When is Enough Enough?

L. is one of my dear, sweet, wonderful mentees. He is very smart and doesn't have much trouble understanding the content in class. He's very curious about how things works and loves anything mechanical. However, L. has a long history (his 9th grade year felt like an eternity) of not producing ANYTHING. At the end of the semester last year, he was literally still doing assignments from the first day. He went weeks, maybe months, without turning in a single English homework. In the first 4 days of classes this year, he was already missing 10+ assignments. Today in Spanish class, the entire class cheered because he had his homework packet out; even though it was blank, just not losing it was a major accomplishment.

As his mentor, I have taken an unofficial oath that I will love and support him and do whatever it takes to get him to eventually get him into college. When I say whatever it takes, I mean pretty much everything. Our school already has a lot of support structures set up--office hours, after school homework jail for kids missing assignments, month long extra classes at the end of each semester when kids can make up work, etc. Last year as L.'s teachers, we had MANY parent meetings, made him stay after school on Fridays, and even pulled him out of his elective class so he could spend time making up academic work. I remember him running away from me and trying to hide under a table because I was trying to walk him to office hours. At any other school, there's not even a remote chance he would've made it to 10th grade.

This year is not going much better, but I finally found something that sort of works: during his study hall period, which coincides with my prep time, I have been pulling him out of study hall, taking him to an empty room and sitting next to him to keep him focused. He doesn't really need much help; like I said, he's very smart. Rather, he needs someone to be there to remind him every 5 minutes that he needs to get back to work. He also needs someone who will put up with his constant whining about how boring everything is, how much he hates it, and how much he doesn't want to stay after school that day. I spend this time telling him trying not to roll my eyes and then organizing his backpack so he'll quit losing papers.

Like I said, this only sort of works. He's gotten a lot of work done with me, but he hasn't actually turned most of it into his teachers. He keeps telling me he forgot, which I completely believe. I am trying to teach him responsibility, so I have walked him over to his teachers on multiple occasions. Here is an exchange from last week:

Me: "Let's go, you need to show Ms. R. that you finished this."
L.[imagine a very whiny voice]: "I don't want to."
Me: "Come with me. Let's go find Ms. R., I think she's in her office."
L.: "Awww, I'm too lazy."
Me: "Too bad, let's go."
---We walk over to Ms. R.'s office. She is sitting inside and we can see her through the window.----
Me: "L., tap on the window so she knows you're here."
[L. leans against the wall, hiding from the window. I tap on the window for him.]
Me: "Ms. R., L. has something he'd like to show you."
Ms. R: "What is it, L."
[Saying nothing, L. hands her a crumpled paper]
Me: "What do you want to ask her?"
L.: "Here's my assignment."
Me: "What do you need her to do for you? What do you need to ask her?"
[L. looks away from us. There is a long pause while I gesture at him to talk to his teacher]
Ms. R.: "Would you like me to sign this off for you?"
L.: "Yes."
[L. gets the signature to show it's complete, and then mopes away]

I am at a loss about what to do with this kid. What else should I do? What else can do? I'm already giving up a full prep period every day, and it's only having a marginal effect. I can only spend so much time walking him from class to class finding teachers and coaching him (unsuccessfully) on how to interact with them. If I keep organizing his binders, it's hard to say whether he will ever follow suit, but he definitely won't follow suit if I don't do it. I am in constant communication with all of his teachers--mostly because about half of them come to me everyday to tell me what he DIDN'T do in class. I've talked to his parents, in person and on the phone, already at least three times this year. I do love and support L., both because it is my job and because he's generally a sweet, funny kid, but he's driving me out of my mind.

Where do I draw the line? When is it sink or swim time? I'm always been uncomfortable with the idea that some kids "need" to fail because what does that even mean? He has already experienced so much failure in the past year with every test he's gotten back, every time he's chastised for not having his homework, every Tuesday and Thursday when he has to go to homework jail, every time skips out of office hours when he knows he shouldn't. Would the massive failure of repeating a grade be the thing to teach him the responsibility he so severely lacks? At this point I have no idea. But I do know that unless someone comes up with some brilliant plan, it's going to be a very, very long year.