Fansided

Top 25 MLB trades of all time

By Joshua Sadlock

NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images) /
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SAN FRANCISCO – SEPTEMBER 6: Curt Schilling #38 of the Arizona Diamondbacks delivers the pitch during the game against the San Francisco Giants at Pacific Bell Park on September 6, 2003 in San Francisco, California. The Giants defeated the Diamondbacks 5-4 in 11 innings. (Photo by Justin Sullivan/Getty Images)
SAN FRANCISCO – SEPTEMBER 6: Curt Schilling #38 of the Arizona Diamondbacks delivers the pitch during the game against the San Francisco Giants at Pacific Bell Park on September 6, 2003 in San Francisco, California. The Giants defeated the Diamondbacks 5-4 in 11 innings. (Photo by Justin Sullivan/Getty Images) /

12. Curt Schilling to the Diamondbacks, 2000

  • Diamondbacks get: Curt Schilling
  • Philadelphia Phillies get: Omar Daal, Nelson Figueroa, Travis Lee, Vicente Padilla

The Boston Red Sox, Baltimore Orioles and Houston Astros might still be kicking themselves for trading Curt Schilling in the early 1990s (although the Red Sox eventually got him back and came out just fine). Schilling had been traded three times by 1992 when he was traded to the Philadelphia Phillies. Some of the players that Schilling was traded for are now beyond laughable — Mike Boddicker, Glenn Davis, Jason Grimsley, are you kidding me?

The teams that gave up on Schilling had good reason, as he had done little to show he could be a useful, long-term MLB pitcher. The Phillies finally gave Schilling the chance to pitch out of the rotation and he did not disappoint, going 14-11 in 1992 while leading the league in WHIP and hits per nine. Philadelphia came painfully close to winning the 1993 World Series, which they reached on the back of Schilling, the MVP of the NLCS.

By 2000, Schilling was done with playing on lousy teams in Philadelphia and a trade was worked out to send him to the Arizona Diamondbacks. Already considered one of the best strikeout pitchers of his generation, Schilling made himself even better in Arizona. He led the league with 22 wins in 2001 and then went on a tear in the playoffs. The run ended with Schilling sharing World Series MVP honors with Randy Johnson.

Schilling never won a Cy Young, but finished second three times and had three 300-strikeout seasons. He went 4-0 with a 1.13 ERA in seven playoff starts for the Diamondbacks. After going 58-28 in parts of four seasons with Arizona, Schilling signed back with the Red Sox and only added to his postseason legend with another World Series title.

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