Some dogs have real problems with brusing and combing them, depends on their fur they have. Some have real bad tangles.

Our female dog didn't like the brush that was used on our golden retriever. We used a simple comb, no, she didn't like it.
We tried everything and then we popped into this pet place and said we have a jack russell that doens't like the other brushes and combs we have. She told us to use this one that is like a curry brush and she loves it, you do it in circles and doesnt' pull her or hurt in any way. It brings up all that dry stuff they get and the fur. And she sits there and wants lots more and the male gets jealous and pushes in there and demands his time too.

yes, he should be taken to a groomer and professionally groomed and fur trimmed to nice length and nails clipped and the whole works. then you can work on him as the fur won't be long and pull and if he's brushed daily he will slowly get used to it and won't tangle.
My dad used to spray something our golden retriever as he would be a mess underneath the tail part and that would be so tangly.

Yes, he needs to be groomed.

We did that with our springer spaniel and what a difference that made and its makes them feel so good.

Brushing should be like a message, make them feel so good. Talk to him while you are doing it and give him treats along the way and hope it works out for you and him.