Pete you have two problems and I am not sure you can fix either of them very easy. The one problem is obvious, the teenage boy. The second is your wife that is enabling the teenage boy in his bad behavior.
I would ask the wife if she wants your son to be a failure the rest of his life because she is teaching him bad habits that he may not grow out of as he gets older.
If I remember right, this is the kid that thinks he is the next NFL super star??? Well he is going to be lucky if he can even get a job flipping burgers as an adult with ZERO education.
Sounds like you need to keep the son's cell phone shut off and the wife shut off from the money. My brother had to get a separate checking account that his wife had zero access to. She had health issues that made money management hard for her to do. If I remember your wife has some issues too. So limit her access to money then she can't bail out the kid.
I am not saying this to be mean but I would bet that the $50 for the cell phone is not the only money she is spending on him. HE IS FAILING in school, so I would provide him nothing but food and shelter. Anything else he wants let him earn it himself.
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