Cubs trade Lou Brock to the Cards for Ernie Broglio (June 15, 1964)
When the Cubs traded away Brock, he was a 24-year-old with a .260 average in two big league seasons. "Brock struck out a lot and didn't know how to run the bases," said Bill White, who played first base for St. Louis in 1964. "We thought we had given up too much." Broglio was a good pitcher, winning 70 games in a little more than five seasons for the Cubs before being traded, and leading the NL in wins with his 21-9 record in 1960, but he had developed a sore arm and went only 7-19 in two-plus seasons with the Cubs. Brock helped the Cards take advantage of the 1964 Phils astounding collapse. St. Louis won the NL flag and beat the Yankees in the World Series. Brock hit .348, stole 33 bases ... and then went on to lead the NL in steals eight times and bat over .300 eight times. He became a Hall-of-Famer in 1985.
"That was the greatest deal made at the deadline," said Jerome Holtzman, MLB's official historian. "It was one of the worst trades in the history of the Cubs."
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</td></tr><tr><td width="195">[FONT=verdana, arial, geneva][/FONT]</td></tr></tbody></table> 2. Red Sox send Jeff Bagwell to Houston for reliever Larry Andersen (Aug. 31, 1990)
Bagwell was a Double-A third baseman in the Red Sox system when Boston sent him packing to the Astros in exchange for Andersen, a 37-year-old who Boston acquired for their stretch run. The Red Sox went on to finish first in the AL East in 1990 before losing the ALCS in four straight to Oakland. Andersen pitched only 22 innings for the Sox, and was only one-for-four in the save department. In 1991 he was off to San Diego. Bagwell's in his 12th season with the Astros; in his first 11 seasons, he had a .969 OPS. He was the 1994 NL MVP and is probably on his way to the Hall of Fame.
Blue Jays send David Cone to Yankees for pitchers Marty Janzsen, Jason Jarvis and Mike Gordon (July 28, 1995)
The Yankees most recent dynasty began in 1995, and Cone was a key ingredient in the Pinstripers 1995 playoff push, going 9-2. During the next five seasons, the aging right-hander was a team leader, was named to the All-Star team twice, led the AL in wins with 20 in 1998, and compiled a 55-38 record. Oh, and he pitched a perfect game. None of the pitchers the Blue Jays acquired played in the majors