Is it possible to successfully evade paying tax on investments?

from my understanding the IRS matches those almost 100%. I would not leave it off regardless if you think they have bigger fish to fry. You might end up paying not only the original tax owed but also extreme penalties and interest. If I were you I would invest smater if you don't want to pay taxes and find tax friendly investments. The amount of tax is probably minimal Just multiply it roughly by your marginal rate of tax.