United States v. Antonio Figueroa, 2012 U.S. App. LEXIS 11747

Section 3B1.1 provides a two- to four-level enhancement for organizers, leaders, managers, or supervisors in a criminal enterprise, with Application Note 4 guiding leadership analysis.
The district court applied a two-level enhancement under 3B1.1(c) to the defendant, treating him as a middle manager in a four-participant drug conspiracy.
The defendant supervised Cruz, who obtained heroin in Texas and transported it to Chicago for distribution; Cruz and the defendant, plus Primo and Individual A, formed the core participants.
Evidence suggested the enterprise was ‘otherwise extensive’ due to geographic scope and large drug quantities (Cruz transported up to 37 kilograms of heroin; wholesale value up to $2.5 million).
The defendant argued he was merely a conduit or cutout with little discretion, but the court found his supervision continuous and as a middle manager, he occupied a supervisory status.
The court affirmed, concluding the defendant was Cruz’s supervisor and thus entitled to the manager/supervisor sentencing framework.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether 3B1.1 applies to middle managers	Defendant argues 3B1.1 applies only to organizers/leaders, not middle managers.	Prosecution contends the same framework and factors apply to managers/supervisors if warranted by extent.	Yes; the court treats middle managers under 3B1.1 as within the same framework.
Whether the enterprise was ‘otherwise extensive’	Prosecution asserts geographic scope and large drug quantities satisfy extensiveness.	Defendant asserts fewer participants undermine ‘otherwise extensive’.	Enterprise was ‘otherwise extensive’ given geography and quantity.
Whether the defendant’s role as supervisor was continuous	Prosecution contends he continuously supervised Cruz and controlled drug operations.	Defendant argues minimal discretion, akin to a conduit.	Supervisor role was continuous and functional.

United States v. Pabey, 664 F.3d 1084 (7th Cir. 2011) (defines ‘otherwise extensive’ considerations)
United States v. Diekemper, 604 F.3d 345 (7th Cir. 2010) (discusses hierarchy and roles under 3B1.1)
United States v. Thiongo, 344 F.3d 55 (1st Cir. 2003) (nature of organizational extent)
United States v. Vasquez-Rubio, 296 F.3d 726 (8th Cir. 2002) (extensiveness and participants/outsiders)
United States v. Yarnell, 129 F.3d 1127 (10th Cir. 1997) (circuits’ treatment of leadership factors)
United States v. Booth, 309 F.3d 566 (9th Cir. 2002) (application of leadership factors to supervisors)
United States v. Brown, 944 F.2d 1377 (7th Cir. 1991) (extensiveness considerations in small enterprises)
United States v. Herrera, 878 F.2d 997 (7th Cir. 1989) (historical views on extent and roles)
United States v. Childress, 58 F.3d 693 (D.C. Cir. 1995) (extensiveness and participation doctrine)
United States v. Meyers, 847 F.2d 1408 (9th Cir. 1988) (role distinctions in organizing offenses)
United States v. Cali, 87 F.3d 571 (1st Cir. 1996) (limitations of seven-factor test for managers)