United States v. Dennis M. Shepheard, 706 F. App'x 526

Background

Dennis Shepheard was convicted after a bench trial before a magistrate of two counts of making harassing communications under Ala. Code § 13A-11-8(b), assimilated via the Assimilative Crimes Act.
He made hundreds of telephone calls to VA employees over six weeks, often repeated within minutes, intending to harass and to learn who authorized a transfer of his banking information.
The district court affirmed the magistrate judge’s conviction and 24-month probation, which included a special condition barring telephone contact with VA facilities except for medical/appointment purposes.
On appeal to this Court, Shepheard argued (1) his calls fell within the statute’s “legitimate business telephone communications” safe harbor, or alternatively that the statute is unconstitutionally vague as applied; and (2) the special probation condition was an abuse of discretion.
The Eleventh Circuit affirmed: the safe-harbor does not cover unreasonable, harassing calls made in the guise of business purposes; the statute is not vague as applied to these facts; and the probation condition was substantively reasonable and related to the offense.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether repeated calls are protected as "legitimate business telephone communications" under Ala. Code § 13A-11-8(b)	Shepheard: safe harbor covers harassment if in furtherance of a legitimate business purpose; "legitimate" is an objective reasonableness standard that could include business harassment	State: safe harbor protects only reasonable, legitimate business calls; harassment is not reasonable even if for business ends	Court: Safe harbor does not cover objectively unreasonable, harassing calls; Shepheard's repeated calls were not legitimate and thus not protected
Whether the statute is unconstitutionally vague as applied	Shepheard: statute fails to give fair notice when calls become unreasonable and could permit arbitrary enforcement	State: statute provides sufficient clarity as applied to extreme repeated-calling conduct	Court: As-applied vagueness challenge fails — ordinary person would know hundreds of calls over six weeks (some every few seconds) are unreasonable
Whether the probation special condition barring phone contact with VA facilities was substantively unreasonable	Shepheard: condition overly restrictive, hinders lawful contact with VA	State: condition reasonably related to offense, tailored with exceptions for medical needs and other contact means	Court: Condition is substantively reasonable, related to offense, prevents means of harassment and contains reasonable exceptions
Standard of review for these issues	—	—	Vagueness reviewed de novo; probation-condition review for abuse of discretion/substantive reasonableness per Cothran and § 3563(b)

Key Cases Cited

Junkins v. Glencoe Volunteer Fire Dep’t, 685 So. 2d 769 (Ala. Civ. App. 1996) (statutes given practical construction to avoid absurd results)
P.J.B. v. State, 999 So. 2d 581 (Ala. Crim. App. 2008) (statutes must be reasonably interpreted and not lead to absurd results)
First Union Nat. Bank of Fla. v. Lee Cty. Comm’n, 75 So. 3d 105 (Ala. 2011) (courts must give effect to legislature's intent by examining statute as a whole)
Donley v. City of Mount Brook, 429 So. 2d 603 (Ala. Crim. App. 1982) (safe harbor covers reasonable single consumer or business contacts)
Ex parte Donley, 429 So. 2d 618 (Ala. 1983) (related discussion of scope of communications protections)
United States v. Cothran, 855 F.2d 749 (11th Cir. 1988) (standard for reviewing probation conditions for abuse of discretion)
United States v. Taylor, 338 F.3d 1280 (11th Cir. 2003) (upholding special condition barring internet access after harassment via internet)
United States v. Irey, 612 F.3d 1160 (11th Cir. 2010) (standards on substantive reasonableness of sentences)
Holder v. Humanitarian Law Project, 561 U.S. 1 (2010) (as-applied vagueness analysis; clarity as applied defeats vagueness challenge)
United States v. Nelson, 712 F.3d 498 (11th Cir. 2013) (void-for-vagueness framework for criminal statutes)
United States v. Pilati, 627 F.3d 1360 (11th Cir. 2010) (standard of review where magistrate trial reviewed by district court)