Lopez v. Gonzales; Toledo-Flores v. United States


If a permanent resident of the United States is convicted in state court of a drug offense that state law classifies as a felony but that federal law classifies as a misdemeanor, should the offense qualify as an “aggravated felony” for the purposes of federal immigration and sentencing law, resulting in deportation and harsher sentencing under federal law?

Oral argument: 
October 3, 2006

Both Jose Antonio Lopez and Reymundo Toledo-Flores are permanent residents of the United States who were convicted of drug crimes that are felonies at the state level but misdemeanors under federal law. The government argues that both Lopez’s and Toledo-Flores’s crimes qualify as “aggravated felonies.” If that is the case, Lopez will be barred from seeking a waiver of the deportation order issued against him while Toledo-Flores will be subject to a stricter sentence under the mandatory Federal Sentencing Guidelines. Lopez and Toledo-Flores argue that their drug crimes do not meet the definition of an aggravated felony because they are not felonies under federal law. Thus, the Court must decide whether drug offenses that are state felonies but federal misdemeanors satisfy the federal statutory definition of aggravated felony.

Questions as Framed for the Court by the Parties 

Lopez v. Gonzales

Whether an immigrant who is convicted in state court of a drug crime that is a felony under the state’s law but would only be a misdemeanor under federal law has committed an “aggravated felony” for purposes of the immigration laws.

Toledo-Flores v. United States

Has the Fifth Circuit erred in holding – in opposition to the Second, Third, Sixth, and Ninth Circuits – that a state felony conviction for simple possession of a controlled substance is a “drug trafficking crime” under 18 U.S.C. § 924(c)(2) and hence an “aggravated felony” under 8 U.S.C. § 1101(a)(43)(B), even though the same crime is a misdemeanor under federal law?


Lopez v. Gonzales, 417 F.3d 934 (8th Cir. 2005)

Jose Antonio Lopez is a permanent resident of the United States. A South Dakota state court convicted Lopez of aiding and abetting the possession of a controlled substance, a felony crime in South Dakota. Lopez v. Gonzales, 417 F.3d 934, 935 (8th Cir. 2005). Under federal law, however, Lopez’s crime is only a misdemeanor. Id. at 937. Following Lopez’s conviction, Immigration and Naturalization Services (INS) sought to deport him on two separate grounds: his commission of an “aggravated felony” and his conviction for an offense involving a controlled substance. Id. at 935.

Although Lopez conceded the controlled substance violation, as a long-time permanent resident he was eligible under the Immigration and Nationality Act (INA) to apply to the Attorney General for a cancellation of the deportation order. Lopez at 935; see also INA § 240A(a). At trial, however, the court found that Lopez could be deported both for the substance violation and for the aggravated felony. Id. at 935. Moreover, the court denied Lopez’s application for cancellation of the deportation order because INA § 240A(a)(3) prohibits the Attorney General from cancelling deportation orders against aliens convicted of aggravated felonies. Id. at 936.

Lopez objected to the classification of his drug trafficking offense as an aggravated felony because of its lesser status under federal law, and he appealed to the United States Court of Appeals for the Eighth Circuit. Lopez at 936-37. The court ruled against Lopez and affirmed his ineligibility for an appeal of deportation. Lopez at 938.

United States v. Toledo-Flores, 149 Fed.Appx. 241 (5th Cir. 2005)

In March of 2004 Reymundo Toledo-Flores, a Mexican citizen, was charged for illegally entering the United States. Brief for Petitioner Toledo-Flores at 3, Toledo-Flores v. United States (No. 05-7664). Prior to this charge, in 2002, Toledo-Flores was convicted in Texas state court of possession of cocaine. Id. In Texas, this crime of possession is classified as a felony offense, whereas federal law classifies simple possession of cocaine as a misdemeanor. Id.

