Ryan does this because he can. He's trolling and doing a damn good job at it.
I'm the same age, played a bunch of sports against him, and yes he was a unmitigated tool in HS. I was on the Big Sky HS team (I merely stood and watched) that he lost to in final HS FB game and called us rock pickers. Still one of the best all around athletes I've seen in person at the high school level in Montana.
I got to know him over the years and he's been nothing but personable to me. Worked in two different school districts in Montana with members of his extended family during his descent into addiction and it colored it a bit differently for me.
If you live in glass houses, you probably shouldn't throw stones. I follow him on twitter and he's at least publicly embraced his past failures with a bit of humor. I know that for many when it comes to Ryan, particularly on the western side of the state, they just don't care whether throw aspersions at him for actions that they have/or currently do themselves. Ryan could have stayed in that gutter, but he pulled himself out. To that he should be given credit.
Is he still that tool? Absolutely, and even if was different in reality, it is a simple fact that some Montanans are still bitter about 1994.
But you are getting trolled regardless.