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Doc asks a fair question -- if you appear to be right in the thick of a pennant race on July 1st, if you don't try to win then, when do you try?
Ultimately, the answer is simple in conception - and massively complex in reality.  You make that move when the COST for that move is not excessive.  The decision of going for it or not is not just about the odds of winning this year -- it is also about the costs and lowered odds of winning in the future.  What are they?
What if the question is phrased this way?  Is it worth it to improve the chance of winning the division this season by 5% -- if the odds of winning 60 games a year for the next 4 years rises by 10%?  I would say everyone who stood up and said - "Yes, the Bedard trade is a good idea, even with the risk," was agreeing to the concept that if the move fails, then I am willing to accept miserable performance for the team for some number of years hereafter.
But I haven't heard anyone stand up and say -- "Well, we went for it in 2008, and failed.  But, it's worth it to me to be an also-ran for the next 6 years, because we were willing to go for it, when it APPEARED that we had the chance."  No, the masses are standing up and once again champing at the bit to "go for it" all over again -- and hand waving away the costs associated with doing so.
You want a big bat.  Bedard can bring a big bat.  (but that doesn't exactly improve the shot at the brass ring, does it?).
When can you make those go for it moves?  *AFTER* you have built an infrastructure of development and depth on your farm that the trading away of prospects is not crippling.  Atlanta was castigated a couple of years ago for trading away Andy Marte - a drool over prospect on nearly everyone's list.  Atlanta didn't act out of desperation -- they acted knowing what else they had on the farm.  Escobar, Prado, Diory Hernandez, etc. 
Z's problems with this decision are exponentially more complex than just to try or not.  The question starts getting hard at "try with WHAT?"  Fans might not be too upset if Clement were dealt at this point -- but a failed audition as a hitter and unable to field ANY position drives his current trade value way down. 
Halman is the #1 prospect for the Ms at this moment, (and having a dreadful season).  Gee, another wonderful sell-low candidate.
You know who the Ms could move to get a big bat?  Someone who really has NOT been critical to their success in 2009?  Brandon Morrow.  There are plenty of teams out there that have reason to believe they can deal with him better than the Ms have.  Of course, once again, we're not talking someone whose trade value is peaking, are we?
Whatever decision is made -- the 4000 pound gorilla is this -- what is the 2010 roster (and beyond) going to look like?  At this point - the only certainties are:
CA - Kenji; 1B-Carp; 2B-Lopez; 3B-????; SS-YuBet; LF-Wlad; CF-FGut; RF; Ichiro; DH-???
SP - Felix; Silva; Vargas; Olson; RRS
The difficulty in figuring out a "go for it" trade are TRIVIAL compared to the complexities involved in attempting to build a winning organization.  Honestly, the optimal way I see for the club to potentially go for it, without severely hurting the future is probably to deal Morrow.  His market value is probably still extremely high -- and he hasn't been integral to the success in 2009.  And, maybe just maybe, Z can swing a Putz-like deal the includes some immediate help AND some future potential as well.