There are two basic references where one can START learning about this stuff.
The first is the instruction booklet the IRS publishes each year for the 1040 tax return (long form). That's the return you'll be signing. On that form are a number of categories of deductions; the instructions explain every category pretty well.
The second is a book titled "What the IRS Doesn't Want You to Know." It explains, pretty well, the enforcement procedures of the IRS.
To answer the specific ... fines, penalties, judgments, and the like are generally NOT deductible.
