Fantasy Strategy: When should keeper-league owners pack it in?

One of the more difficult decisions to make for those in keeper leagues is deciding that it is time to pack it in and look towards the future. But that's what a keeper league is all about. The rules are designed for the contenders to sacrifice some of their keeper foundation, weakening them down the line in exchange for a run or the roses this season. On the flip-side, keeper leagues allow struggling teams to rebuild, enhancing their chances to be in the business end of a similar trade next season, where they are fortifying their own championship efforts. Today we will focus upon some principles involved in the art of the so-called dump trade from the point of view of the rebuilding squad. Next week we will look at things from the perspective of the competing owner.

The dump trade is the industry lexicon for a deal that strengthens one team this year and the other team in ensuing seasons. The team attempting to challenge for the title acquires players with greater potential for this season while the rebuilding team acquires players at a better keeper value. The difference in raw performance value this season is compensated for via better bang next season and beyond.

If you are in rebuilding mode, your primary concern should be for your own squad. If you make a deal that helps the team already in first, or a team run by someone you are closer with than you are other league members, so long as the deal is indeed the one that helps you the most, pull the trigger with no guilt or regrets. You may want to do something to remove as much ill-perception as possible such as publicly advertising your desire to dump along with listing your available players. But if you make a deal that best aids your team that is what counts. However, it is often better from a strategic sense to spread the wealth a bit and not consummate an all-of-mine for all-of-yours swap, but the reason should be to maximize your return, not to attempt to disrupt the competitive balance as little as possible. It is incumbent upon the other teams challenging for the championship to follow suit and deal away some of their keepers. If they do not agree, they should join a redraft league or a dynasty format where the dump trade is not part of the league dynamic.

Secondly, if you are dumping, dump everything -- don't hold back. One of the more common errors keeper owners make is to attempt to compete but not to deal away all your keepers, only some of them. What usually happens is you end up falling short this season, and go into next season with a weaker keeper list than those that sold out completely, setting yourself for a second straight season of mediocrity.

That said, one of the best ploys is to hold back some of your keepers for the end of dumping season. Dump trading is driven by supply and demand economics. When you are dealing with current value versus future value, there is no algorithm that can be employed to gauge equity. Fairness is simply what the market will bear. The supply of available keepers and their demand versus the supply of available present day talent and their demand dictates the going rate. At the extreme, if there is one decent keeper available, that team can hold out for the best package of present day talent, even if the total value is more than someone else received for a lesser keeper. Throw precedent out the window, supply and demand economics drive dump trading. Going back to the point about holding some of your talent until the end, inevitably there is one team that is reluctant to part with a jewel of their foundation. But eventually, they will conclude that they need to deal him to complete their efforts and you want to have the ammunition to be in on the deal.

Something to keep in mind when deciding who to deal away is that keeping salary is not always a bad thing. That is, the best keeper list is not always composed of a slew of really cheap players. Remember, in keeper auction, the best players are always purchased for inflated prices, as there is more money to spend than there is available talent, as the keepers are frozen under value. As such, if you have $200 of your $260 to spend next spring, you are not likely to buy $200 worth of talent. By the end of the auction, players are going at value or under, but before that, inflation dictates paying more than "value". Let's say you keep $120 worth of players for $60, leaving you $200. You then buy $50 worth of talent with your last $50, but only buy $100 worth of talent with the other $150. For your $260, you have $270 worth of talent, effectively giving back $50 of the $60 profit you took into the auction. Now let's say you protect $230 worth of talent for $210, only a $20 profit. But with your $50, you also buy $50 worth of talent like above. You have $280 worth of players as compared to the $270 generated by the owner with the keeper list replete with cheaper players. This is just something to keep in mind, but the numbers presented here are not exaggerated to make a point -- they are quite representative of what occurs in many keeper leagues.

Now let us shift our focus to the types of players that make the best keepers. Obviously everything is contextual to your league, but here are some generalities to help construct the optimal set of keepers.

Simply put, hitters make better keepers than pitchers. There are a plethora of reasons, but the most important is come next spring's draft and into the season, there will be more quality pitching available than hitting. That is, either during the auction or via in-season trade, you will be able to acquire the pitching you need to make your championship run; it is just the nature of the player pool year after year. There are two notable exceptions. The first is very cheap, young but established starting pitching, with the key being established. Someone like Jon Lester, Chad Billingsley, Yovani Gallardo or Zack Greinke can be considered to be established. Someone like Clayton Kershaw or Max Scherzer might have potential, and may actually realize it next season, but in order to be a solid keeper, you really want to be protecting more than potential. There will be plenty of potential available in next year's draft. The second exception is present set up men who are all but guaranteed to be closers next season. I know, the rule of thumb is not to pay for saves, but the idea is you are freezing them for an extremely low price. Last year, Jonathan Broxton, Heath Bell and Chad Qualls were virtually assured of being closers this season. But so were Carlos Marmol and Manny Corpas. However, especially in deeper leagues, players like Marmol and Corpas still have value so it is usually not a total waste if they do not get saves.

A global group of players to shoot for are players presently injured for an extended period of time, but in all likelihood will be fine next season, if not later this season. And this year offers a myriad of such entities such as Jose Reyes, Grady Sizemore, Carlos Quentin, Josh Hamilton, Alex Gordon, Conor Jackson and Rickie Weeks, with others sure to follow.

Another general type of player is the post-hype prospect that has not quite performed as expected yet. Remember, just because you deal for a player now, you are not required to protect them next spring, there is nothing wrong with stacking your team with potential keepers and letting the rest of the season play out. Possible targets are Howie Kendrick, Delmon Young, Billy Butler or Chase Headley. These players can probably be upgraded by their present owner and may finally show enough to warrant keeper status next year.

The absolute best keepers are the cheap but established hitters. In most instances, these emanate from leagues that also have a farm or minor league roster so they have a cheap salary since they were drafted as a prospect. Of course, these will cost the most to acquire and will be the most difficult to pry from their lucky owner, but it is trading away players of this ilk that wins championships. Examples of possible studs are Ryan Braun, Evan Longoria, Matt Kemp, Ian Kinsler and Justin Upton.

In summary, embedded in the fabric of keeper leagues is the ability to make deals to enhance your chances to compete in future seasons. Do not be shy about exercising your right to do just that. But as you are planning, target players that will cause you to spend the winter yearning for the spring and draft day. This way, next season, you won't have to read the primer on how to build a keeper list but instead wait for the one detailing how to fortify your squad for its championship ride.