Federal sentencing error as loss of chance.

In July 2010, a federal district court sentenced DeAngelo Whiteside to seventeen years and six months in prison for a drug offense. (1) Under Fourth Circuit precedent, Mr. Whiteside's two prior state drug convictions triggered application of the Federal Sentencing Guidelines' "career offender" enhancement. (2) On the facts of Mr. Whiteside's case, the Guidelines recommended between twenty-one and twenty-eight years in prison. (3) The district court arrived at its ultimate sentence after granting the government's motion for a shorter sentence due to Mr. Whiteside's cooperation. (4)

If Mr. Whiteside had been sentenced just over a year later, he would not have been a "career offender." (5) In 2011, the Fourth Circuit determined that the Circuit had misinterpreted which state convictions qualify as "prior felony convictions" that trigger the career offender enhancement. (6) Under the proper interpretation, Mr. Whiteside's prior offenses would not have warranted a heightened recommended sentence. (7) Instead, the Guidelines would have recommended a maximum prison term of roughly fourteen years and six months. (8) Assuming the same downward departure, Mr. Whiteside's sentence, if determined today, would be nine years and four months--a difference of about eight years of his life. (9)

Federal courts are currently locked in a debate over what to do with sentences like Mr. Whiteside's, in which the sentencing court misapplied (10) the Federal Sentencing Guidelines' career offender enhancement. (11) The core issue in this debate is whether misapplication of the Guidelines may be challenged post-conviction on collateral review. (12) In these cases, the sentencing court's application of the legal standard for career offender status has been invalidated, typically because the circuit's interpretation of a "prior felony conviction" has changed. (13) The sentencing court's use of that legal standard is, in retrospect, an erroneous application of law. (14) The question is whether such misapplications of law are cognizable in a later challenge under 28 U.S.C. [section] 2255. (15)

The test for cognizability in these cases is whether sentencing error constitutes a "complete miscarriage of justice." (16) If it does, then sentences like Mr. Whiteside's can be challenged on collateral review; if it does not, these sentences stand. Of the four circuits that have applied this test, the Seventh, Eighth, and Eleventh have held that career offender misapplication is not a fundamental miscarriage of justice. (17) The First Circuit recently found a career offender claim cognizable on its facts but declined to consider whether sentencing errors arising from a change in legal interpretation give rise to a [section] 2255 challenge. (18) In Whiteside, after a Fourth Circuit panel held that the error amounted to a fundamental miscarriage of justice, an en banc court reversed on the grounds that Mr. Whiteside's appeal was untimely. (19) All of these decisions, except the First Circuit's, hinged on a single vote. (20) Two were en banc. (21)

This Comment argues that courts have taken the wrong approach to cognizability. Circuit court opinions, and scholarly analysis of these opinions, have framed the argument over misapplication of the career offender enhancement as a conflict between individual fairness--the righting of a wrong by the legal system to an erroneously sentenced individual--and finality-the criminal justice system's interest in leaving final sentences undisturbed. (22) This Comment contends that disagreement over the cognizability of these claims is actually about the nature of the harm in sentencing error. What federal courts are asking, in effect, is whether the lost probability of a lower sentence is itself a cognizable injury. Despite the prevalence of language about "probability" and "risk" in the career offender opinions, (23) courts rarely articulate the sentencing debate in these terms. This Comment focuses on the latent probability analysis in sentencing opinions. It argues that a new approach to cognizability--one characterized in terms of probability-would better address the harm at stake in sentencing.

The Comment proceeds in two Parts. Part I draws on an analogy to tort law to argue that sentencing debates are, at their core, about loss of chance. This Part highlights the role that probability plays in recent sentencing opinions. It argues that, as an empirical matter, loss of chance is an accurate way to describe sentencing error given the "anchoring effect" of the Guidelines on sentencing practices.

