DEANGELO JENKINS v. UNITED STATES, 152 A.3d 585

In Jan. 2015 at Columbia Heights Village, a tenant reported an attempted armed robbery: one man brandished a gun inside a building; a second man was observed outside but did not act.
The victim gave a description of the assailant (age 21–22, 5'8"–5'9", dark complected, dreadlocks, dark ski mask and clothes) and a different description of the person outside (lighter complected, ski mask, no build/hairstyle detail).
CHV Special Police Officers (SPOs) watched surveillance footage (which did not capture the robbery) and one SPO (Mason) reportedly described a man in a black ski mask, black jacket, blue jeans, and a bicycle; Mason did not testify and the video was not produced.
Around midnight — ~10 hours after the robbery — SPOs observed appellant riding a bicycle in the complex wearing a black jacket, blue jeans, and pulling a black ski mask; SPOs stopped and frisked him and recovered guns and ammunition.
Appellant was convicted after a stipulated trial; he moved to suppress the evidence, arguing the stop lacked reasonable, articulable suspicion. The trial court denied the motion; the D.C. Court of Appeals reversed.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether SPOs had reasonable, articulable suspicion to conduct a Terry stop of appellant	Stop lacked reasonable suspicion because appellant did not match the victim’s descriptions (no dreadlocks, lighter complexion) and mere presence near the scene or association is insufficient	SPOs relied on a lookout/description from SPO Mason and surveillance review identifying a man with a ski mask, dark jacket, blue jeans, and bicycle; that matched appellant	Reversed: stop was unlawful — government failed to show specific, reliable facts supporting reasonable suspicion
Whether information passed among officers (lookout/video) provided sufficient indicia of reliability to justify the stop	Information was unreliable: the surveillance video was not produced, Mason did not testify, and Walker lacked first‑hand knowledge of the source	Government argued officers reasonably relied on the collective lookout and surveillance review	Held: unreliable — out‑of‑court descriptions/lookout could not supply reasonable suspicion absent evidence of the lookout’s basis; trial court erred

Terry v. Ohio, 392 U.S. 1 (establishing stop‑and‑frisk reasonable‑suspicion framework)
In re T.L.L., 729 A.2d 334 (D.C. 1999) (reliability requirement for information passed between officers/lookouts)
Milline v. United States, 856 A.2d 616 (D.C. 2004) (officer may rely on a police lookout only to the extent the lookout itself is based on reasonable suspicion)
United States v. Hensley, 469 U.S. 221 (police may stop based on accurate and reliable police bulletin)
Smith v. United States, 558 A.2d 312 (D.C. 1989) (rejection of guilt‑by‑association as articulable suspicion)