Why not? if he's capable to lead his team and can still produce those numbers or more larger than what people expect then its fine.
But question is does the new management would allow it? knowing that they know Lillard might be injury prone in next following years. Well Maybe we could see all of this once he gets back on the roster if he could still able to lead Portland the same as before.
I don't have any big expectation for Portland but let see what they can do next season.
For now, I believe Portland using him again as the main guy on their roster because that’s the only reason why would a team will re-acquire their main star after trading it.
I don’t know the full scope how deep their roster but for sure they already acquired a lot of young talent and the missing pieces is a veteran star player that has a potential to explode on any game.
Assuming Portland indeed have deep roster including bench. With Lilard help will surely gives them better position in playoffs