We investigated how high school mathematics course placement contributes to inequalities in college preparation for students categorized as "English Learners" (ELs), especially "long-term" English Learners (LTELs). We devised a base-2 enumeration approach that allowed us to process complex transcript data from one school district and enumerate the thousands of possible trajectories (combinations) of mathematics courses taken by students during high school. We observed significant disparities in college preparation across students by English proficiency designation. In comparison to English Only (EO) students, LTELs were funneled into fewer trajectories that predominantly included lower level mathematics courses. We found that enrollment into remedial mathematics courses in Grade 9 appears to restrict access to advanced courses, with grave consequences for Grade 12 college preparation.