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(last updated on October 31, 2025)

With the emphasis on power numbers in the modern MLB game, it seems like the art of stealing bases isn’t what it once was. Since the turn of the century, only four players have swiped 70 bags in a season. That pales in comparison to the triple-digit numbers that were seen in the 1980s. However, with the recent rule changes in baseball like the limit on pitcher disengagements, the pitch clock, and bigger bases, stolen bases might become trendy again. Ronald Acuna’s 73 stolen bags in 2023 and Elly De La Cruz’s 67 swipes in 2024 certainly shine a light on this offensive weapon of yesteryear. Shohei Ohtani’s never-been-done-before 50/50 season in 2024 also brings this speedy tool back to the forefront of the diamond. In almost 150 years of baseball, there have been some prolific speedsters, and this list will look at the MLB players with the most stolen bases of all time.

(last updated on November 17, 2025)

The Cy Young award is given to the top pitcher in each league annually. Why call it the Cy Young? Well, this legendary hurler posted 22 seasons in MLB before World War I even started. He is the all-time leader in wins (511), games started (815), innings (7,356), and is third in WAR (163.6). There were also those 14 consecutive 20-win seasons, five of them 30+. The point is that this award is well named for this luminary during the Silent film era.

Since this award started in 1956, 23 pitchers have won it more than once. A deeper plunge shows only 11 men have won it at least three times. That’s who this list will focus on, with the exception of the three modern-day players who have won the award three times (Clayton Kershaw, Max Scherzer, and Justin Verlander). For the sake of posterity, here are the eight pitchers with at least three Cy Young awards.

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