Worst trades in MLB history

Toronto Blue Jays acquire Date Pittsburgh Pirates acquire
Jose Bautista
August 21, 2008
Player to be named later (Robinzon Diaz)
Texas Rangers acquire Date Cincinnati Reds acquire
Josh Hamilton
December 21, 2007
Daniel Ray Herrera
Edinson Volquez
Chicago Cubs acquire Date Cincinnati Reds acquire
cash
December 7, 2006
Josh Hamilton
Miami Marlins acquire Date Minnesota Twins acquire
Jared Camp
December 13, 1999
cash
Johan Santana
Montreal Expos acquire Date Boston Red Sox acquire
Carl Pavano
Player to be named later (Tony Armas Jr.)
November 18, 1997
Pedro Martinez
Seattle Mariners acquire Date Boston Red Sox acquire
Heathcliff Slocumb
July 31, 1997
Derek Lowe
Jason Varitek
Los Angeles Dodgers acquire Date Montreal Expos acquire
Delino Sr. DeShields
November 19, 1993
Pedro Martinez
Houston Astros acquire Date Boston Red Sox acquire
Jeff Bagwell
August 31, 1990
Larry Andersen
Montreal Expos acquire Date Pittsburgh Pirates acquire
Scott Ruskin
Willie Greene
Player to be named later (Moises Alou)
August 8, 1990
Zane Smith
Montreal Expos acquire Date Seattle Mariners acquire
Mark Langston
Player to be named later (Mike Campbell)
May 25, 1989
Brian Holman
Gene Harris
Randy D. Johnson
Oakland Athletics acquire Date Chicago Cubs acquire
Dan Roan
Dennis Eckersley
April 3, 1987
Brian Guinn
David Wilder
Mark Leonette
Montreal Expos acquire Date Baltimore Orioles acquire
Dennis Martinez
Player to be named later (John Stefero)
June 16, 1986
Player to be named later (Rene Gonzales)
Los Angeles Dodgers acquire Date Texas Rangers acquire
Burt Hooton
Dave Stewart
Mark Bradley
Orel Hershiser
December 10, 1982
Jim Sundberg
Toronto Blue Jays acquire Date New York Yankees acquire
cash
Dave Collins
Fred McGriff
Mike Morgan
December 9, 1982
Dale Murray
Tom Dodd
St-Louis Cardinals acquire Date New York Yankees acquire
Willie McGee
October 21, 1981
Bob Sykes
St-Louis Cardinals acquire Date San Diego Padres acquire
Ozzie Smith
Steve Mura
Player to be named later (Al Olmsted)
February 10, 1981
Gary Templeton
Sixto Lezcano
Player to be named later (Luis Deleon)
Milwaukee Brewers acquire Date St-Louis Cardinals acquire
Pete Vuckovich
Rollie Fingers
Ted Simmons
December 12, 1980
Dave LaPoint
David Green
Lary Sorensen
Sixto Lezcano
Milwaukee Brewers acquire Date Boston Red Sox acquire
Cecil Cooper
December 6, 1976
Bernie Carbo
George Scott
St-Louis Cardinals acquire Date Philadelphia Phillies acquire
Rick Wise
February 25, 1972
Steve Carlton
Houston Astros acquire Date Cincinnati Reds acquire
Jimmy Stewart
Lee May
Tommy Helms
November 29, 1971
Cesar Geronimo
Denis Menke
Ed Armbrister
Jack Billingham
Joe L. Morgan