Do you remember when he talked them into coming in for tires at Monaco 2015 and he went from a sure win to 5th?
Also, let's not even have a discussion on the difference between old tires on a Tilke-ring and Monaco, a track where it's basically impossible to overtake.
Max was probably 2-3 seconds a lap quicker than him and never got close.
And he was on mediums because if it rained, the mediums are better in changings conditions and could buy him an extra lap so they could make an educated decision between slicks, inters, or full wets.
And then on top of that...his tires are gone. What does he want to do? Pit and come out behind Gasly, Bottas, Vettel, and Max on a track where passing is basically impossible?