Earlier quoted context omitted.
The 1099 versus W-2 gambit is dangerous. He could, in principle, claw back the entirety of the 1099 payments, including whatever you paid on as taxes, then adjust them to a W-2 and pay you back less W-2 taxes. You'd then have to wait until the next tax cycle to get a government refund on the 1099 taxes. Retroactive reclassification of money is a dangerous game unless you have big cash reserves and lawyers of steel. T…
Actually, the IRS has been cracking down on 1099 abuse. So, he doesn't necessarily need to get a lawyer, he could possibly just notify the IRS and let them come in with lawyers. I agree with you that using the law is always a bit of a gamble. But the mere threat of calling in the IRS might be useful.
Basically the IRS considers the employer guilty unless they can track down the contractor/employee and extract paperwork from them, even though the IRS already possesses the documents that conclusively prove innocence. I'm actually mildly impressed nobody has truck bombed them yet. Crazy as he was, the airplane dude had a point.
The lesson for contractees is that you pay estimated taxes for your 1099 contractors. If they have deductible expenses, they can take it up with the IRS on April 15.