President Barack Obama read Spider-Man and Conan comics when he was younger, and could still quote from them. So when he became President, marking the first time a black person had achieved that role in the USA, Marvel Comics decided to also mark the occasion but including a short story featuring Obama meeting Spider-Man.
Spidey Meets the President! appeared in The Amazing Spider-Man #583, was written by Zeb Wells, with art by Todd Nauck and Frank D'Armata, and published on the 14th January 2009, a week before Obama's inauguration.
It sold really really well, with lines around blocks, especially for the Obama cover that appeared on a quarter of all issues.
So Marvel put out a second printing only a week later, the day after the inauguration, with just Obama on the main cover. That sold even better. The comic went through five printings in total, topping 350,000 sales.
No Donald Trump eight years later though. He was always more of a DC Comics guy, anyway.
Amazing Spider-Man #583 now sells for $4-6 for first print standard cover, but from $50 to $100 for the first print Obama cover–unslabbed.