap, my set of keepers was decidedly inferior to many if not most of the teams in the league. So I went into the draft planning to err on the side of youth and upside with every pick, knowing that it would leave me short on innings pitched and at-bats compared to the vast majority of the league. It’s worked about as I had expected. Early picks like Yunel Escobar, Aaron Hill, and Casey Kotchman have worked out pretty well, and there’s a pretty good chance all three will be keeper-worthy next year. I have some good prospects, and hopefully at least one if not two will take that Jay Bruce-like leap that will make them a surefire keeper heading into next year. On the other hand, some other early picks, like Josh Fields, haven’t worked out at all, and I’ve left myself dangerously short in playing time at third base and on the mound. My team is only three games out in my division, but is also just 10-15, and I’ve already needed 43 innings thrown by the dreaded “Pitcher, AAA” and 151 at-bats from the position player equivalent. It’s not a team built to win this year, and any time that I can trade to improve my chances for next year, I need to do it.

2. Be Proactive. Quite often losing teams make two mistakes when playing for the future. They wait too long, and they wait for teams to approach them with trade offers. The benefits for a contending team to act early in the dump trade market are fairly obvious: the earlier they have that stud player on their squad, the better off they are. You should be able to exploit that in trade discussions. In fact, if you have a stud player that’s on an expiring contract and you have to trade him, now is really the time to do that. But don’t just wait for the contenders in your league to approach you. Announcing that you’re dumping to the rest of the league is a decent step to take, but you need to go further than that. The most important thing that you need to do is to identify what type of players best fit your roster, and then go find the perfect fit among your putative trading partners.

There’s a school of thought out there that says it’s best not to be the one to make the first offer, but I’ve generally found the opposite approach works better. If I’m the one initiating trade talks and making that first offer, I have more control over the process. Sure, many times the other owner will counter-offer a trade that brings less value, but that’s all part of the negotiating process. Your initial offer should leave yourself somewhere to go anyhow, while preserving the critical player that you want to get in that deal. Remember that these other teams need to get your current assets almost as badly as you need to find good keepers. The earlier that these trade talks happen, the more leverage you should have.

3. Fit Your League’s Parameters. This tip is seemingly simple, but there are many different keeper league structures, and that has to dictate your trade strategy. One big key is the number of keepers. I play in one hockey league that lets you keep just three players, so more often than not you’re looking to keep the players who can best help you now and not the ones with future upside. If you’re in a baseball league equivalent, you need to be willing to trade away a lot of depth to pick up that one surefire keeper. If you already have your keepers and find that it’ll be too difficult to upgrade, the alternate route is to trade everything that’s not nailed down for draft picks, or auction dollars, if that is allowed.

Other leagues allow you to keep more players, and offer greater flexibility regarding how to rebuild. Even here, look at those league rules carefully. Some leagues, like the RotoWire Staff League, have separate spots for minor leaguers, whom you can keep at no cost except for a minor league slot. Others, like the Murphy Scoresheet league referenced above, have no such minor league protection slots at all. Prospects still have value in that league, but usually only the elite among those prospects, and how soon a player can contribute will be a bigger factor in your decision to target that prospect.

I did recently trade for a prospect in Murphy. Once David DeJesus returned from his injury, he got off to a hot start for the Royals. As much as I like DeJesus for Scoresheet–he’s a very good defensive center fielder and gets on base at a pretty good clip–I also don’t see him as a keeper in this format. A team that needed a center fielder and was positioned to contend this year approached me to ask about DeJesus, and knew that I liked Matt Wieters. We first discussed a larger deal that might have also included Manny Ramirez, but there wasn’t a fit there. I decided that Wieters had enough potential to advance quickly and eventually arise among the elite catchers–that trade is enough for me to protect him next season. That puts me at or near the eight keeper limit, assuming one of the other prospects that I drafted rises to keeper-level quality.

4. Stay Active Afterwards. Even after you identify and trade for your keeper targets, your work isn’t done. Stay active throughout the course of the season, and constantly look for ways to improve your team. That can be done on the waiver wire–you’ll be surprised how often that good, keepable players will get dropped after they struggle, or an injured premier player like Tulowitzki becomes available. Other prospects that were previously off the league’s radar will emerge. Any successful free agent grab can be converted into future value, either as part of a package in a trade upgrade, or as future picks or auction dollars. You’ll be surprised by how much you can improve if you only pay attention.

These tips can help you get started on rebuilding your own dynasty. If you’d like to hear more about this topic, Chris Liss and I discussed the pros and cons and the frustrations of trading early in the season on his show on XM Channel 144. We’ve excerpted that segment in podcast form. Good luck on the trade market!

Jeff Erickson is the Senior Editor at RotoWire, and the host of XM Radio’s Fantasy Focus. He can be reached here.

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