Posted by Mike Caprio June 1, 2009

Heading into June, 3/4 of my Fantasy Baseball teams are doing surprisingly well.  When it comes to the 4th, I’m not sure whether to “fish or cut bait” on the remainder of the season.

The end of May marked the completion of Week 8—1/3 of the baseball season—and many Keeper League GM’s find themselves looking towards 2010.  

So…the question is:

“When Should You Throw in the Towel on 2009?”

The one thing I love about Keeper Leagues is that there truly is a “next year”…where you can parlay veteran talent into prospects for a brighter tomorrow.   

In my case, this week’s sweep put me at 10-14, hardly the record of a team that has no shot of making the playoffs…but with the division leader at 20-4, I have to consider whether my veterans can yield pillars for my franchise for years to come.

When determining when to “call it a day” on 2009, you should consider the current make-up of your ball-club:

1.) Is your roster constructed like a “win-now” franchise?  

Fantasy rosters are like Major League rosters—some are young, some are old, and some have a nice balance—which one are you?  If you play in a contract league, do you have contracts that will expire in 2010, but those who offer value to someone making a push?  Perfect example would be Todd Helton or maybe even Trevor Hoffman, players you likely would move when looking towards 2010—but those who could offer a contender a nice bump (and back to you real value) in 2009.

2.) Do you have cornerstones with which to build a contender?

When I am constructing (or rebuilding) a roster, I try to identify a cornerstone, or pillars to build around.   In a Keeper League this is especially important, as you have the ability to pick-up players early in their development and grow with them.   What I do is identify my “Top 3″ players at each position and try and acquire one or two of them.  These “Top 3’s” shouldn’t be 35 year old veterans, but should be young up-and-comers you’d be pleased to plug into your lineup everyday for the next 3-5 years.  As I mentioned in my our Keeper League GM Debate with Phil Brody a few weeks back, I made a trade last year that positioned me nicely for the next few years.  In a highly controversial trade at the time, I moved John Lackey and Ben Sheets for Evan Longoria.  At the time I seemed “off my rocker”, but today there is no way I would have been able to pull off that deal…but at the time Longoria was an unproven talent, but one I identified as a “pillar” player in a sell-off and am now reaping the rewards this season.

Once you have identified your franchise type, and your pillars, you should look for trading partners.  This is when the fun begins…using all the tools at your disposal (PECOTA, BABIP, FanGraphs.com, Will Carroll, MiLB.com, etc.) try and determine when one of your pillars is valued lower than he should be, and pounce with an offer that fills the other team’s needs.  

In Roto this is pretty easy, and in PPA leagues it’s usually a positional hole.

In situations like this opportunity can strike with top prospects, especially those who are expected to compete for starts or at-bats when rosters expand or next season….depending on how much your trading partners focuses on the “Farm” could enable you to steal a solid contributor for your ball-club for many years to come.  

Tomorrow I’ll walk you through my thinking related to a 2009 “sell-off” and my targets for rebuilding towards 2010.

In the meantime…when you do you think is the time to “sell-off”?

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