One way of getting a longer prison sentence than is warranted by a present offence is to have a bad record of previous criminality.
Sometimes statutory sentencing regimes spell this out. One approach is to exhaustively list the prior offences that will serve to increase a subsequent sentence, and to require courts to apply that list regardless of the particular facts that gave rise to earlier convictions. Another statutory approach is to state the quality of previous offending that will increase a subsequent sentence.
This latter approach came under scrutiny in Chambers v United States  USSC 13 January 2009.
Here, the present offending received an increased sentence if the previous offending included a specified number of offences that were defined as violent felonies because they, inter alia (to mention only the critical point in this case) were
"... burglary, arson, or extortion, involve[d] the use of explosives, or otherwise involve[d] conduct that present[ed] a serious potential risk of physical injury to another"
(Armed Career Criminal Act 18 U.S.C. section 924(e)(2)(B)(ii); this is referred to as the residual clause).
The question was whether a previous conviction for failing to report for weekend imprisonment counted as a "violent felony". The lower courts had held that failure to report was a form of escape from a penal institution, and was therefore a violent felony because of the risk of harm posed by the aggressive behaviour of escape. The Supreme Court disagreed.
This required Breyer J (delivering the opinion of the Court in which Roberts CJ, Stevens, Scalia, Kennedy, Souter and Ginsburg JJ joined), to distinguish the established approach of characterising previous offending by type of offence without reference to particular facts, from the process of determining whether a previous instance of offending fell within a specified type of offence. This latter required reference not just to the way offences were grouped in the statute that created them, but to the characteristics of the particular definitions within such a group. Here, failure to report was grouped in the relevant statute with escaping from custody. But failure to report was a form of inaction, not having the aggressive quality of escaping:
"The behavior that likely underlies a failure to report would seem less likely to involve a risk of physical harm than the less passive, more aggressive behavior underlying an escape from custody."
Furthermore, there was no significant evidence that a non-reported would pose a risk of violence:
"The offender's aversion to penal custody, even if special, is beside the point. The question is whether such an offender is significantly more likely than others to attack, or physically to resist, an apprehender, thereby producing a "serious potential risk of physical injury.""
Therefore the previous conviction did not count towards qualification for an increased sentence in this case.
Justice Alito, with Thomas J concurring, agreed in the result but called on Congress to create a specific list of defined crimes that are deemed worthy of attracting the sentencing enhancement.
"ACCA's residual clause is nearly impossible to apply consistently. Indeed, the "categorical approach" to predicate offenses has created numerous splits among the lower federal courts, ... the resolution of which could occupy this Court for years. What is worse is that each new application of the residual clause seems to lead us further and further away from the statutory text. Today's decision, for example, turns on little more than a statistical analysis of a research report prepared by the United States Sentencing Commission." [footnote omitted]
Plainly there is a need to avoid the sentencing courts having to make detailed inquiries into the significance of instances of prior offending, while at the same time providing a categorical approach that will deal appropriately with individual offences. In Chambers the present offence (being a felon in possession of a firearm) would have attracted a minimum sentence of 15 years' imprisonment if the prior offending qualified. That would – had the views of the lower courts prevailed – have given enormous significance to the offender's failure to report for weekend detention (he had failed to report for four weekends out of an eleven weekend sentence which had been imposed for a robbery and battery offence which itself qualified to be included in the present calculation). The Court does not say what sentence Mr Chambers received for the failure to report.
There are easier ways of sentencing recidivists. One is to leave it to the judges, but as politicians can gain votes by promoting harshness it is inevitable that legislators will intervene. Some jurists favour this. Such intervention could be by reference to previous sentences of imprisonment as criteria for increasing subsequent sentences. That approach avoids the difficulty of classifying offences.