It hasn't felt like Luffy has deserved anything in a long time, since at least Whole Cake Island where his victory didn't feel earned or believable at all.
The amount of plot armor and exterior help that Luffy relies on has only increased with time, even more post-timeskip, and the fact that he doesn't have any competence other than fighting whereas Roger at least had some scholary attitude and interest in the Void Century doesn't help.