How do you punish the kids that has figured out I can't 'make' him do anything?

My son is 7 and hard headed as hell! So he has always been 'challenging' but it is getting worse. We have always done time outs with him but he doesn't care. so let's say I ask him to carry his toys upstairs. He say's no. I tell him to sit in time out. He does no problem sometimes other times he screams I will get to that.... I tell him again to clean up the toy. He say's ' no I'll just sit in time out and will just sit there smirking at me. the toy will still be there at dinner. I tell him no dessert until the toy is picked up. He say's 'fine. I don't like dessert anyway' I finally pick the toy up put it in his hand and tell him to take it up. He drops it. I then put the toy in the trash. He says ' he doesn't care' He does this at school to! He will act up. They send him tot he hallway and he will play in the hallway knowing he is getting out of the work. He know no one can literally force him to do anything. He is happy to avoid the work by sitting in the office or time out or on the steps. I tried for while taking all his toys away. Like ALL of them. He did not care! And he isn't all passive all the time. He does weird things to. Like I caught him climbing out of his bedroom window when he was 6. I had to nail it shut after he did this 3-4 times in a week He smears tooth paste on the mirror for fun. I have to keep it out of reach. Soap also. And toilet paper. He has to ask me for toilet paper because he will put it int he toilet or sink or tub. He will refuse to take baths sometimes just because he knows I can't pick him up and put him in the tub and wash him. He knows if he screams and keeps jumping out it literally will not work. Sometimes I will send him to his room as a time out because he will sit on the stairs and scream- refusing to sit on the steps. He will then go in his room and scream bloody murder for EVER. I just don't know what to do. Nothing works. He knows I can't hold his hand and force him to do what he doesn't want to do. He knows how to get out of things by getting in trouble. ANY ideas?

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