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The teams trading Curt Schilling always got worse value in return

Curt Schilling has been in the news for his boisterous opinions, but his change of employment is just another in a long line of transactions in his baseball past.

Curt Schilling, pitching for his fifth MLB team.
Curt Schilling, pitching for his fifth MLB team.
Elsa/Getty Images

Curt Schilling is no stranger to being let go. Long before he became the target of Baseball Twitter’s ire for sharing controversial memes on his Facebook page, Schilling was a Hall of Fame-caliber pitcher. But his career path was unusual in that en route to becoming one of the dominant pitchers of the 1990s and early-2000s, he was traded five times.

One doesn’t need to be a 90s kid to remember the iconic moments of his career – his shutout of the Toronto Blue Jays in Game 5 of the 1993 World Series with his Philadelphia Phillies facing elimination, his World Series co-MVP shared with Randy Johnson in 2001 when the Arizona Diamondbacks and the New York Yankees met in the greatest World Series of the 21st century [Ed's note - bold statement], and the bloody sock in Game 6 of the 2004 ALCS.

But long before those career-defining moments, Schilling was a second-round draft pick in the 1986 January Draft by the Boston Red Sox out of Yavapai College in Prescott, Ariz. Yavapai is a junior college that has produced 21 major leaguers, including Ken Giles, Bob Howry, and Billy Hatcher.

The Red Sox found a good bargain for Schilling, who was the best player taken in the now-defunct draft by rWAR. Schilling amassed 79.9 wins above replacement by the Baseball-Reference formula, while Moises Alou (Round 1, Pick 2, Pirates) at 39.7 and Ray Lankford (Round 3, Pick 10, Cubs) at 38.1 were the next-best players taken.

The Red Sox would have to wait nearly 18 years to finally have Schilling take the mound for them. As the trade deadline grew near in 1988, the Red Sox found themselves in a race for the American League East crown and wanted to bolster their starting rotation for the home stretch, as many teams are wont to do. So they decided to ship the 21-year-old Schilling, who was then with Double-A New Britain, and rookie outfielder Brady Anderson to the Baltimore Orioles for Mike Boddicker.

The 30-year-old Boddicker was great down the stretch in 1988 for Boston, as the former All-Star posted a 2.93 FIP (76 FIP-) and racked up 2.5 rWAR in 89.0 frames. He spent two more years with the Red Sox, falling back to a league-average 3.71 FIP in 1989 and improving to 3.51 in 1990, tossing 211.2 and 228.0 innings, respectively.

His two-and-a-half seasons with the Red Sox netted him 11.6 rWAR in 528.2 innings, yet the trade still goes down as a loss for Boston because of what they gave up. Anderson spent 14 seasons with Baltimore and became one of the faces of the dominant mid-90s Orioles squads. He was worth 34.7 rWAR with the O’s and infamously hit 50 home runs out of nowhere in 1996.

Schilling was in the majors by the end of 1988 – getting the call directly from Double-A Charlotte – and pitched poorly in four starts with the Orioles, as you might expect from a pitcher who skipped Triple-A.

In 1989 Schilling spent the year with Triple-A Rochester, where he pitched well, but another cup of coffee with the Orioles did not go so well. The 1990 season saw Schilling split time more equitably between Rochester and Baltimore, where he finally began to see some success.

After posting a 2.94 FIP and three saves in 46.0 innings out of the bullpen for the Orioles in 1990, Schilling was dealt by the Orioles along with Pete Harnisch and Steve Finley to the Houston Astros for Glenn Davis.

Davis had three poor, injury-riddled years in Baltimore before being out of baseball, hitting .247/.312/.400 with the Orioles.

Harnisch spent four seasons as a member of the Astros and had two good years and two not-so-good years. He made his lone All-Star team in 1991, posting career-bests in ERA (2.70), RA/9 (2.95), and rWAR (4.6). Harnisch regressed in 1992 but came back strong in 1993 to lead the National League with four shutouts and posted a 2.98 ERA and 3.4 wins above replacement.

He struggled again in the strike-shortened 1994 season, getting hit hard to the tune of a 5.40 ERA and 4.93 FIP. After the season, the Astros traded Harnisch to the New York Mets for two players to be named later (Andy Beckerman and Juan Castillo).

Finley lasted four seasons with Houston as well and enjoyed four productive seasons. These were the days before Finley was a power hitter – known more for his speed and defense in center field more than anything else. In his four years with Houston, Finley legged out 41 triples, stole 110 bases, and was worth 16.0 rWAR. It was arguably the best four-year stretch of his 19-year career.

Then there was Schilling, who spent just one season with Houston. Schilling again split time between Triple-A and the majors in 1991, starting the season as Houston’s closer and finishing the year with eight saves. He pitched to a 2.87 FIP but just a 3.81 ERA.

Schilling’s problem early in his career was his lack of control. In his first four seasons he combined to walk 4.4 batters per nine innings, and he hadn’t quite found his strikeout stuff yet, fanning just 7.0 per nine.

