Can I re-lease a truck I am leasing to an O/O?

Okay, this is going to be convoluted but I need someone else's eyes on it.

Let's say I lease-purchase a truck from Ryder or Penske or whomever. I run my own authority and everything, that's all good and covered. Then, an O/O wants to lease onto me, but has super bad credit and can't get their own lease or buy their own truck. Can I lease him that truck, and have him lease onto me? Assuming the company I'm leasing from doesn't care that I'm re-leasing their truck.

I can't see why I wouldn't be allowed to, as long as I don't force him to be leased onto me or anything, but I've been trying to wrap my head around it too long and I don't want to accidentally break the law with the new task force running around.

edit: Okay let's pretend it's a lease-purchase from whomever will let me do so, I was just making up an example haha

 

Really what I want to do is lease-purchase it to him. I know he'll pay me the money and everything, he just has bad student loans. He wants to start his own company and really get into the owner/op stuff so I'm trying to help him out. He'd basically pay me what I'm paying to lease-purchase the truck, and the truck would just be his when it was all said and done, but he could run my numbers while he's getting everything figured out since I've been doing this longer.

 

Honestly? He doesn't want to be a "company driver" anymore and I want to be able to get out of the lease-purchase if he decides he doesn't want to work with me anymore. It kinda feels like the lowest-risk option, if that makes sense? So I lease-purchase the truck for him, lease it to him with the option to buy it whenever, he runs my numbers but gets to feel like he's a cool owner-operator (or, lease-operator really) and can handle his own paycheck without me. If he decides he doesn't like the truck anymore or wants to work somewhere else, I return the truck and there's no real harm done.

 

Hahaha probably, by a landslide. The whole thing is honestly a mess, and I think it's kinda silly for him to up and leave a good paying company gig for this, but since I can only lead the horse to water, I may as well make sure there's water there.