He's not afraid to go in there and lounge or play, but if I put him in there when I leave, he shakes and starts having a barking fit. We finally got to a point where we have the entire kitchen 'puppy proofed', so we let him have free roam at bedtime which works out pretty good since he's tired and doesn't cause too much trouble.
I guess it's easier just to explain his 'routine' and maybe it will be easier for suggestions.
bedtime- we have a huge kitchen(2 large areas)...he has 2 beds, one in his kennel and the other at the other end of the kitchen. Both doorways are blocked off with gates and he has his potty pad over in the corner.
when my husband wakes up in the morning, he lets Turky eat/drink/do his 'business' and then he brings Turk in the bedroom and puts him on the nightstand before he leaves so Turk can nap while I catch my last couple hours of sleep. We decided to do this because this seemed to be the time that Turk was getting into the most trouble. (after dh left and while I was sleeping) Little turd decided to eat the trimwork around the sliding door.
late morning/early afternoon- Turk roams and I try to get most of my business done in the kitchen area. I always make sure to play with him during this time before I leave for the day(and I make a point not to be gone too long). Turkleton goes into his kennel just for those couple hours and immediately he starts getting shakey and nervous. I turn on the radio to give him something to listen to and a treat trying to reassure him he's okay while he's in his cage, but as soon as I get to the garage I can hear him barking his little head off.
By the time I get home, he has TRASHED his kennel. He shredded and pulled the stuffing out of his new bed and ruined the rug that I put in there. I feel so guilty, but I can't leave him out of the cage during the day because he still can't be trusted.
Any ideas/suggestions on how to get him more comfortable in his kennel while we're gone during the day?

I do think there's an issue of anxiety, but part of me thinks he's also having a tantrum. I can't just keep buying him new beds and rugs. I'm doing everything I can think of to make life easy as possible for everyone, but I'm at a loss on this one...