Many of those photos are just the getting posed photos of them standing next to each other but it seems that he and JFK Jr. were at the game together and friends, I think, that is the impression I got from Snopes.
I think you are underestimating the vast and enduring changes Reagan brought to America and the world, and Reagan did it before talk radio, before Fox, before we even knew that Republicans could have a Congressional majority, and before the internet, and before there was any real conservative awareness or language among the population, he did it pretty much alone in a sea of liberalism and liberal mass communication and all of one point of view.
In 1980 America practically no one would speak up as a conservative or admit to being a Christian at cocktail parties and at the water cooler, no one among the general public of the middle and upper middle class.
I think you overestimate the permanence of the changes Reagan made. With Rat Land candidates we are always one to two administrations from a permanent bureaucratic dystopia. In this modern InfoAge you don’t need a North Korean 1984 style government using terror to control people. You just bury them in a life of personal ineffectual greyness. Give them enough to keep them docile. Today you would probably get a plurality to agree with that life if you put enough smiley faces on it.