Did the education system fail David Levinsky?
The educations system truly did fail David Levinsky both in Russia and in America. Let's look at both in order to answer your question fully.
In Russia, Levinsky loses the draw of education when his mother is killed by a mob. This happens when this one particular young Jewish man is mugged by a group of (supposed) Christians on Easter Day. Levinsky's mother approaches the mob in order to help protect her son and is consequently killed. This horrible experience causes Levinsky to shy away from his Russian Jewish heritage idea of gaining education and continuing on the same path; therefore, he becomes enticed by Matilda and travels to America with only pennies in his pocket.
Opposed to formal education, it is Levinsky's innate knowledge of business (very much a stereotype of the Jewish mentality) that secures his success, but does not provide him happiness. This can be shown in his attempts to save a bit of money for college in New York, but at any whim of adventure, Levinsky spends all of the money and, as eNotes so expertly relates, he "abandons all thought of continuing formal education."
I found myself in the vicinity of the City College. As I passed that corner I studiously looked away. I felt like a convert Jew passing a synagogue.
Formal education, Levinsky finds, is not needed to achieve financial success; however, the lifestyle he has chosen unfortunately does not provide him happiness.