At first because of his immature behavior, and later because of his alcoholism, Waddell's career wound through a number of teams. His first pro contract was with Louisville (for $500), pitching two league games and a couple of exhibitions with the team at the end of the 1897 season. When the season ended, he was loaned to the Detroit Wolverines of the Western League to gain professional seasoning.
After defaulting on rent and being fined by owner George von der Beck, Waddell left Detroit in late May to pitch in Canada before eventually returning to Homestead, Pennsylvania to pitch semi-pro baseball there. Pittsburgh retained his rights, however, and he was loaned to Columbus of the Western League in 1899, continued with the team when the franchise moved mid-season to Grand Rapids, and finished with a record of 26–8. He rejoined Louisville in the final month of the 1899 season and won seven of nine decisions. When the National League contracted to eight teams for the 1900 season, Louisville ownership bought the Pittsburgh franchise and the Louisville franchise was terminated. Louisville's top players, including Waddell, Honus Wagner, Fred Clarke and others, were transferred to Pittsburgh.
Waddell debuted with the Pittsburgh Pirates in 1900, leading the National League in ERA, but his erratic behavior led manager Fred Clarke to suspend him. After pitching semi-pro ball in small towns such as Punxsutawney, Connie Mack learned of Waddell's availability, and with Pittsburgh's approval convinced Waddell to pitch for Milwaukee for several weeks in the summer of 1900. Milwaukee was in the newly-named American League (formerly the Western League), which was not yet directly competing with the National League. When Waddell displayed his prowess for Milwaukee, Pittsburgh management asked for Rube's return. By 1901, however, he had worn out his welcome and his contract was sold to the Cubs, then managed by Tom Loftus, who had had success with Waddell in Columbus/Grand Rapids; but Loftus did not have the latitude to cope with Rube he had had Columbus owner/manager. When problems led to his suspension, Waddell began pitching for semi-pro teams in northern Illinois, as well as Racine and Kenosha, Wisconsin.
Frank Chance and Joe Cantillon then invited Waddell to join a barnstorming team that travelled to California, where he was convinced to stay and joined the Los Angeles Loo Loos in a league that a year later would become the Pacific Coast League. Connie Mack, now in Philadelphia, was desperate for pitching, and when he learned Rube was pitching in California, he dispatched two Pinkerton agents to sneak Waddell back to Philadelphia, where he would lead the Philadelphia Athletics to the 1902 American League crown. Much later, Mack described his star left-hander as, "...the atom bomb of baseball long before the atom bomb was discovered."
Waddell's pitching repertoire usually consisted of only two pitches: one of the fastest fastballs in the league and a hard curve. But he had command of many more pitches, including slow curves, screwballs, "fadeaways" and even a "flutterball". Mack once said that Waddell's curve was, "even better than his speed... had the fastest and deepest curve I've ever seen."
Waddell enjoyed waving his teammates off the field and then striking out the side. He actually did so only in exhibition games, since the rules prohibit playing with fewer than nine men on the field in regulation play. But in a league game in Detroit, Waddell actually had his outfielders come in close and sit down on the grass to watch him strike out the side. Once the stunt almost backfired. Pitching an exhibition game in Memphis, he took the field alone with his catcher, Doc Powers, for the last three innings. With two out in the ninth, Powers dropped the third strike, allowing the batter to reach first. The next two hitters blooped pop flies that fell just behind the mound. Waddell ran himself ragged, but finally fanned the last man.
His career stats were 193–143, 2,316 strikeouts, and a 2.16 earned run average, with 50 shutouts and 261 complete games in 2961 innings pitched.
In his prime, Waddell was the game's premier power pitcher, with 302 strikeouts in 1903, 115 more than runner-up (Bill Donovan), and followed that up with 349 strikeouts in 1904, 110 more than the runner-up (Jack Chesbro). No other pitcher would compile consecutive 300-strikeout seasons until Sandy Koufax in 1965 and 1966.
Waddell's 349 strikeouts was the modern-era season record for more than 60 years, and remains sixth on the modern list. (In 1946, it was initially believed that Bob Feller's 348 strikeouts had broken Rube's single-season mark, but research into his 1904 season box scores revealed uncounted strikeouts that lifted him back above Feller.) He still holds the American League single season strikeout record by a left-handed pitcher.
In time, however, his drinking, exacerbated by an horrific marriage to May Wynne Skinner (his second of three wives), and a series of injuries in 1905 and 1906, began to erode his relationships with his Athletic teammates. One-time friend catcher Ossee Schreckengost, who regularly fetched alcohol and fishing poles for Rube, squabbled with both Waddell and Mack for being treated differently for the same offenses. Other players complained about Rube's lack of dependable behavior, and following the 1907 season he had ended as the goat of a series that cost the A's the pennant won by the Detroit Tigers, Mack finally lost patience with him and sold Waddell to the St. Louis Browns for $5,000.
Waddell enjoyed one successful season, helping the Browns compete in one of the greatest AL pennant races ever. To make sure he stayed out of trouble during the offseason, Browns owner Robert Hedges hired him as a hunter over the winters of 1908 and 1909. However, further drinking and marital problems with his third wife, Madge Maguire, led to his release in 1910. He finished the season pitching with "Iron Man" Joe McGinnity for Newark in the Eastern League, and never played another major league game.
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