Is this a usable pattern? (Enterprise application UI)

I'm working on an application that requires a user to assign a year or two to a list of users (there are two year options available. One user can be assigned to one or both years.) And one user per year can be assigned a Leader status. I'm redesigning the current capability, which had a bunch of columns of checkboxes and radio buttons to assign. This also meant the user had to assign years for each row of users and not do any batch assigning. I'm wondering if the pattern I came up with makes a lick of sense, or if there's some other pattern that would work better?

I'm including a quick mockup, but won't provide the instructions because I want to see how intuitive (or not) this is.

(Data and design has been changed from original, but intended interaction remains the same.)