"...and shouldn't even out like that in the short run."
This is a statistically invalid statement. Inferential statistics say nothing about what should happen in the short run. In the short run, there is more variability, but things are still more likely to be close to average than far away from it. We shouldn't expect things to even out in the short run, but at the same time, we shouldn't be surprised if they do.
Now, for the long run. Let's say that in this particular league, Chesbro can be expected to post an OAV of .255. Then, 95% of the time, all things being equal (opposing talent, ballpark, etc), we can expect his OAV after 2100 batters faced (a round number close to the examples above) to be between .253 and .257 (2 standard deviation from the mean).
Across WIS, we seldom can cling to the "all things being equal" caveat. Talent varies widely from division to division, league to league, salary cap to salary cap.
I know this has been beaten to death in other threads/discussions, but thought I'd show the math above again. What strikes me (and I'm assuming what strikes crazy as well) is how similar the numbers are across the board.
Let eastonest beware--he's playing with fire. He's due for a bad version sooner or later!