Baseball: 511 career wins. Cy Young was such a dominant pitcher in the late 1800s and early 1900s that the award for year’s best pitchers is called the Cy Young Award. The dude won 511 games—nobody has won more than 300 in decades. That’s because when Young pitched, pitchers pitched every other game or so, as opposed to today’s five-man rotation. Pitchers today have less chance to ever amass 511 starts, let alone wins.