US v. Simmons: Simmons pleaded guilty to three drug charges after the Government filed an information under 21 USC 851 to enhance his sentence based on a prior conviction. The prior at issue is a 1996 North Carolina conviction for possession with intent. Under North Carolina law, which ties statutory sentencing maximums to criminal history, Simmons could not have been sentenced to a term of more than 12 months in prison for that offense, as needed to trigger the 851 provisions. However, someone with the worst possible criminal history could have received such a sentence. Under Fourth Circuit law at the time of his sentencing, the conviction therefore triggered the provisions of 851.
After Simmons's sentence was affirmed on appeal, the Supreme Court GVR'd in light of Carachuri-Rosendo v. Holder. On remand, the Fourth Circuit held that Carachuri-Rosendo did not undermine the earlier circuit precedent and again affirmed the sentence. Specifically, the court rejected Simmons's argument that Carachuri-Rosendo required the court to abandon its "hypothetic defendant" analysis when examining prior convictions. The court held that the difference in statutory language between the immigration laws at issue in Carachuri-Rosendo and 851 showed the rule of Carachuri-Rosendo could not be imported into the 851 context. Carachuri-Rosendo was simply "inapplicable to our present inquiry." The court also rejected Simmons's argument with regards to whether his prior conviction was obtained in violation of his right to counsel.
UPDATE: See here, reversed en banc.