First impressions are rarely accurate. At least mine, anyway. So when I first read Justice Sotomayor’s concurring opinion in Freeman v. United States, No. 09-10245, I didn’t think much of it. The number of guideline amendments that turn retroactive is few as are Rule 11(c) plea agreements. But giving the opinion a closer look, combined with the Sentencing Commission’s passage of retroactivity for a guideline amendment involving crack cocaine offenders, I think her opinion could have a broader impact than I originally thought.

Let me explain.

A few weeks ago, the U.S. Sentencing Commission made amendment 750 retroactive. The amendment’s effect is to lower the guideline range for crack cocaine offenders. Prisoners who meet the criteria of 18 U.S.C. § 3582 can start applying for a sentence reduction after November 1, 2011.

Section 3582(c)(2) states that:

in the case of a defendant who has been sentenced to a term of imprisonment based on a sentencing range that has subsequently been lowered by the Sentencing Commission pursuant to 28 U.S.C. 994 (o), upon motion of the defendant or the Director of the Bureau of Prisons, or on its own motion, the court may reduce the term of imprisonment, after considering the factors set forth in section 3553 (a) to the extent that they are applicable, if such a reduction is consistent with applicable policy statements issued by the Sentencing Commission.

Some prisoner advocacy groups—and the federal government—believe that the new amendment does not apply to crack cocaine offenders sentenced as career offenders because their guideline ranges were not “based on” crack cocaine. Rather, they say, the guideline ranges were based on the individual’s prior convictions and the statutory maximum for the offense of which they were convicted.

A circuit split in fact exists on whether career offenders are eligible to benefit from amendment 712­–a similar amendment to 750–which the Commission made retroactively applicable in 2007. See and compare, United States v. Cardosa, 606 F.3d 16 (1st Cir. 2010) (defendant eligible for § 3582 reduction), United States v. McGee, 553 F.3d 225, 228 (2d Cir. 2009) (same); United States v. Munn, 595 F.3d 183, 192-93 (4th Cir. 2010) (same); with, United States v. Guyton, 636 F.3d 316, 320 (7th Cir. 2011) (holding that defendant ineligible for sentence reduction); United States v. Payton, 617 F.3d 911, 913-14 (6th Cir. 2010) (same); United States v. Darton, 595 F.3d 1191, 1197 (10th Cir.) (same), cert. denied, 130 S. Ct. 3444 (2010); and United States v. Tolliver, 570 F.3d 1062, 1066 (8th Cir. 2009) (same).

The circuit split was recently resolved in favor of not applying retroactive amendments to career offenders. See Amendment 750 (“Consistent with the three-step approach adopted by Amendment 741 and reflected in §1B1.1, the amendment adopts the approach of the Sixth, Eighth, and Tenth Circuits and amends Application Note 1 to clarify that the applicable guideline range referred to in §1B1.10 is the guideline range determined pursuant to §1B1.1(a), which is determined before consideration of any departure provision in the Guidelines Manual or any variance.”).

A large part of the circuit dispute turns on what is meant by § 3582(c)(2)’s statement limiting resentencing to a “term of imprisonment based on a sentencing range that has subsequently been lowered by the Sentencing Commission.”  

And that “based on” language was also the crux of the dispute between the plurality, concurring and dissenting opinions in Freeman. See Freeman (C.J. Roberts dissenting) (“The lone issue here is whether petitioner William Freeman meets the initial prerequisite of having been sentenced to a term of imprisonment “based on” a subsequently reduced sentencing range.”).

Justice Sotomayor’s concurring opinion in Freeman (which arguably controls under a Marks’ analysis) construed the “based on” language coterminous with “use” or “employ.”  This is more expansive than the courts above who think that it is the initial base offense level that determines what a sentence is “based on.”

Under Justice Sotomayor’s reading, an individual initially determined to be a career offender, but who received a departure from the career offender guideline and was given a sentence employing a crack cocaine guideline, can benefit from amendment 750.

That position conflicts with the Sentencing Commission’s recent pronouncement and it will be interesting to see how this plays out in the courts of appeals.

Whatever happens, prisoners with career offender designations who received departures should surely file for resentencing. There is nothing to lose but some paper and postage stamps!