Am I entitled to this money?

I wouldn't work for that scum bag. They have to offer a benefits package but you'd still have to pay a premium.

Ask him how much he was expecting to pay for the medical insurance,

and how much it will actually cost.

Then you could offer to pay the difference.

... Then ask if he would pay "the expected amount" towards medical insurance of your choice.

However it sound like you have a difficult time communicating with him.

maybe he does that on purpose, if so you probably won't be working there very long anyway.

Not if it wasn't in the company handbook you received when you started there. An employer can "promise" any benefits they want, but unless it's on paper, they don't have to stand up and actually do it.

This actually fits more into the realm of lending money to someone. If you don't sign a sheet of paper saying they owe it to you, then you might as well kiss it goodbye. Same thing applies here.

No, you are not entitled to ask him for money for insurance. Employers are allowed to change or even eliminate the benefits offered to employees. The employees are entitled to leave the job if they are unhappy.

I would talk to him about a raise since he is not providing benefits but entitled too probably not.

He is not right in what he did but it probably didnt effect you hiring pay.