Part II makes the structural case for conceptualizing Guidelines sentencing error as a problem of probability. This Part argues that failure to recognize the probability dispute has obscured important debates about the continued vitality of the Guidelines system. After United States v. Booker, the Sentencing Guidelines are advisory in principle and influential in practice. (24) Part II argues that treating Guidelines error as loss of chance--a loss that can constitute a fundamental miscarriage of justice in the career offender context--is necessary in order to enforce a Guidelines regime that is neither too rigid nor wholly indeterminate. The Comment concludes that a loss of chance framework can help address core concerns in federal sentencing law.

1. THE PROBABILITY DEBATE

   In appellate court opinions on career offender misapplication, judges have framed the debate over sentencing error in terms of fairness and finality. (25) Circuit courts that have held career offender misapplication not cognizable have emphasized the need for finality in order to minimize systemic burdens on the justice system. (26) In contrast, courts that have held sentencing error cognizable have stressed fairness to individual defendants. (27) The Fourth Circuit, for example, characterized its holding that career offender error is a fundamental miscarriage of justice as a determination that finality should not "outweigh the plain injustice" of precluding post-conviction review. (28) In holding career offender error non-cognizable, the Seventh Circuit majority faulted the dissent for failing to recognize "the difficulty of balancing 'fairness' (meaning what exactly?) against finality." (29) The Eleventh and Eighth Circuit opinions (30) and academic discussion (31) feature similar language.

   This line of discourse has obscured the significance of the advisory Guidelines sentencing regime to these cases. In 2005, United States v. Booker invalidated the provisions of the Federal Sentencing Act making the Sentencing Guidelines mandatory. (32) Now, though federal courts still determine the recommended Guidelines sentence, that determination is not binding. The shift to an advisory regime leaves the Guidelines' juridical status unclear. The Supreme

   Court has called the advisory Guidelines the "lodestone" (33) and "the starting point and initial benchmark" (34) of federal courts' sentencing. (35) Yet Booker describes the Guidelines as "merely advisory," and the significance of an "advisory" system is hotly contested. (36) Ultimately, disagreement over career offender resentencing is about the meaning of the post-Booker Guidelines: is the probability of a higher sentence due to Guidelines error a harm of its own?

   Circuit court opinions on sentencing error do not treat the probabilistic question inherent in these cases in a systematic way; they do not even use the phrase "loss of chance." (37) But the valuative and the empirical questions running through the career offender debate are the essential questions of probabilistic analysis: whether Guidelines error represents a lost opportunity for a better outcome and the value of that loss to the person harmed. Courts disagree about whether missing out on the chance of a lower sentence can ever be a fundamental miscarriage of justice.

   1. Chance as Value

      When cast in these terms, the sentencing misapplication argument raises issues analogous to those implicated by the loss of chance approach in tort law. In medical malpractice cases, many jurisdictions use the loss of chance approach. (38) The idea underlying this doctrine is that the opportunity for a better outcome itself has value, such that deprivation of that chance may be a legally actionable harm. (39) Sentencing error debates can be understood along similar lines. Judges who argue that career offender misapplication may be a fundamental miscarriage of justice see the chance of a lower sentence as a harm in itself. (40) Those who reject cognizability do not view the probability of a different sentence as a harm requiring review because, even with a different Guideline recommendation, the judge may re-sentence the offender to the same term. (41)

      In the medical malpractice context, loss of chance typically involves a two-step, proportional recovery analysis. (42) In the first step, the injury is conceptualized as the loss of an opportunity for a better outcome. (43) This characterization enables the plaintiff to recover when she cannot demonstrate preponderance-of-the-evidence causation of the ultimate injury but can show that it is more likely than not that the harm caused a diminished likelihood of a positive outcome. (44) Imagine, for example, that a person who died of cancer initially had a forty-percent chance of recovery, but that her physician's negligence decreased her chances to twenty-five percent. This person's estate could not prove that the physician's negligence caused her death. (45) But a loss of chance framework would cast the fifteen-percentage-point diminution in the possibility of recovery as a legally cognizable harm. (46) The loss of chance doctrine thus allows plaintiffs to recover where they otherwise might not.

      Judges and scholars also use probabilistic reasoning in non-medical contexts. The Seventh Circuit applies a loss of chance approach to damages in employment discrimination cases. (47) When a fire department...