In the case of Reymundo Toledo-Flores v. United States (2006), the U.S Supreme Court dealt with an issue concerning immigration law and criminal sentencing. The petitioner, Reymundo Toledo-Flores, a Mexican national who had been deported from the U.S multiple times, was arrested for illegal reentry into the country. He argued that his sentence enhancement under 8 USC Section 1326(b) was unconstitutional because it exceeded maximum penalties based on facts not admitted by him or found by a jury beyond reasonable doubt - in violation of his Sixth Amendment rights as interpreted in Apprendi v New Jersey (2000). However, the court ruled against him stating that prior convictions used to enhance sentences do not need to be proven beyond reasonable doubt or admitted by defendant; they are considered sentencing factors rather than elements of crime itself. Therefore, there is no constitutional requirement for these facts to be included in indictment or proved at trial.

In the dissenting opinion for Reymundo Toledo-Flores v. United States, Justice Scalia disagreed with the majority's interpretation of a provision in an immigration law that makes it a crime to reenter the U.S. after being deported following conviction for certain crimes. He argued that Congress intended this provision to apply only when those specific crimes were part of the reason for deportation, not simply if they had been committed at any point prior to deportation. The majority interpreted "deported ... because of" as meaning "deported ... after," but Scalia contended this was inconsistent with normal usage and legislative intent, which he believed required some causal connection between deportation and criminal conviction. He also criticized their reliance on administrative practice rather than statutory text or legislative history in interpreting ambiguous laws.