From the historic dominance of Clayton Kershaw to the epic collapses of the Milwaukee Brewers and the Atlanta Braves, it’s been a memorable 2014 MLB regular season.

Simply put, there have been major winners and serious losers from all around the league. Jon Lester falls onto the right side of that equation thanks to a brilliant second half, which has set him up for a winter payday. 

There’s even room on the list for an ace and an executive who could still end up in either the winner’s or loser’s camp. 

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