how does swift work

Ask Swift and get it in writing. If they don't offer what you want go some place else.

 

From what I understand they deduct the cost over the first year, then pay it back the second year.
So if you stay with Swift for two years you end up paying nothing for the training.

As to working 'for' your brother, that might make a difference.
Because if you are working for him you would no longer be an employee of Swift.
And if that is the case, you would be on the hook for the cost of the training.

 

You are not locked into a contract to work for Swift for any amount of time. You are, however, locked into a contract to pay Swift back for your schooling. They will work with you on it. Your brother is an independent contractor for Swift and as such can hire anyone he wants to to drive the truck.

 

Well, any prospective hires still have to be approved by the company. I've driven for a fleet owner leased to a 100% owner/op company (CRST Malone), and I still had to go through their application process and orientation. If he's leasing a truck through them, rather than leasing on a truck he owns free and clear, then he's subjected to even more requirements of the company. Even if he does own his truck free and clear, then he's still subject to his insurance policy.. they might not tell him that he can't hire you with no experience, but they'll make it expensive for him to hire you with no experience.