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.