Waddell was a remarkably dominant strikeout pitcher in an era when batters mostly slapped at the ball to get singles. He had an excellent fastball, a sharp-breaking curve, a screwball, and superb control (his strikeout-to-walk ratio was almost 3-to-1). He led the major leagues in strikeouts for six consecutive years.

Born in 1876 outside of Bradford, Pennsylvania, Waddell grew up in the country. Biographer Alan Levy writes that Waddell was "a decidedly different sort of child". At the age of three, he wandered over to a local fire station and stayed for several days. Waddell did not attend school very often, but he was considered to be literate. He strengthened his arm as a child by throwing rocks at birds he encountered while plowing the family's land. He also worked on mining and drilling sites as a youngster, which helped his conditioning.

Waddell's career wound through a number of teams. Waddell was unpredictable – early in his career, he would leave mid-game to go fishing. He had a longstanding fascination with fire trucks and had run off the field to chase after them during games. He performed as an alligator wrestler in the offseason. He was easily distracted by opposing fans who held up puppies and shiny objects, which seemed to put him in a trance on the mound. An alcoholic for much of his short adult life, Waddell reportedly spent his entire first signing bonus on a drinking binge (Sporting News called him "the sousepaw"). Waddell's eccentric behavior led to constant battles with his managers and scuffles with bad-tempered teammates.

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