One of the tougher yet most important decisions that both major league and fantasy teams must make is whether to go for a playoff (money) spot or to sacrifice the season and plan for the future. While there are some leagues that penalize teams for finishing in the bottom few spots in their league, more often than not there’s nothing worse than going for it and finishing one or two spots out of the money. Still, the decision to pack it in for this year and plan for the future can bear some tasty fruit. Next week we’ll review some tips for those going for it this year, but today I’d like to focus on teams that are forced to plan for the future.

  1. Deciding when to Fold

    This is a fundamental decision, yet one that hasn’t received much attention over the years. The most common mistake a fantasy owner can make is to wait too long to fold up his tent and play for next year. The consequence of that decision, or lack thereof, is that the top keeper candidates on the contending teams are already spoken for, and you’re left getting much less value for your expensive stars. It’s been my experience that the team that bails first gets the most bang for its buck in dump trades. You’re far better off dumping too early rather than too late.

    So when do you give up the ghost? This is a tougher decision in a categorical league than a head-to-head or points league, and there isn’t a hardfast rule of thumb. In some leagues a last place team still has a legitimate shot at moving up to a money spot, where in other leagues a mid-tier team might be hopeless. It’s a matter of context, but some general factors include the size of the league, the gap you need to make up in key categories and the general health of your team. The RotoWire Staff League is an 18-team mixed league, with eight payout spots (although the final two spots don’t cover the total cost of the buy-in) and penalties for finishing in the bottom five. Generally speaking, if you’re sitting in 16th place by the end of June, it’s possible that you could work your way up to a money spot and out of the penalty, but not likely. Similarly, if you’re sitting at the bottom of all the qualitative categories (in most leagues those are batting average, ERA and WHIP), you’re going to have a hard time making up ground. If you need to make up 16 saves just to gain another point, that’s probably going to require you to trade for not one but two closers just to make a big enough impact there, most likely at a severe cost elsewhere. Finally, if you’ve stocked your roster with the likes of Barry Bonds, Armando Benitez and Clint Barmes, and you’re well out of the money spots, the chances of you adding quality replacements to spark a run seem slim.

    If all three of those criteria apply, and in our league that does to a certain unfortunate soul (we’ll just call him Bret), you should have already started the trading process. For that matter, you should immediately give me a call about finding a new home for your expensive yet attractive assets like Mark Prior and Jim Edmonds.

    In a head-to-head league it’s a lot easier to eyeball your situation and come up with the correct answer. Just remember to be realistic–the Astros capped off a miracle run to not only win the wildcard (I refuse to capitalize it, despite the honor it so deserves) but make it to Game 7 of the NLCS, but such miraculous runs happen entirely too infrequently.

  2. Who to Target

    The next big step is finding your ideal trade targets. The good news is that if you act early, there will be a number of contending teams that you can play off each other to get the best package. The bad news is that even those teams will have few really attractive keeper candidates that aren’t already making a big contribution to that team’s success. You want to go after young players that have, in the words of Hubie Brown, tremendous upside. Most keeper leagues also have a salary component, so cost is also a huge factor. Just make sure that you don’t overrate the cost factor at the expense of talent. You’re far better off trading for a $10 player that has a chance to earn $25 next year than you are a $1 player that could earn $7.

    So you have the general concept down, how about some specifics? Two good starting points include Baseball Prospectus’ Top 50 Prospects list and RotoWire’s R.O.I. (Return on Investment) 100. Try to focus on the elite prospects and first and second-year players. Focus more on overall value and less on your team’s specific positional needs. Even if you have a useful Placido Polanco occupying your second base spot, don’t let that be an obstacle to trading for Rickie Weeks. If all other factors are equal, go after the position player rather than the pitcher. You only get to do this once, and speculating on young players is risky enough, so anything else you can do to remove risk helps.

    It’s important that you find your trade targets and pursue them aggressively. Don’t be afraid to overpay for that premier keeper. Don’t let a $3 Joel Pineiro as a throw-in stand in the way of you making a deal for a $1 Delmon Young. If it requires you giving the extra throw-ins, you have to do it. Just remember the payoff.

    You’re also going to have to keep the league’s specific dumping rules in mind. Many leagues have an in-season salary cap to prevent the most onerous of dump trades (whether those rules are necessary, appropriate or effective is another debate for another day). Be proactive in making sure that your trade fits under those parameters. If you need to take back salary in the deal, find the most effective way to do so for your trade partner. Too many trades are killed off by the extra layer of complexity in the league rules and the unwillingness of one trade party to put the effort in–take that aspect out of the equation. After all, you’re the one who really needs this trade, not him.

    Those of you in keeper leagues that don’t have salaries or draft pick rounds attached, it’s a different animal. While relative age is still an important factor, trying to get a player closer to his peak is more important. This is doubly true if you can only keep a small number of players (approx. 3-5) from year-to-year. In this situation, you’re going to have to offer the classic quantity-for-quality exchange. Again, don’t be afraid of overpaying–it’s important that you get your selected trade target.

  3. Stay Active

    Trading is important, but your work isn’t done once you’ve made your big dump trade or trades. Stay involved on the waiver wire, paying particular heed to when a team calls up a hot prospect. Remember, you’re already playing for next year, so you have absolutely nothing to lose by giving these rookies a shot. This is doubly true in leagues where you can pick up players with FAAB bids and keep them at the price you paid for him in that bidding. Now is the time to speculate–those owners who took the chance on picking up Yhency Brazoban last year or Chad Cordero in 2003 ended up with a free cheap closer that they could keep. Even if they don’t fit your roster’s needs in terms of keepers, they can also give you another trade chit to land that big keeper prospect that you had your eye on.

It’s never fun to throw in the towel, but if you go about it right, you can at least soften the blow for future years. If you’re diligent about the process, you can build the foundation of a future champion.

Jeff Erickson is the senior editor at Rotowire, and the host of XM Radio’s “Fantasy Focus,” heard every weekday at 2 p.m. ET on XM Channel 175. He can be reached here.

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