What we did with Roxy when she was a pup was throw treats in there and let her go in by herself, we also fed her in there too. Dont just wait until he gets in a close the door on him! It may take awhile but let him go in and out on his own will. Then when he gets use to it you can start closing the door for short periods, then opening it again.
The crate gives them a sort of den like feeling and to some dogs a sense of security(their OWN place to go to get away from everything).
Just a reminder though........DO NOT let him out when he is throwing a fit lol Training will only backfire! Atleast it did with Roxy!!!!!! Just ignore him.
Matt, I got Samson also when he was 6 and he had never been crated. His foster mom introduced him to it and I continued using a crate for a long time, due to separation anxiety...I found for Samson, putting a few treats in there helped, and using treats to get him in. Fill a kong for him and give him that also, keeps them busy for awhile ....Samson does not like the crate, I'll be honest, so he never got the concept of it being a retreat...Now Angel is incredibly good about being crated.. I stick her bear in there and just give her a bit of a nudge and she goes in, Very little fussing...And definitely, if they start to fuss, ignore it....That just feeds into their getting attention...
Just go slowly. Introduce him to it with LOTS of praise and only when you're there for a while, then work up to small trips out of the house with him in it. Another thing I would do is to make it nice and comfy in there for him, keep the crate in your bedroom and make him sleep in it at night. This will reinforce to him that the crate is a nice place to go in and take naps in.
Oh Matt!!!!!!!!!!!!!! I wanted to tell you before you go pay $100+ for a crate at PetsMart or Pet Country go to the Tractor Supply they have them on sale for $60!!!!!!! Yes thats for the big ones too! They also had dog beds on sale for $9 if there are any left! They seemed good too.