I discuss a variety of challenges to upward departures here. If you've read them, you know that the validity of the aggravating factor of "on supervision" is currently under review with the Oregon Supreme Court in a case called St v. Speedis. [Update: On June 30, 2011, the Supreme Court upheld the use of the nonenumerated enhancement factors, rejecting defense arguments that non enumerated enhancement factors violated due process and separation of powers. See State v. Speedis, 350 Or 424 (2011).] It seems that's the most commonly alleged enhancement factor. Even if the non-enumerated argument loses at the Oregon Supreme Court, the back-up argument is that the aggravating factor must be "so exceptional that imposition of the presumptive sentence would not accomplish the purposes of the guidelines." For repeat offenders, being on some form of supervision at the time of the new offense is far from exceptional. If something is commonplace, it's not exceptional.
The next most common allegation is "persistent involvement." This post is part one of a discussion of persistent involvement, and why it isn't as easy to prove as the state usually assumes.
Oregon Administrative Rule 213-008-0002(1)(b)(D) states:
"(D) Persistent involvement in similar offenses or repetitive assaults. This factor may be cited when consecutive sentences are imposed only if the persistent involvement in similar offenses or repetitive assaults is unrelated to the current offense." [Emphasis added.]
In other words, crimes that are at all "related" to the crime being sentenced - and "related" is much broader than just about any other standard other than relevancy - cannot be used as a basis for finding "persistent involvement."