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What do sky divers have in common with MLB General Managers? Why would Tiger Woods make a good pitching coach? Why are middle relievers better than ace starters? This talk will answer all of these questions and suggest a central theme – the tectonic plates that underlie modern pitching have shifted and nobody has correctly exploited this shift. Further, the team that understands this shift and adopts a disruptively different pitching staff will win more games. This talk will first discuss applications of economics, behavioral finance, and portfolio theory. The talk will then propose the “Paired Pitching” model of pitching staff construction, analyze what effects various manifestations of Paired Pitching would have on wins, and will close with an examination of empirical evidence that a rotational pitching system is indeed sub-optimal.