IF he's healthy for the next 5 years and with a Contender he could do it.
I like that thinking, it makes me think he may want to actually Stay with Houston, I think he's a FA at seasons end.
As for never seeing another 300 game winner, its very possible, seeing the Starters never go long into games anymore, could go in your favor or against you, depending on who they determine should get the win.
Never really understood that entirely either. How they determine who gets the Win when multiple pitchers pitch .
I've seen a guy come in in the 7th inning, pitch to 1 hitter and end up with the Win.