At the end of the day, Pickett is one of the luckier quarterbacks to have ever played the game. Mid-round talent who, in his 5th year of college, latches onto a first-class receiver, along with having an old drunken OC who gets his jollies off with throwing the ball even when you're up by 60 points on an FCS team in the 4th quarter.
Combine that with a historically awful QB draft class, and now all of a sudden teams and draft analysts alike are convincing themselves this dude might be a first rounder. Now, not everyone is havin' themselves some of that Kool-aid. Certain draft analysts wouldn't budge on calling him a mid-round talent, and we saw 19 guys come off the board before him, which almost never happens in such a QB-starved league (I mean, look at some of the quarterbacks taken in the top 19 every year). But, eventually, a GM on his way out gets ultra paranoid that his legacy will be akin to what the Steelers didn't do in 1983. So they take Kenny.
Now, you may say the circumstances were not ideal (they seldom are for quarterbacks in the NFL). But the fact remains that, because he was a first round pick, not only has he already banked more money than most of us will ever make... he also received opportunity after opportunity to show that he should be a starting quarterback in this league. Had he been taken in the 4th round, he'd have always been doing what he's doing now and no one would have thought anything of it. But, boy oh boy, did the stars ever align for Kenny Pickett.
I mean, yeah - plenty of teams that needed a starter this season could have acquired him for basically nothing and elected not to, so it's possible that his luck has ran out. But what a run if has been. And he's still cashing those first round checks.