I would start with some ground rules:
You pick up your things. If you don't and I have to pick them up, I get to decide what to do with them, including trashing them or selling them. If I trash or sell something, I will not replace it. You can get a job and buy the item yourself.

You do your chores. If you don't do your chores, certain basics and/or privileges are removed. For example, if you don't do your chores, I don't do your laundry. If you don't do your chores, I will not cook dinner for you. If you don't do your chores, I will not drive you to activities, etc.

Wi-Fi password changes daily. You have to complete homework and/or chores to get today's password.

Etc.

If that doesn't work, there is the tough love method. All possessions including furniture, bedding, clothing are removed and he will have to earn these back by following rules and doing chores. Here's one woman's solution:

https://www.huffingtonpost.com/entry/moms-tough-ultimatum-for-disrespectful-13-year-old-goes-viral_us_55fad07fe4b0fde8b0cd2702

This went viral and some criticized her for her parenting. She later wrote this follow-up:

https://www.facebook.com/notes/heidi-johnson/an-explanation-to-the-open-letter-to-my-son/10153596019924869

Sounds like OP may need to move to the tough love stage.

Anonymous wrote:I read that book. I've been trying to be flexible, but he pushes until he basically decided that he doesn't have to do anything I've asked him to do. Chores, speaking politely, discussing plans, going to bed at a reasonable hour etc etc etc. He seems to want/need boundaries, but I'm having trouble setting them largely because now that I have his phone, I don't have any other leverage.

I think using leverage to do any of the things that, basically, allow family to function is a bad idea from the beginning. Out of the things you mentioned (or didn't mentioned), what bothers you the most? Why is the struggle about picking up some thing, that, literally, takes you a second.

I read that book. I've been trying to be flexible, but he pushes until he basically decided that he doesn't have to do anything I've asked him to do. Chores, speaking politely, discussing plans, going to bed at a reasonable hour etc etc etc. He seems to want/need boundaries, but I'm having trouble setting them largely because now that I have his phone, I don't have any other leverage.

Eating out, WiFi, nice clothes, electronics, allowance and even the door on the bedroom is a priviledge. It is easy to take them away if they do not behave or are respectful.

Anonymous wrote:Don’t flame me, but my teen has started being openly defiant. I’ve already taken away his phone. That’s really the only thing he cares about. Now that I have the phone, I have no other leverage. For example, I ask him to pick up something that he left in the living room and he says, “No. It’s ok. I don’t need to do that right now.” And I say,”Yes. You do. I’m telling you to do it now.” And he just sits there. What do you do?

OMG OP listen to me, please--I had this issue. Don't go head-to-head like this! It totally backfires and GETS WORSE! (Trust me, I know). DCUM saved me, and here is my chance to pay it forward....buy this book, "Yes, Your Teen is Crazy!" right now on amazon.

And the short story is you are still a good parent if you let him leave his crap all over the house and say nothing, and pick it up yourself when he's not around. (I know, sounds totally wrong, but THIS will work. It's counter-intuitive)

OP, what else he is defiant about? The example you gave is hard to judge without the context. Not picking up stuff is nothing if everything else is good.

Anonymous wrote:

Anonymous wrote:When my teen leaves too much stuff lying around, I give a deadline for when it has to be cleaned up or I will clean it up and if I clean up it gets thrown out and my teen knows I mean it.

She left a new pair of sandals lying around and she thought for sure I would just put them away for her. Nope. I put them in the donation bag and donated them. No reminders, no yelling, no fussing on my part. I had given her the deadline and she didn't put them away so I reasoned she didn't want them or care about them. She had an old pair of sandals she could wear or other shoes or she could earn money and buy herself another pair. Yes, it hurt to donate a brand new pair of shoes but she now knows I am serious.

Who pays for the stuff you donated?

Yeah. This just seems like throwing money away. I might put them away and make her earn them back.

Anonymous wrote:When my teen leaves too much stuff lying around, I give a deadline for when it has to be cleaned up or I will clean it up and if I clean up it gets thrown out and my teen knows I mean it.

She left a new pair of sandals lying around and she thought for sure I would just put them away for her. Nope. I put them in the donation bag and donated them. No reminders, no yelling, no fussing on my part. I had given her the deadline and she didn't put them away so I reasoned she didn't want them or care about them. She had an old pair of sandals she could wear or other shoes or she could earn money and buy herself another pair. Yes, it hurt to donate a brand new pair of shoes but she now knows I am serious.

Who pays for the stuff you donated?

When my teen leaves too much stuff lying around, I give a deadline for when it has to be cleaned up or I will clean it up and if I clean up it gets thrown out and my teen knows I mean it.

She left a new pair of sandals lying around and she thought for sure I would just put them away for her. Nope. I put them in the donation bag and donated them. No reminders, no yelling, no fussing on my part. I had given her the deadline and she didn't put them away so I reasoned she didn't want them or care about them. She had an old pair of sandals she could wear or other shoes or she could earn money and buy herself another pair. Yes, it hurt to donate a brand new pair of shoes but she now knows I am serious.

Anonymous wrote:None of this stuff works. I’m at my wits end.

He is trying to push your buttons and you are letting him.

Why is this a button for you?

OP, I don't have any answers for you. But I did want to say that some kids are so easy - I have two like that. Everything that others mentioned would work but likely wouldn't be necessary. And I have a third one that is sometimes like yours. To complicate things, my son has mental health issues and it's often hard to tease out what is mental illness and what is asshole teenage behavior. Regardless none of the things people mentioned would work and if I push too far, he'd just leave or do something stupid like try to kill himself. I could never take his phone because sometimes that's the only way I can track him.

With him, we manage by reducing the expectations. I would never have asked mine to clean up his mess because I knew I could t enforce it. I only ask/require things I know I can make happen so I don't lose credibility. I also have my son in therapy and receiving medical care. His doctors and therapists have no other suggestions.

BTW, my sons mental illness only started to show up around age 15.

Did you sit down and ask him why he is acting this way?

And what 8:29 said

None of this stuff works. I’m at my wits end.

I would talk with him about mutual respect, rules of the house, rules for how we treat our fellow human beings, particularly our parents. From your description, it is hard to figure out if you are describing a sociopath, or just a teen challenging your authority who needs a firm hand from you and consistent discipline, but would be reasonable in agreeing to basic human interactions. If the latter, that kind of answer from him would get a huge response from me -- not just taking away the phone, but a stern response, a discussion about how we can't live our lives that way, it's not a democracy and he's not my roommate, then a taking away of all privileges and help from me in any aspect of his life until he treated me with respect. I wouldn't let him leave for school without doing what I had asked. He would then have to walk to school and take the consequences for being late. Does he care about good grades, getting into college, the reputation he has with teachers? For my kids, all that would be on the line and I would use it all as leverage if I had to. But this would make sense for my kids, because it would be a (extreme) continuum of the parenting that I have done all along, so if they acted as your son is acting, it would be such a huge break in our relationship that it would deserve either huge psychotherapy or huge discipline. But really, my kids don't act like this at all, so I have no context for what you are describing, so sorry if this is not helpful.

Read Positive Discipline for Teenagers. I have found giving them a little more control and input makes boundary setting (and keeping) much easier.