My point was that people shouldn't be shocked, shocked when they get busted for breaking the law.

Of course the fellow wouldn't complain while he was employed. People who live in illegal apartments tend not to complain either, until something goes seriously wrong.

My point is that they aren't breaking the law- until a jury decides they are. They've entered into a consensual agreement for fee-for-work as contractor. Both agree. Both understand. Contractor has certain freedoms (work mostly from home on own schedule, etc.) and certain obligations (pay own taxes, etc).

But a jury decides that the agreement isn't right and that someone was actually an employee. And awards triple damages.

Yes, this can be abused by employers. But even when it's not- it can still give employers heartburn. Anyway, in OP's case it's moot because he was W-9.

  > They've entered into a consensual agreement for 
  > fee-for-work as contractor.

It simply doesn't work like that. A worker isn't a contractor just because the employer and the worker have "agreed"... Both parties must be able to demonstrate that the worker is indeed operating like a contractor. See the IRS rules on this, for example: http://www.irs.gov/Businesses/Small-Businesses-&-Self-Em...

I know. I fully understand this. But certain jurisdictions rule differently. And in MA, it is a serious threat. In OP's case, again, it is irrelevant because he was a w-2 employee.