Curt Schilling
Curt Schilling was a longtime pitcher who blossomed into a superstar in his 30's, and had two of the best postseason runs ever by a pitcher, which helped vault him into the upper echelon of all-time players.
Schilling first pitched in the majors for Baltimore in 1988, but it took him until 1990 to get his first win, the only one he would record for the Orioles. He pitched out of the bullpen for the Astros after that, but still was not notable in any way.
He joined the Phillies in 1992, and that is where his career started to improve. He had 14 wins and a 2.35 ERA in that first season, then got his first taste of the postseason in 1993, where he started to earn his reputation as a big-game player. He won the NLCS MVP after posting a 1.69 ERA in two starts while striking out 19 Braves, then pitched a shutout while facing elimination in the World Series, but the Phillies ended up losing anyway.
After a couple of down seasons, he bounced back in a big way in 1997, leading the league with 319 strikeouts, the most he would have in his career, and 133 more than he had ever had before, making it the best regular season of his career.
The next season he threw exactly 300 strikeouts while also leading the league with 15 complete games and pitching more innings than any other pitcher. Although he was having great success, his team wasn't, and he requested a trade to a contender, and he got his wish in 2000, when he was sent to the Arizona Diamondbacks.
His first season in the desert was a memorable one, as he led the league with 22 wins, while posting a 2.98 ERA and striking out 293 batters. The Diamondbacks made the playoffs, where Schilling was spectacular, with a 4-0 record, 1.12 ERA, and 56 strikeouts, including 26 strikeouts in 21 innings in the World Series, where he shared the MVP award with Randy Johnson after Arizona upset the 3-time defending champion Yankees.
He was just as great in 2002, with a 23-7 record and 316 strikeouts, which was his third time reaching the 300-strikeout mark. For the second year in a row, he finished as the runner-up in the Cy Young voting to his teammate, Randy Johnson, and he pitched great in the playoffs, striking out 7 in 7 innings and giving up only one run, but Arizona fell to Saint Louis in the NLDS.
After a down year, he was traded to the Red Sox, where he led the league with 21 wins in his first season, and finished as the Cy Young runner-up for the third time in 4 seasons. He pitched through an ankle injury in the playoffs, and became famous for his bloody sock in game 6 of the ALCS, and the Red Sox won their first World Series in decades.
Injuries slowed him over his final 3 seasons, but he again played well in the 2007 playoffs, going 3-0 in 4 starts as the Red Sox won another title. His World Series win made him the second pitcher over 40 in history to start and win a World Series game. After missing the following season with a shoulder injury, he retired before the 2009 season began.
Schilling is one of the best pitchers since the Cy Young award began who did not receive the honor. He finished his career with 3116 strikeouts, #15 all time. While his time as a superstar was relatively short compared to others around him on this list, he had 4 extremely great seasons, and 2 of the best playoff runs in history, which earned him this spot on the list of the all-time greats.
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