To the best of my knowledge, the IRS has avoided the specter of regulatory capture simply because there is no single industry big enough to take down an agency

To the best of my knowledge, the IRS has avoided the specter of regulatory capture simply because there is no single industry big enough to take down an agency with such a broad mandate. Most of the industry-specific loopholes that the IRS does administer are not carved out by the IRS itself. Rather, those are the product of lawmakers making deals in Congress. And of course, the IRS isn't generally telling people what they can and can't do in the marketplace. They're just saying that, regardless of what you do, taxes must be paid. In other words, I suspect your tax lawyer friend is not a very good example of the problem see with captured regulators in the financial industry, where the balance of power between the regulators and the "regulated" is practically inverted.