The problem is not just that the law is overly complex. The problem
is also that we change it all the time.

We [Judges of the U.S. Tax Court] have from time-to time complained
about the complexity of our revenue laws and the almost impossible
challenge they present to taxpayers or their representatives who
have not been initiated into the mysteries of the convoluted,
complex provisions affecting the particular corner of the law
involved. . . . Our complaints have obviously fallen upon deaf
ears.

[T]wo things are abundantly clear. One, tax simplification is
desperately needed. Two, any effort is likely to be an unmitigated
disaster.

Lawyers are trained to ask questions and raise issues about
everything. This is especially true for tax lawyers, who tend to
approach issues from a more analytical perspective. The result is
that in many commercial endeavors, tax lawyers are likely to raise
a number of perplexing, and often unanswerable, tax issues. Their
clients may be presented with dense explanations of confusing
statutory rules implemented by sleep-inducing regulations. The
issues may be publicly vetted at tax seminars; then “fascinating”
law review articles may be generated and even treatises may be
published with unlimited footnotes raising eternal questions. This
is the state of play that keeps the tax bar occupied (and for most
of us, happy) day after day, year after year, and, as it has turned
out, decade after decade.

All the Congress, all the accountants and tax lawyers, all the
judges, and a convention of wizards all cannot tell for sure what
the income tax law says.

Every stick crafted to beat on the head of a taxpayer will
metamorphose sooner or later into a large green snake and bite the
IRS commissioner on the hind part.

Most tax planning adds little or nothing of worth to our
society. . . . Tax lawyers perform a legitimate role of
interpreting the law, instructing clients in the sometimes bizarre
requirements the law imposes to get a given tax treatment, and
planning transactions to avoid the occasional warts in the
system. It is an honorable profession, and I am a proud member of
it. But let’s not kid ourselves that most tax planning is
productive.

The problem with practicing tax law is that the general rule never
seems to apply to anything.

Lots of people talk about simplifying the tax law. And lots of
people agree that simplifying the tax law should be a policy
priority. But the problem is that simplification is complicated,
and it is politically dangerous work.

Complexity does not enter the tax code so much out of malevolence
as through misguided reform efforts and excessive demands made on
tax laws as the vehicle for implementing public policy.

Transfer pricing may be an art rather than a science, but why does
it have to resemble Pablo Picasso?

The tax bar is the repository of the greatest ingenuity in America
and given the chance those people will do you in.

There is an ancient belief that the gods love the obscure and hate
the obvious. Without benefit of divinity modern men of similar
persuasion draft provisions of the Internal Revenue Code. Section
341 is their triumph.

A society which turns so many of its best and brightest into tax
lawyers may be doing something wrong.