When sentencing Toledo-Flores’s for illegally re-entering the United States, the district court classified his prior conviction for possession of cocaine as an aggravated felony for the purposes of the Federal Sentencing Guidelines. United States v. Toledo-Flores, 149 Fed.Appx. 241, 242 (5th Cir. 2005). As a result, the court increased Toledo-Flores’s mandatory sentence from a range of eighteen to twenty-four months to a range of thirty-three to forty-one months. See Brief for Petitioner Toledo-Flores at 4. Toledo-Flores appealed to the Court of Appeals for the Fifth Circuit, arguing that, because federal law classifies his crime as a misdemeanor, the lower court incorrectly classified it as an aggravated felony. Brief for Petitioner Toledo-Flores at 4. The Fifth Circuit affirmed the lower court. Toledo-Flores at 242.

The Supreme Court has consolidated Lopez and Toledo-Flores’s cases and will hear their oral arguments together.


Lopez’s and Toledo-Flores’s Argument

Toledo-Flores first contends that the lower court’s decision conflicts with Jerome v. United States, in which the Supreme Court decided that the forgery of a promissory note, a felony under Vermont law but not under federal law, did not qualify as a violation of the Bank Robbery Act. Toledo-Flores, at 242 (citing 318 U.S. 101 (1943)). Under Jerome, a court is required to assume that federal acts are not dependent upon state law, unless Congress makes a clear statement to the contrary when enacting a statute. Id. Toledo-Flores suggests that Jerome controls here, and that the only permissible way for the statute to be read is by applying the federal felony approach. Brief for Petitioner Toledo-Flores, at 43.

Lopez first argues that the failure to distinguish between mere drug possession crimes and “illicit trafficking” is erroneous because it ignores the clear difference between the two behaviors. Brief for Petitioner Lopez, at 13. As the American Civil Liberties Union points out, the term trafficking “necessarily involves commercial activity,” not mere possession. Brief for Amici Curiae, American Civil Liberties Union et al., at 12, Lopez v. Gonzalez (No. 05–547), Toledo-Flores v. United States (No. 05–7664). The American Bar Association also urges the court to read the provision narrowly, agreeing that the “[i]llicit trafficking aggravated felony provision [must be] limited to felonies that involve trafficking.” Brief of the American Bar Association as Amicus Curiae, at 6, Lopez v. Gonzalez (No. 05–547), Toledo-Flores v. United States (No. 05–7664).

Both Lopez and Toledo-Flores then focus on the definition of “drug trafficking crime,” which includes the qualifying phrase “a crime for which the person may be prosecuted in a court of the United States.” 18 U.S.C. § 924(c)(1). Lopez and Toledo-Flores argue that this language limits the application of the definition to federal offenses, particularly given the fact that other provisions of § 924 mention state offenses specifically when they are meant to be included. Brief for Petitioner Lopez, at 14. Lopez and Toledo-Flores also explore the language used by Congress while they made changes to Title 18 in 1988, and suggest that Congress intended to clarify that “possession with intent to distribute a controlled substance” is a drug trafficking crime; Congress did not, however, intend to expand drug trafficking crime to include state offenses “that are neither drug trafficking crimes nor federal felonies.” Id., at 15.

Finally, both Lopez and Toledo-Flores point to Public Law no. 99-603, § 115, 100 Stat. 3359, 3385 (1986), which establishes that all federal law dealing with immigration must be interpreted to apply equally to all non-citizens throughout the country. Id., at 16. They argue that the revisions to the INA create an ambiguous legislative history that makes it difficult to discern a single legislative intent. Id., at 37. Under common rules of statutory construction, where immigration law includes ambiguous language, that ambiguity should be resolved in favor of non-citizens. Brief for Petitioner Toledo-Flores, at 37–38.

In an effort to reduce the variations in law that have arisen under the current approach, Lopez and Toledo-Flores advocate for the federal felony approach that would limit the term “aggravated felony” to crimes that are felonies under law. Brief for Petitioner Toledo-Flores, at 40–41.They contend that this interpretation of the law will lead to more uniform treatment of non-citizens throughout the country, and that the state felony approach may in fact raise constitutional issues due to the disparate outcomes that it creates for non-citizen offenders in different states. Id. at 42. They argue that under the current system, non-citizens in one state may be found to have committed “drug trafficking crime” for the same conduct punished far less stringently in a neighboring state. Id. at 40-41.

