SCOTUS scratches my sentencing itch, but also has me scratching my head

I am, of course, excited that the Supreme Court has now taken up two new federal sentencing cases, Kimbrough from the Fourth Circuit and Gall from the Eighth Circuit, to deal with post-Booker sentencing issues (basics here).  Based on a quick review (and helpful reader comments) and more from SCOTUSblog, it seems that that Gall is a partial replacement for the Claiborne case because it addresses a below-guideline sentence reversed by the Eighth Circuit.  But unlike Claiborne, Gall is not a crack case, so Kimbrough was apparently taken to allow the Justices to address directly whether a district court may deviate from the guidelines based on a disaffinity for the harsh crack guidelines.

Perhaps the key and most significant fact in both Gall and Kimbrough is that the district court in both cases imposed a below-guideline sentence that a circuit court thereafter reversed as unreasonable.  In sharp contrast, the Rita case still pending before SCOTUS (and still expected to be decided this term?) deals with a within-guideline sentence imposed by the district court and affirmed as presumptively reasonable by the Fourth Circuit.  Also significant is that the Supreme Court apparently plans to hear Gall and Kimbrough under a normal schedule next Fall, but likely still will issue a ruling in Rita this month.

So, adding up these pieces, what does this likely mean for the future of federal sentencing law and post-Booker jurisprudence?  I am still scratching my head, but let me venture a few ruminations:

1.  Based on the 1996 Koon decision, I have long thought that even anti-Blakely Justices favor significant district court discretion over circuit court lawmaking in the sentence arena.  Consequently, I have always expect that the post-Booker cases would champion district court discretion (and perhaps fault excessive circuit court intervention) in sentencing determinations.

2.  The "problem" with Rita is that championing district court discretion by affirming the sentence imposed by the district court also serves, at least indirectly, to praise the guidelines.  (And, conversely, reversing in Rita might suggest reasonableness review should be aggressive.)

3.  Without the Claiborne companion, the Justices may be worried that Rita alone wont allow the development of the complete message they wish to send to lower courts about post-Booker doctrines and practices.

4.  But all the timing (and the many options) have me really puzzled.  Whatever the court does with Rita, the holding and the dicta will reverberate through the federal sentencing world ASAP.  And yet, as the Rita pebble (or boulder) ripples through the federal sentencing pond, everyone will know that the Justices have just picked up two more rocks to throw into the pond.  And, under usual timelines, we shouldn't expect rulings in Gall and Kimbrough until perhaps January 2008 or later.

5.  Sadly, I am now worried we might know who's the next President before we know what Booker really means for federal sentencing.  Oy vey.... though I guess it's good for my business.