He won three Cy Youngs, one MVP, a Gold Glove, a Roberto Clemente Award and the 2020 World Series. Despite pitching for 18 years, Kershaw didn’t face the Boston Red Sox in the regular season until this season. Story continues below advertisementThe southpaw started game one and game five of the 2018 World Series, losing both games. With 3,039 career strikeouts and 222 wins over 2844 2/3 innings, Kershaw will be heading to Cooperstown when he’s eligible for the Hall of Fame. First, he’ll be part of the Dodgers’ postseason plans when they begin postseason play at the beginning of October.