With the 1992 season on the horizon, the Astros dealt Schilling to the Philadelphia Phillies for Jason Grimsley. Grimsley spent the entire 1992 season as a starter for the Triple-A Tuscon Toros and never played with the Astros. He was released by Houston just prior to the 1993 season.

Meanwhile, the now 25-year-old Schilling came into his own as a member of the Phillies, pitching well enough out of the bullpen to insert himself into the starting rotation on May 19, 1992 against Houston of all teams. He made 26 starts that year and threw 10 complete games including four shutouts, and his 0.990 WHIP led the NL. Schilling wouldn’t pitch from the bullpen again until September 2002.

Schilling spent nine years with the Phillies, accumulating 36.7 rWAR, and recorded a 3.27 FIP and improved his K:BB ratio to 3.74 (8.4 K/9 and 2.3 BB/9). He made three straight All-Star teams from 1997-1999 and earned Cy Young and MVP votes in 1997 after striking out 319 batters in 254.1 innings and posting a 2.62 FIP.

The marriage between Schilling and the Phillies came to an end on July 26, 2000 when the Phillies – out of contention as the Mets and Braves battled for NL East supremacy – dealt Schilling to the Arizona Diamondbacks, who were battling with the San Francisco Giants in the NL West. The Diamondbacks gave the Phillies Omar Daal, Nelson Figueroa, Travis Lee, and Vicente Padilla.

Once again, the team trading Schilling would get the short end of the stick. Daal made 44 starts in a year and a half with the Phillies with mediocre results before being dealt to the Los Angeles Dodgers for Jesus Cordero and Eric Junge.

Figueroa made 19 appearances and was league-average for the Phillies in 2001. Then he was claimed off waivers by the Milwaukee Brewers at the end of the season. He was out of baseball from 2005-2007, then enjoyed a career renaissance with the Mets, Phillies, and Astros from 2008-2011.

Lee hit .258/.343/.402 across three seasons with the Phillies, racking up just 2.3 rWAR before signing as a free agent with the Tampa Bay Devil Rays before the 2003 season.

Padilla enjoyed the most success with the Phillies. He lasted six seasons, was an All-Star in 2002, and had his own version of the Wolf Pack, Padilla’s Flotilla. Padilla was worth 5.3 rWAR with the Phillies, but all of that value came from his 2002 and 2003 seasons, when he made 64 starts with a 3.99 FIP.

In Arizona, Schilling elevated himself from very good pitcher to truly elite status. Paired atop the rotation with Randy Johnson, Schilling sustained a 10.1 K/9 and 1.3 BB/9 for 781.2 innings, finishing second to the Big Unit in the NL Cy Young Award voting twice. Limited to just 24 starts in 2003 because of appendix surgery and a broken right hand, the Diamondbacks became the fifth team to trade Schilling – this time to the Red Sox where it all began.

Arizona’s haul for Schilling was Mike Goss, Casey Fossum, Brandon Lyon, and Jorge De La Rosa. Goss never advanced past Double-A but had a stellar eight-year career in various independent leagues.

Fossum made 26 starts in 2004 with the Diamondbacks before being traded to Tampa Bay before the 2005 season for Jose Cruz. With Arizona, Fossum had a 5.78 FIP and was worth an atrocious -1.4 rWAR.

Lyon had an up and down career, sometimes serving as a closer. He had a 4.03 FIP in four years with the Diamondbacks, but they were progressively: 5.78, 4.08, 3.44, and 3.84. He saved 42 games in the four years and had 2.1 rWAR in 73 games in 2007.

De La Rosa was a Diamondback for three days before being shipped to the Milwaukee Brewers along with five other players in the Richie Sexson trade.

Schilling finished out his career with the Red Sox, winning two more World Series and wearing one of the most famous socks in baseball history. Now in his late-30s and with a bad ankle, Schilling was not the dominant force in Boston that he was in Arizona, but he still managed 17.8 rWAR in four years and a 5.31 K:BB ratio and 3.57 FIP.

The team acquiring Schilling in all of these trades never really had much to regret in terms of the value they received. They always got more production coming to them than they gave up, and he was a major player in three championship teams. The teams acquiring Schilling gained a combined 149.6 wins above replacement, while the teams dealing him got just 20.4 rWAR in return.

Schilling has had a turbulent post-playing career – from his 38 Studios fiasco and his battle with cancer to his recent dismissal from ESPN for repeatedly sharing politically-charged memes on his Facebook page and then digging his heels in when backlash occurred. ESPN likely won’t regret their recent Schilling-ectomy, but it would be the first time that he won’t be missed.

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Joe Vasile is a contributor at Beyond the Box Score and is the Broadcasting and Media Relations Assistant for the Salem Red Sox, the Class-A Advanced affiliate of the Boston Red Sox. He does not know when Andrew Benintendi and Yoan Moncada are getting promoted to Double-A, so stop asking. Follow him on Twitter at @JoeVasilePBP.