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All-Time Red Sox Roster: Curt Schilling

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This member of the All-Time team has undoubted Hall of Fame credentials, but has been mired in controversy since leaving baseball.

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2007 World Series GM 2 - Colorado Rockies v Boston Red Sox

Seasons in Boston: 2004-2007

Honors: 6x All-Star, 3x World Series Champion, 2001 World Series MVP

Red Sox Numbers: 3.95 ERA, 1.21 WHIP, 53 W, 9 SV, 574 K, 85 ERA-, 15.1 fWAR

Signature Season (2004): 226.2 IP, 203 K, 21 W, 3.26 ERA, 1.06 WHIP, 6.5 fWAR


Any discussion involving Curt Schilling is complicated because it’s become impossible to be just about baseball. From a purely baseball perspective, however, there is nothing complicated about Schilling. To put it simply, he’s vastly underrated and I believe he is a top 20 starter in baseball history. FanGraphs WAR certainly supports me as he is ranked exactly 20th by that metric. Schilling is one of just 18 pitchers in league history to strike out over 3000 batters, and of those 18 players only Schilling, Roger Clemens, and the still-active Justin Verlander are not in the Hall of Fame. Furthermore, only Nolan Ryan (six times) and Randy Johnson (six times) have struck out 300 batters in a season (Modern Era) more times than Schilling, who did it three times. With over 200 wins and countless postseason accolades, Schilling’s resume speaks for itself. The elephant in the room is what Schilling has said off the field that has detracted from his greatness on the field. As Joe Posnaski put it in his recent Top 100 article on him, “With Schilling, teammates loved him on the day he pitched, hated him the other four days.”

Schilling makes my roster as a reliever rather than a starter because sometimes you need to fudge things a little to include great players. Over the course of his career Schilling did throw 181.2 IP in relief while racking up 22 saves. Nine of those saves came with the Red Sox in 2005 after offseason surgery pushed him to a bullpen role. Not having him on this team would feel wrong because of just how much he meant to both the 2004 and 2007 World Series runs. During those two runs he won at least one game in each round of the postseason and never lost in elimination games or clinchers. Throughout his career a hallmark of Schilling’s greatness was his ability to miss bats while not walking anyone, and he, in fact, ranks number one in baseball history among pitchers with at least 2000 innings with a 4.66 strikeout to walk ratio. Over his career, he had 64 starts with seven or more strikeouts and zero walks, the most in baseball history. This ability to miss bats and not hurt himself with walks makes him an ideal conversion to relief for the purposes of this exercise.

In January of 1986 Schilling was drafted by the Red Sox in the second round and began his baseball career in the same organization with which he would ultimately end it. In 1988, Schilling and teammate Brady Anderson were traded to the Orioles for pitcher Mike Boddicker. He then bounced around from the Orioles to the Astros and then finally to the Phillies where he broke in as a starter in 1992. That year, at 25 years old, Schilling threw 226 ⅓ innings while posting an ERA of 2.35 and led baseball in WHIP at 0.99. Even with all that, he didn’t make the All-Star team or receive a single Cy Young vote. In fact, despite having many other very strong seasons with the Phillies, Schilling wouldn’t make his first All-Star team until 1997 at the age of 30. That began a streak of three All-Star bids in a row. In 1998, he had another excellent season striking out 300 batters for the second year in a row and throwing 15 complete games, yet he again didn’t receive any Cy Young votes.

In 2000, Schilling was traded to the Diamondbacks where he enjoyed the best years of his professional career. He was legendary in both the 2001 and 2002 seasons, yet finished second to his teammate Johnson in the Cy Young voting both years. In the 2001 postseason he set the record for most strikeouts in a single postseason with 56 and he threw 48 ⅓ innings with a 1.12 ERA and a 0.64 WHIP, with three complete games to boot. Schilling had some bad luck with his excellent seasons as they tended to match up with those from other All-Time greats. The four times he received Cy Young votes he lost to Pedro Martinez (1997), Johnson (2001 and 2002), and Johan Santana (2004).

Theo Epstein watched Schilling dismantle the Yankees lineup during the 2001 World Series and following the 2003 Aaron Boone debacle he set his sights on acquiring this Yankee slayer. After a Thanksgiving feast at the Schilling home a deal was made to send him to the Red Sox in exchange for Casey Fossum, Jorge de la Rosa, Brandon Lyon, and Michael Goss. Schilling enjoyed immediate success during the regular season as a member of the Red Sox, winning a league-best 21 games while posting a league-leading strikeout to walk rate for the fifth time in six years. In the postseason, Epstein really got what he was looking for. Schilling won Game One of the ALDS vs the Angels, Game Six facing elimination at Yankee Stadium, and Game Two of the World Series at home vs the Cardinals. Game Six was, of course, the famous bloody sock game where he was pitching on tendons sutured in place by Dr. Bill Morgan.

Schilling replicated this feat in 2007 by winning games in each round of the postseason including the ALDS clincher and the key Game Six of the ALCS vs the Indians while facing elimination and in the World Series vs Colorado. By the time his career was over Schilling compiled a nearly unrivaled postseason record and a deserved reputation as one of best big game pitchers in baseball history. Schilling’s postseason record is 11-2 with a 2.23 ERA, 0.97 WHIP, and 50 ERA- over 133 ⅓ innings. He has the best winning percentage of all time for any starter with more than 10 decisions at .846 and the best win probability added of all-time among starting pitchers at 4.1. His 2001 postseason run is the single best WPA of all-time at 2.1. He has a career postseason ERA of 1.37 in five games facing elimination and of 1.16 in three games with the opportunity to clinch the series.

Following his storied career Schilling has gotten himself in hot water a few times with political comments, bigoted rhetoric, and financial decisions. His 38 Studios video game venture cost him much of his baseball fortune and led to legal battles with the state of Rhode Island. He also has said several extremely controversial things online with the most famous being his “Ok, so much awesome here…” Tweet about a T-Shirt promoting the hanging of journalists. This has undoubtedly hurt his Hall of Fame chances, but in recent years his prospects have improved. Earlier this year he received 278 votes accounting appearing on 70% of voter ballots. He sits 20 votes shy of the Hall of Fame threshold with two years left on the ballot.

It wouldn’t be fair to look at his negative contributions to society without looking at the positive. Schilling won many awards for his charity work and personal attributes over the course of his career including the Hutch Award, the Roberto Clemente Award, the Charlie Hough Good Guy Award, the Branch Rickey Award, the Lou Gehrig Award, and the USA Today’s Most Caring Athlete Award. These awards represent the good side of Schilling off the field and ironically the Good Guy award is given out by the BBWAA, with whom Schilling now finds himself embattled with. His work with ALS and skin cancer have been extensive over the course of Schilling’s long time in the public eye. People are complicated and Schilling is as well, but one thing is certain: his pitching was transcendent and he belongs on this team.


Introduction and Honorable Mentions Part One

Honorable Mentions Part Two

Bench: Bobby Doerr

Bench: Jason Varitek

Bench: Manny Ramirez

Bench: Tris Speaker

Bench: Carl Yastrzemski

Starting Catcher: Carlton Fisk

Starting First Baseman: Jimmie Foxx

Starting Second Baseman: Dustin Pedroia

Starting Third Baseman: Wade Boggs

Starting Shortstop: Nomar Garciaparra

Starting Left Fielder: Ted Williams

Starting Center Fielder: Fred Lynn

Starting Right Field: Mookie Betts

Starting Designated Hitter: David Ortiz

Reliever: Dick Radatz