OHKen hit it------------ I don't know the laws in IL, but in IA, the er should be shaking in his boots-------called risking the farm.

First, you are an employee.........no way around that.  If you want the elements, go to IRS website, but suffice it to say when you do not provide your own tools, set your own hours, do more than minimal work for others, etc------- you are an ee.

Second...........if you were to get hurt right now, any competent plaintiff's attorney knowledgable in personal injury suits, would kill that indep contractor status in seconds, and sue the employer for everything.   If he carried work comp, that would be blocked.

We just had incident yesterday............."Charlie" twisted his back............Charlie is a complainer, etc etc, but we needed a driver, so I kept him on..........shouldn't have, but crap happens.

I called the insurance agent..........hey, what to do?   Turn in a claim?  Charlie says even though was off Wed, will be back Thurs, and chiropractor says "just take it easy".

The important part is---------- the agent's comment----------- turn in the claim.   

Objective is to protect ME...... the employer. 

If the injury comes back to haunt things next year, two years later, whatever, and all the expert witnesses at that time indicate that....well, yes, it COULD HAVE been the result of slipping in the mud two years prior................I, the employer, am screwed...........he (and his attorney) has access to anything I own.   Opening up the claim now limits him to the work comp ins.

So..............if I were in your shoes.............seems to me that opening the conversation with something along the lines of "I was told you are in deep water with respect to our arrangement.........I don't want to see you get nailed just because of avoiding a little paperwork".

Call some insurance agent, or an attorney........find out what the work comp rules are...........approach the problem from the perspective of solving a problem for the er,

and if he is any kind of guy you ought to be working for, he will do it the right way.    Most guys are not knowledgeable of the ramifications, and will get stubborn until someone that they listen to tells them what the real story is, so most likely he will have to talk with his attorney and/or ins agent.............'cause it sounds like his tax person is not giving him the straight dope..........but he has to be informed of the problem, and prodded a little into talking with someone knowledgeable.

Solving his problem for him automatically solves yours.