It will definitely be the N that is protonated, of that there is no question.
The pKa difference of the conjugate acids will be small. Nor, really, are alkyl groups electron releasing, as such.
The N, being more electronegative than C or H, will have more electron density on it in the tBu species, for the simply reason that there are more electrons to draw to it. Hence, the second is most basic.