[bellanrocco]

I would say to start off slowly. Lay treats or his favorite toy inside the kennel, and leave the door open. When he goes in, praise and pet him. When he goes in on his own, give him a treat. This way he doesn't see it as him being punished.
I actually have not used a crate or kennel. My husband recently bought a little play yard (it's like a gated enclosure) that's big enough for Rocco's food and water bowls, toys, bed, and three pee pads. Because we are gone for so many hours of the day, this keeps him from having to remain locked in a kennel or crate for too long and at the same time prevents accidents.
I would keep trying, don't give up!