Okay, I've got a challenge for the Italian Renaissance experts on this here forum.
Have a timeline were Dante, he of the Divine Comedy, become the Pope, preferably with Dante still writing the Divine Comedy. I mean, if the Borgias could become Pope, why not him?
After the defeat of the Ghibellines, wasn't Dante strongly anti-Rome, which led to his exile? I guess the POD would have to be in his youth: He takes up theology and goes in for ordination. He moderates his strongly Florentine stance, or at least - believes Florence and Rome should be allies.
The problem is how to get a Papal election AND have Dante be a contender. Boniface VIII has to die earlier, and Dante has to represent a faction that Rome wants to be allied with. Can the Florentines set up a new "Lombard League" for dealing with Henry VII's HRE invasion forces?
The problem is, if he becomes Pope, his views will change sufficiently for the Divine Comedy to be very different from OTL - maybe not published at all.