Jon Lester was a starting pitcher who spent most of his career with the Boston Red Sox and Chicago Cubs.
Lester was a common topic on the podcast due to his inability to throw a pickoff to first base. His throws were off the mark, sometimes wildly so.
- Episode 650: Lester's second start after it became widely known that he can't throw to first.
- Episode 653: What would happen if everybody ran on Jon Lester?
- Episode 655: Lester faces the Reds and Billy Hamilton. Ben and Sam wonder what will happen.
- Episode 656: The showdown did not materialize: Billy Hamilton didn't start. Lester's two pickoff attempts did not go well. Ben and Sam come up with the least damaging yip.
- Episode 667: Lester has the second-worst "takeoff rate" (steal attempts allowed).
- Episode 695: Billy Hamilton stole three bases on Lester, plus two additional, for a total of five in one game. No Met has stolen five bases all year.
- Episode 702: Lester got his first hit of the season, but has not attempted a pickoff since opening day.
- Episode 717: Lester attempted a pickoff! It did not go well.
- Episode 718: (Listener email) When would it be worth playing the first baseman behind the runner, sacrificing holding the runner for increased range?
- Episode 726: Lester throws out a runner trying to steal second. Not a pickoff.
- Episode 830: (Listener email) Is it worth it for Lester to have a personal catcher (David Ross).
- Episode 864: Jon Lester fielded a bunt, but the throw to first was horrible.
- Episode 900: Listener email asks why people aren't stealing off Lester.
- Episode 931: Lester tosses the ball softly to first, but the runner takes off and steals second. Sam and Ben marvel at the huge lead the Brewers took on Lester.
- Episode 967: The Dodgers took very long leads but did not make many steal attempts. Sam compares this to the Brewers, who stole five bases in four innings. Are his problems actually good for the Cubs, because teams are trying too hard to take advantage of them?
- Episode 969: (Listener email) If Lester picks off a runner to clinch the World Series, would the long con have been worth it?
- Episode 971: (Listener email) Should Javy Baez move to first base when Lester is pitching and there's a runner on first?
- Episode 1163: Willson Contreras tells how he got Lester to pick of Tommy Pham at first base.
- Episode 1187: Lester has begun practicing a bounce pass throw to first.
- Episode 1200: Lester used a bounce pass to get Ryan Braun trying to steal third.
- Episode 1204: (Listener email) Consider a pitcher so bad at pickoffs that runners could steal second and third base at will. How good would he have to be to remain a viable major leaguer? (Answer: As good as Jon Lester.)
- Episode 1234: Nate Freiman talks about playing with Jon Lester.
- Episode 1262: Jon Lester pickoff.
- Episode 1367: (Listener email) Could Jon Lester bounce his pitches into the strike zone?
- Episode 1797: Ben and Meg reflect on Jon Lester's career after he announces his retirement. Ben regrets that the thing he most remembers about Lester is not his awards and accomplishments but his inability to throw to first base. Ben and Meg continue to riff on the topic, including why teams didn't run on him more.