This Day in Transaction History: Astros deal Curt Schilling to Phillies

Curt Schilling
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As a recurring column idea, Bill will expound upon one interesting transaction that occurred on a particular day in baseball history. It won’t always be the most exciting or most impactful transaction, but always something interesting. Feel free to share which transactions stand out to you in the comments.

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On this day on 1992, the Phillies pulled off what would become one of the most lopsided trades in baseball history. They swapped young pitchers with the Astros, sending 25-year-old Jason Grimsley to Houston in exchange for 25-year-old Curt Schilling. Neither pitcher had an amazing résumé to that point: Grimsley posted a 5-12 record with a 4.35 ERA, 90 strikeouts, and a whopping total of 103 walks over 136 2/3 innings. Over parts of four seasons with the Orioles and Astros, Schilling went 4-11 with a 4.16 ERA, 113 strikeouts, and 71 walks over 145 innings.

Grimsley did not last long in the Astros organization. He spent the 1992 season with Triple-A Tucson, posting a 5.05 ERA across 20 starts and six relief appearances. The Astros released him after the season. It took a while, but Grimsley ultimately found a role as a journeyman reliever, enjoying a 15-year career. He retired with a 4.77 ERA. Grimsley was more well known for getting caught up in baseball’s drug scandal in the early and mid-2000’s.

Schilling, meanwhile, went on to become the face of the Phillies. He had a spectacular 1992 campaign, registering 226 1/3 innings with a microscopic 2.35 ERA. Though his regular season performance was markedly worse in 1993, finishing with a 4.02 ERA, he did help the Phillies break their decade-long postseason drought. In the playoffs for the first time, Schilling made a name for himself, as three of his four October starts were outstanding, including a crucial shutout of the Blue Jays in Game 5 of the World Series.

Schilling truly came into his own in 1996, the first full season after a work stoppage. In four seasons from 1996-99, Schilling was a three-time All-Star, compiling an aggregate 3.22 ERA and a 953/213 K/BB ratio over 886 2/3 innings spanning 120 starts. He finished fourth in NL Cy Young balloting in ’97 behind Pedro Martínez, Greg Maddux, and Denny Neagle. Unfortunately for him, the Phillies were otherwise quite terrible, winning 287 of 648 games (.443). The 2000 season was another lost year and things became tense between Schilling and the Phillies. He requested a trade to a contender and the team granted him his wish, dealing him to the Diamondbacks ahead of the non-waiver trade deadline for pitchers Vicente Padilla, Nelson Figueroa, and Omar Daal, as well as first baseman Travis Lee.

It is harrowing to think of how bad the Phillies would have been without Schilling all those years, 1993 notwithstanding. Despite the lack of team success, Schilling himself certainly benefited as the de facto ace of the rotation and becoming a vocal team leader. That being said, the trade out of Philadelphia did wonders for Schilling’s career.

In 2001, the Diamondbacks won the NL West on the back of a front-loaded starting rotation that featured Randy Johnson and Curt Schilling. Schilling, in what would become a theme, finished second in Cy Young balloting to Johnson. He led baseball in innings (256 2/3) and wins (22) while leading the NL in complete games (six). He added a 2.98 ERA with 293 strikeouts. The duo carried the D-Backs through the postseason as well. Schilling made six starts, going the distance in his first three including a NLDS Game 1 shutout of the Cardinals. Overall, Schilling went 5-1, allowing just six runs on 25 hits and six walks with 56 strikeouts over 48 1/3 innings that postseason. Most importantly, he pitched the game of his life in Game 7 of the World Series against the Yankees, yielding a pair of runs over 7 1/3 innings. The game, of course, was memorably won on a Luis Gonzalez walk-off single up the middle against Mariano Rivera.

Depending on which stats you like to use, Schilling’s 2002 season was arguably better than ’01. He again finished second to Johnson in NL Cy Young voting, going 23-7 with a 3.23 ERA over 259 1/3 innings. Schilling also joined the 300-strikeout club for the third time in his career with 316 punch-outs. To date, Schilling is one of only six pitchers with at least three 300-strikeout seasons.

Schilling’s time in Arizona was short. After the 2003 season, the D-Backs traded him to the Red Sox in another deal that proved fortuitous for his career. During the 2004 postseason, Schilling dealt with an ankle injury. Nevertheless, he took the mound for his start in Game 6 of the ALCS against the rival Yankees. His effort apparently ruptured sutures in his ankle, soaking his sock in blood. That start was henceforth referred to as the “bloody sock game.” Schilling pitched seven strong innings, holding the Yankees to a lone run in a Game the Red Sox won 4-2. The Red Sox went on to win Game 7, winning the series despite losing the first three games, a first in baseball history. Schilling started Game 2 of the World Series, allowing just one unearned run over six frames as the Red Sox went on to sweep the Cardinals to win their first championship in 86 years, ending the storied “Curse of the Bambino.”

With just a little bit of gas left in the tank, Schilling won one more championship for good measure with the Red Sox in 2007 at the age of 40. Outside of an ugly start against the Indians in Game 2 of the ALCS, Schilling was solid. He blanked the Angels over seven innings in Game 3 of the ALDS, held the Indians to two runs over seven innings in Game 6 of the ALCS, and limited the Rockies to one run over 5 1/3 innings in Game 2 of the World Series.

For a whole host of reasons unrelated to his baseball prowess, Schilling came up just shy of earning the 75 percent of the BBWAA vote needed to earn induction into the Hall of Fame. We have talked about that at length here, so I won’t rehash that in this column. He has two more years of eligibility remaining. In the event he does ultimately earn enshrinement in Cooperstown, New York, an interesting question will be raised: which team’s cap will he wear on his Hall of Fame plaque? Is it the Phillies, the team he was with the longest during his 20-year career and with which he spent his formative years? Is it the D-Backs, where he had back-to-back runner-up Cy Young finishes while winning his first championship? Or is it the Red Sox, where he won two championships in four years?

At the time, Schilling’s post-Philadelphia success stung for the Phillies, who couldn’t seem to do much of anything right. After Schilling’s dominant performance in the 1993 playoffs, the Phillies wouldn’t reach the postseason again until 2007. At least the Phillies can claim ownership of one of the most lopsided trades in baseball history. The Phillies, in fact, have done that multiple times through the years, as the Steve Carlton and Bobby Abreu trades are also widely regarded as one-sided.