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Just taking a page from your book, Doc -- and visiting Opposite-Land.  :)
I understand the reality that I'm likely to be walking the plank alone on this one. 
But, as I noted above, while I think I'm getting a decent handle on how Z is viewing most of these trades - I also note that so far, Z's reads on pitching talent have been ... wanting.
All three of your least favorite Z-trades have involved pitchers.  He seems to be fishing for "pitchers" rather than throwers, (in general terms).  But, I'm thinking ORDER is in play here.  The Morrow/Jackson rumors were all BEFORE the Lee trade.  I'm thinking he didn't pull the trigger on the Detroit deal ... not so much based on talent or prospect differences, but because he got a call from Toronto and/or Philly AFTER the Morrow/Jackson trade rumors started heating up. 
I said before the Lee deal that the club (for '09) needed a TOR and a BOR guy.  If Jackson was the opening sequence for TOR acquisition, CLEARLY that gets dumped overboard immediately when you're looking at Lee instead.  My intuition says that the more likely scenario (despite the rumors) was that it was going to be Morrow+ for Jackson, (as typically starters are valued more highly than relievers, and THUS FAR, Morrow just doesn't have the SP rep to warrant him being "overly" valued as an immediate starter.  (A plus prospect or project ... sure, but not a true SP).
Having snagged Lee, I could see Z looking at the landscape and wanting to shore up the biggest problem with the club at the moment - the bullpen.  Not a popular opinion, but I was waxing negative on the pen all through 2009, but most of the reality of how poor the pen was behind Aardsma and Lowe was lost in the giddiness of the winning season.
Having done some serious prospect dumping, Z needed to swing something to bring immediate help PLUS some farm food.  The Jackson option was removed by the time the Lee deal was done.  If Z sees a "bunch" of cheap BOR options to go with the Felix, Lee, Snell, RRS quartet -- then go ahead and shore up the pen with a guy satisfied with the pen who would be THRILLED with a chance to start some day, instead of a guy that either was never a true prospect - or who the previous regime had damaged beyond repair before Z arrived.
But, yeah, if Detroit REALLY was offering Jackson+ for Morrow, then your argument of Morrow's market value carries weight.  Honestly, I was never high on Morrow OR Jackson, (though Jackson in many ways is the SP version of League on several levels). 
Probably the biggest difference between me and most of the blog-o-sphere is that I value CONSISTENCY in pitching far, far more than dominance.  Smoltz was twice as dominant as Maddux.  Maddux was twice as good, (until Smoltz eventually learned consistency).  Wash showed what a barely above average pitcher who is CONSISTENT can do during 2009.  I'd rather have RRS pitching "well" 80% of the time than Morrow pitching "fantastic" 10% of the time.  (hyperbole, but you get my drift).