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Jon Lester
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5. Jon Lester

The Chicago Cubs decided to employ the services of the 6'4 left-handed workhorse Jon Lester prior to the 2015 season. This 6-year deal worth $155 million was well worth the investment, as Lester made 171 starts and tossed more than 1000 innings in a Cubs uniform. His physical durability and mental determination made Lester a reliable starter for years.

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His pitching prowess also came up when it mattered the most, as Lester holds a postseason cumulative ERA of 2.51, and 10 of those starts were for the Cubs. Let's just not talk about his appearance out of the bullpen in Game 7 of the World Series.