Seems to me like Scheif (or his agent on Scheif's behalf) asked to have his roommate included in the deal and the Chef said no, it's double the work. But is it really? If they're eating the same thing it's just double the portion, which isn't a crazy amount of extra work. Refusing to do so, IMO, would be insubordination and grounds for dismissal with cause. Scheif would be covering the cost of the extra food. Would the extra $5,000 not be enough to cover the workload of preparing/ordering a second portion?
We don't know the whole story here, just what was filed in court but to me it looks like the termination was justified. If he was supposed to provide Benefits but didn't that may be another story and he may owe this guy another $5-$10K depending on what was agreed to be in the benefit package. What services, limits, deductibles, coinsurance etc did they agree to? Was life insurance and LTD to be included? Did they even talk about what the benefits would look like? It could be the Scheif was just self insuring his benefits and would reimburse him for any medical expenses he incurred. If he was healthy and didn't have any medical expenses, Scheif wouldn't have had to pay him anything. There's lots of leeway with "Benefits" and no 2 packages are the same.
It's been a year and a half since he was terminated, so IMO why wait so long to do anything if you had a legitimate case. Feels like a desperate cash grab.