Legal Question in Business Law in California

Of course he can have a different benefit plan. No he can't legally defraud the IRS.

And, to top it all off, she gets paid more than you do! The injustice of it all. You could always snitch off your boss to the IRS or, if you are feeling really malevolent, Microsoft.

I know that an owner/CEO cannot have a 401(k) plan that is significantly more beneficial than the plan offered to the rank and file without some tax-liability consequences. It is not prohibited per se, but the tax laws make it something most CEOs would want to steer clear of. I am less sure that similar rules apply to company-paid health insurance plans -- so I will only say that the CEO sure can have a better health insurance plan than the rank-and-file, but there might be some loss of tax deductibility that would be unfavorable to the big shot.

As to the second question, taking money that is not a salary that will be reported on a W-2 or a dividend that will be reported on a 1099-DIV is tax evasion.