Blyleven
I think Blyleven should make it. 287 wins is impressive, in any era. He lost a lot too, but he played on a lot of weak teams. Tracking his career, it seems to me he was usually scheduled against the other team's ace. Thus he came up short on the winning % despite some good stats. If he had found a way to win only 13 more times in 18 years, he would be a sure thing with 300.
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