The Government’s Argument

As a threshold matter, the government argues that Toledo-Flores’s case is moot, because Toledo-Flores has based his challenge on the aggravated-felony enhancement of his prison sentence, the full term of which he has already served. Brief for Respondents, at 8. The government argues that since a ruling in Toledo-Flores’s favor will not make a difference in his sentence, he has no standing to bring his claim before the court. Id.

Second, the government contends that any drug crime that is a felony under federal or state law and also punishable under the Controlled Substances Act should be considered an aggravated felony for the purposes of the INA and the FSG. Id., at 8. They point out that the definition of a “drug trafficking crime” in § 924(c)(2) specifically includes eligible offenses under the Controlled Substances Act “whether in violation of Federal or State law.” Id., at 13. The government focuses on the plain meaning of the language in each of the relevant statutes, and interpret the phrase “punishable under the Controlled Substances Act” in § 924(c)(2) to mean any conduct that is “liable to” or “capable of being punished by” the law, rather than conduct that has already led to a conviction under federal law. Id., at 17–18. They address the qualitative difference between “trafficking” and “possession” by arguing that the presumption established in Jerome is overcome by the specificity of Congress’s language in the INA. Id., at 22–24. They point out other parts of the statute where Congress distinguished between state and federal offenses as well, and suggest that where Congress has in one Act used precise language in some sections and general language in others, it is standard to interpret this as a deliberate congressional decision. Id., at 18.

Furthermore, the government points out that the definition of a “felony,” established under Title 18, focuses on the gravity of a particular crime, as measured by the length of the sentence imposed: “a felony is any crime for which the sentence is one year or more.” Id., at 9. As a result, if an individual is convicted of a drug crime and sentenced to any amount of time greater than one year, his crime falls within the range of crimes that Congress meant to reach, regardless of whether the crime would be classified a “felony” under federal or state law. Id.

Third, the government argues that including state-law felonies in the definition of “felony” will comport with congressional intent. Id., at 42–43. They point to statements made by members of Congress regarding the 1990 INA amendment, in concert with the language of the changes, to suggest that they were attempting to “cover all drug felonies”—both state-law and federal-law offenses—in an effort to “eradicate the demand for illicit drugs, not just the supply.” Id.

Finally, the government claims that that the federal felony approach favored by Lopez and Toledo-Flores introduces arbitrariness and inequity of its own. Id., at 9. For example, in a state with drug laws similar to the federal laws, possession of anything more than a personal-use quantity of marijuana would constitute an aggravated felony. Id. If the neighboring state did not follow the same scheme, a similarly-situated individual could be arrested with a substantially larger quantity of marijuana and, although he would likely be subject to a longer sentence, he still might not have committed an aggravated felony. Id. The government further argues that any constitutional concerns raised by Lopez and Toledo-Flores are unfounded, since the lack of uniformity in the state felony approach derives from variations in state law that are a natural and necessary part of the federal system. Id. at 47–48.


Under current immigration law, any lawful permanent resident convicted of a drug-related crime may be deported. 8 U.S.C. § 1227(a)(2)(B)(i). For people who have built lives and families in the United States, a forced “return” to a place they may not recognize can be disorienting or even dangerous. Sophia Hanifah, “A New Nightmare: Cambodian American Deportation Carries History’s Weight,” AsiaWeek, November 22, 2002. In recognition of this, the law allows people to appeal the deportation order. 8 U.S.C. § 1229b. However, if an individual is convicted of a drug offense that is an “aggravated felony,” the individual becomes ineligible for cancellation of removal. See INA § 240A(a)(3).

