For years, Baldwin was an enigma to the Chicago White Sox. A 6′ 3″ right-hander in the classic power-pitcher mode, Baldwin arrived in the big leagues with a knee-buckling curveball and a serviceable fastball that often fell flat at the wrong moments. He showed promise in his rookie season of 1996, going 11-6 with a 4.42 ERA, but infuriated the club with his inconsistency over the next three years. After a disappointing sophomore campaign and an atrocious start to 1998, Baldwin was exiled to the bullpen for six weeks by manager Jerry Manuel. The relief stint helped him regain command of his curveball, and after rejoining the rotation in mid-June he closed the year on an 11-3 run with a 3.45 ERA in 17 starts. After his strong finish Chicago expected him to emerge as the staff ace in 1999, but Baldwin wound up reliving the sins of the previous year. A nagging tendency to leave pitches up in the strike zone produced high home run totals all season long. Before the All-Star break he won just four times against nine defeats, giving up more than six-and-a-half runs per nine innings. Baldwin rewarded Manuel’s patience, however, with another second-half metamorphosis that saw him collect eight wins on the strength of a 3.62 ERA. The 2000 season would mark an odd reversal of fortune, as Baldwin bolted from the starting gate to emerge as one the American League‘s top starters the first two months of the season. His 11 wins in the first half not only earned him his first All-Star selection, but also helped the surprising White Sox open a big lead in the AL Central. But shoulder problems plagued him throughout the second half, limiting his effectiveness and ultimately sidelining from mid-August through late September. Baldwin returned just in time for post-season play, and delivered a valiant performance in Game Three of the Division Series at Seattle. He allowed the Mariners just three hits and one run over six innings, but Chicago lost the game and the series when Seattle scratched out a tie-breaking run in the bottom of the ninth. After the season Baldwin underwent surgery to remove a bone chip and repair fraying in his ailing shoulder. After being offered just a one-year contract in the offseason, Baldwin knew he wasn’t going to be in the White Sox’ long-term plans. When he got off to a poor start in 2001, as Chicago did as a whole, quickly falling behind the Minnesota Twins and Cleveland Indians in the division, trade rumors began to swirl. The big righty entered mid-June mired with a 2-4 record and 4.36 ERA, and though over the next month and a half he went 5-1, Baldwin was traded to the Los Angeles Dodgers in late July for three minor leaguers.