(Editor’s Note: Some previous content was used when compiling this post.)
Since officially moving to Los Angeles in 1958, many player trades occurred that were instrumental in winning 11 National League pennants and five World Series championships. However, along with the deals that were beneficial came the deals that were dreadful. Consequently, people often wonder what may have transpired if a number of these trades could have been undone.
A little over eight years ago, I put together a list of over 50 trades that were seemingly detrimental to the club since relocating to the West Coast. Amidst that group were several deals orchestrated by former general manager Ned Colletti. At the time, a handful appeared to be somewhat haphazard, most notably the Carlos Santana for Casey Blake swap in 2008; but for the most part, flanked by his scouting gurus Logan White and De Jon Watson, many of the trades proved to be mostly unharmful in the end. In the same breath, Andrew Friedman and his troops have yet to be criticized much, although initially, the deal which sent Dee Gordon to the Marlins was embraced with a huge amount of scrutiny.
This year we thought it would be interesting to narrow down the timeline even further, looking at five of the more disastrous deals in recent history. For the sake of having a relatively concrete timeline, we’ve marked the date of the 1988 World Series title as the starting point and began our contemplating from there.
Although some of the transactions listed may seem more prominent than others, the logic used in the rankings is based on the players’ ability at that time and into the future, weighted against what the Dodgers actually received in return.
If any other deals come to mind that you think may have been overlooked, feel free to drop us a line on Twitter or in the comment section below. We hope you enjoy the ride.
No. 5—Gary Sheffield Traded to Atlanta Braves (January 25, 2002)
In a four-player deal that saw pitcher Odalis Perez, outfielder Brian Jordan and reliever Andrew Brown sent to the Dodgers from the Braves, Los Angeles sacrificed their most formidable power threat at the time, Gary Sheffield.
After leaving the Dodgers, Sheffield continued to produce. He hammered 25+ home runs five more times after the trade, scored 100+ four times, and drove in 120+ runs three times. He was also selected to three All-Star teams after his tenure with the Dodgers.
Perez started strongly with Los Angeles before fading and eventually being traded to the Kansas City Royals before the trade deadline in 2006. Brown roamed the Dodgers’ farm system before finally making his MLB debut with the Cleveland Indians four years later.
Jordan never lived up to his expectations in Los Angeles, and was granted free agency after the 2003 season.
No. 4—Dave Roberts Dealt to Red Sox for Henri Stanley (July 31, 2004)
Roberts had been a staple atop of the Dodgers batting order for three seasons, and upon settling in Boston, contributed mightily during the Red Sox playoff run that same season, most notably the infamous stolen base in Game 4 of the 2004 ALCS.
In 2006, Roberts went on to produce his signature campaign with the San Diego Padres. During that season, he hit .293/.360/.393 with 13 triples, 49 stolen bases, and 44 RBI in 129 games. And we all know how much of an outstanding manager he turned out to be.
Stanley never made it out of the minor leagues.
No. 3—Mike Piazza sent to the Florida Marlins (May 15, 1998)
In the summer of 1998, the Dodgers were very instrumental in helping the Marlins virtually disseminate their entire organization.
On May 15, Los Angeles sent their franchise player, Mike Piazza, along with third baseman Todd Zeile to the (then) Florida Marlins in exchange for Sheffield, Bobby Bonilla, Jim Eisenreich, Charles Johnson, and Manuel Barrios.
In six seasons with the Dodgers, Piazza was selected to six All-Star squads, was named as the MVP of the 1996 All-Star Game, earned six Silver Slugger Awards, and won the NL Rookie of the Year Award in 1993.
Piazza’s signature season with the Dodgers came in 1997 when he hit an insane .362/.431/.638 with 40 home runs, 32 doubles, 104 runs scored and 124 RBI.
He was enshrined in Cooperstown in July of 2016 wearing the hat of the Mets.
Besides the glove of Johnson behind the dish, the only other positive for the Dodgers was acquiring Sheffield. Sheffield’s benchmark year in Los Angeles arrived in 2000 when he hit .325 with 105 runs scored, 24 doubles, 43 home runs, and 109 RBI, while posting an impressive slugging percentage of .643.
No. 2—Paul Konerko traded for Jeff Shaw (July 4, 1998)
In order to fill an urgent vacancy in the Dodgers’ bullpen, Tommy Lasorda, during his short stint as Dodgers’ GM, dealt first baseman Paul Konerko and pitcher Dennys Reyes to the Cincinnati Reds in July of 1998 in exchange for closer Jeff Shaw.
Konerko was only halfway through his rookie season when he was traded. The Dodgers had absolutely no idea of the first baseman’s potential at that point in time.
Konerko was later named as an All-Star on four occasions, and his benchmark season came in 2006 with the Chicago White Sox when he hit .313 with 97 runs scored, 30 doubles, 35 home runs and 113 RBI. Konerko would go on to play 18 big league seasons, recording 2340 career hits, 439 home runs, 1162 runs scored and 1412 RBI.
Reyes was an effective middle-man for nine different clubs over the course of his 14-year MLB career.
Shaw became the primary closer for Los Angeles over four seasons and retired after his 2004 campaign.
No. 1—Pedro Martinez Dealt to the Montreal Expos (November 17, 1993)
Finally, former Dodgers GM Fred Claire gets credited with making the worst trade in the history of the franchise.
Martinez was only 21 years of age when he left Los Angeles. He eventually developed into one of the most successful power-pitchers that the game has ever seen.
Among his most notable achievements are his three AL Cy Young Awards and his eight All-Star appearances, as well as his Triple Crown Award in 1999. He led the American League in ERA four times, led the AL in strikeouts three times, and led the AL in wins with 23 in 1999. He is a member of the Hall of Fame class of 2015.
DeShields’ career as a Dodger lasted four seasons and was mediocre at best. During that span, his numbers per season averaged out to a .255 batting average with 115 hits, four home runs, and 35 RBI.
DeShields left Los Angeles after being granted free agency in 1996 and eventually retired in 2001.