It is very common. Children learn it from their parents in business.
We had a scandal in the past year among the Sephardic Jewish community in New York.
Most of it comes from our Eastern European heritage where many Jews only survived by cheating the government that was oppressing them.
You couldn’t be honest and survive in Czarist Russia. You’d starve to death. So Jews learned to cheat to get by.
It’s a teeny bit like Israel before Benjamin Netanyahu. It had such sky-high tax rates and oppressive bureaucracy that virtually everybody cheated on their taxes, including otherwise good people.
Reb Moshe Feinstein says very clearly that the United States is a good country, not an oppressive one like Czarist Russia, and that taxes should paid honestly. Reb Moshe wrote that because most of the people around him treated the United States government like it was Czarist Russia.
From a religious perspective, let alone an Orthodox Jewish perspective, we are at war with the society around us. The internet, the newspapers, the televisions, magazines, movies, public education, sporting events, everything is against our values. The Orthodox culture inherently dismisses the culture around it. The Modern Orthodox are selectively dismissive and the Haredim are almost totally dismissive, but both groups of Orthodox Judaism know that they are at war with the majority culture with its drug use, sexual permissiveness, gender bending, and the like.
When you feel like you are at war with the society around you, it makes you less concerned with paying taxes honestly (unless you get into the media spotlight on this issue, then the incentive is to promote the socially acceptable way).