Both Lopez and Toledo-Flores were convicted of possession of a controlled substance, and in both cases, their convictions render harsher consequences if their crimes are construed as aggravated felonies. In Lopez’s case, an aggravated felony conviction renders him ineligible for the Attorney General’s waiver of the removal order. INA § 240A(a)(3). In Toledo-Flores’s case, an aggravated felony increases the minimum sentencing range to which he is susceptible under the Federal Sentencing Guidelines. USSG § 2LI.2(c). For the purposes of both the INA and the Federal Sentencing Guidelines, the definition of aggravated felony depends upon the definition of “drug trafficking crime” provided in 18 U.S.C. § 924(c)(2). See INA § 101(a)(43)B); see also 8 U.S.C. § 1101. According to § 924(c)(2), a drug trafficking crime is “any felony punishable under the Controlled Substances Act” (CSA). 18 U.S.C. § 924(c)(2). The Fifth and Eighth Circuits found that because Lopez’s and Toledo-Flores’s crimes were felonies under state law, they amount to felonies punishable under the CSA. Lopez, at 937; Toledo-Flores, at 242. As a result, their crimes were “drug trafficking crimes” and, therefore, aggravated felonies for the purposes of the INA and the Federal Sentencing Guidelines, even though they were misdemeanors under federal law. Id. Lopez and Toledo-Flores characterize this as the “state felony approach.” See Brief for Petitioner Toledo-Flores, at 6. The Second, Third, Sixth, Seventh and Ninth Circuits, by contrast, have followed the “federal felony approach” in holding that any crime that is not a felony under federal law (such as the offenses for which Lopez and Toledo-Flores were convicted) cannot be considered an aggravated felony for statutory purposes. See Id., at 12.

Lopez and Toledo-Flores both advocate for the federal felony approach. They maintain that their drug crimes did not constitute “drug trafficking” for two reasons. First, they appeal to the literal meaning of the word trafficking and point out that they did not sell or distribute controlled substances. Brief for Petitioner Lopez, at 13, Lopez v. Gonzalez (No. 05–547). Alternatively, they argue that when interpreting § 924(c)(2), only drug crimes that are federal felonies should be considered felonies “punishable under the Controlled Substances Act.” Brief for Petitioner Lopez, at 21-25.

The government argues the relevant language from that § 924(c)—“any felony punishable under the Controlled Substances Act”—should be read to mean that any drug crime that is prohibited by the CSA and that is characterized as a felony, whether at the state or federal level, is a felony under the Controlled Substances Act. Brief for Respondents, at 8, Lopez v. Gonzalez (No. 05–547), Toledo-Flores v. United States (No. 05–7664). The government also argues that Congress has traditionally given the term “felony” an expansive meaning; it does not refer to federal felonies exclusively, but to conduct that the convicting jurisdiction punishes with one year or more of prison. Id., at 9. Where that is the will of the legislature, it should be applied throughout the country, an approach that will promote uniform sentences across jurisdictions. Id., at 9–10.

Under either scheme, the Court’s decision in this case will bring uniformity to the circuits by clarifying the role of state law in establishing the definition of “any felony punishable under the Controlled Substances Act.” This, in turn, will clarify the scope of the definition of “drug trafficking,” and “aggravated felony” for the purposes of the INA and the Federal Sentencing Guidelines. In an amicus brief, a group of drug court administrators raise an additional, less intuitive consequence. Under the state felony approach, the drug courts’ ability to coerce non-citizens to participate in rehabilitation programs will be severely hampered, since non-citizens with felony convictions on their records could face mandatory deportation regardless of whether they successfully complete a treatment program. Brief of Amici Curiae Center for Court Innovation and the New York Association of Drug Treatment Court Professionals, at 15–20, Lopez v. Gonzalez (No. 05–547), Toledo-Flores v. United States (No. 05–7664).


This case signifies an important decision in sentencing and immigration policy which has the potential to affect the lives of many non-citizens who reside in the United States. If Lopez and Toledo-Flores prevail, drug crimes that are felonies at the state level but misdemeanors under federal law will not be considered aggravated felonies for the purposes of federal law. If the government prevails, any non-citizen who commits a drug offense that is a felony at the state level will be sent back to their country of origin without further consideration. In addition, the decision will affect sentencing and indicate whether this country is moving towards harsher punishment for drug offenses. However this case is resolved, the court’s decision will significantly impact drug law and sentencing, and will also have implications for immigration law that cannot be ignored.Written by:

Molly Curren Rowles

Jill Diamond


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