You could make the argument that Reggie Jackson might be the most clutch hitter in the history of baseball. After all, this is a man famously nicknamed “Mr. October” for his clutch hitting in the postseason, as a member of the Oakland Athletics and New York Yankees. Jackson helped New York win four American League East divisional pennants, three American League pennants and two consecutive World Series titles, from 1977 to 1981. He also helped the (then) California Angels win two AL West divisional pennants in 1982 and 1986. Jackson hit three consecutive home runs at Yankee Stadium in the clinching game 6 of the 1977 World Series.