Baseball’s Most Lopsided Deadline Deals

By Dave Martin
Dave Martin
Dave Martin
Dave Martin is a New-York based writer as well as editor. He is the sports editor for the Epoch Times and is a consultant to private writers.
August 1, 2013 Updated: August 1, 2013

Every year at baseball’s trade deadline (July 31) a number of teams in contention (or teams that think they’re in contention) take a risk on improving their present standings by mortgaging an uncertain future. Teams looking to win it all take calculated risks on short-term rental-players for a prospect or a collection of prospects and hope it works out—both for now and in the future.

It’s a dicey situation due to a number of factors including the well-known fact that baseball prospects are the toughest to project. That’s part of the reason why baseball’s draft is 50 rounds long and teams are excited just to have their first round picks make it to the big leagues—let alone be All-Stars.

Naturally this risky, yet accepted, trading method has yielded a number of uneven deals. Here are the five most lopsided deadline trades since 1990:

Honorable mention: August 25, 2012—Boston trades Adrian Gonzalez, Josh Beckett, Carl Crawford, Nick Punto, and cash to the Los Angeles Dodgers for James Loney and prospects Rubby De La Rosa, Jerry Sands, Ivan De Jesus, and Allen Webster.

Though this trade hasn’t given all these prospects the time to declare a winner in the deal, the sheer volume of undesirable contracts the Dodgers took on does. Between Crawford, Beckett, and Gonzalez, Los Angeles assumed some $200 million worth of liabilities that netted them an 86-76 season last year—two games out of the wild card.

This year Beckett has a 5.19 ERA, Crawford is hitting a decent (though not for his salary) .284 and Gonzalez, the clear desired star of the deal for Los Angeles, has 15 home runs, 65 RBIs, and a .299 average. Had the Dodgers not found Yasiel Puig, who has saved this season, this deal would look even worse.

Boston, which suffered through an awful 69-93 season in 2012 was essentially able to hit the reset button and retool with plenty of cash in hand. Currently they are 64-44 and just a half-game out of first place.

5. July 30, 2004—Tampa Bay trades Victor Zambrano and Bartolome Fortunato to the New York Mets for top prospect Scott Kazmir.

Hard to envision what the Mets (just 49-53 at the time) were thinking with this one. Zambrano, then 28, was a mediocre 35-27 with a 4.47 ERA in four seasons as a starter for Tampa Bay while Furtunato, then 29, was an older rookie reliever.

While Zambrano went a pedestrian 10-14 with a 4.42 ERA in parts of three seasons in New York, Kazmir (then just 20) was almost immediately thrust into Tampa Bay’s rotation (debut was August 23rd) and proved to be quite a catch. The left-hander went 55-44 with a 3.92 ERA in parts of seven seasons and was a big part of the team that turned the franchise around, when they made the World Series in 2008.

Furtunato, meanwhile, pitched in 15 relief appearances in 2004, missed all of 2005 with an injury, and was done after two appearances the following season. Kazmir, now 29, is 6-4 with a 4.11 ERA as a starter for Cleveland this season.

4. July 23, 2003—Pittsburgh trades Aramis Ramirez and Kenny Lofton to the Chicago Cubs for Jose Hernandez and prospects Matt Bruback and Bobby Hill.

This was more of an unusual lopsided trade deadline deal as Ramirez was just 25 and had a number of good years ahead of him as the Cubs’ third baseman. Even as late as last season, Ramirez hit .300 with 27 home runs, 50 doubles, and drove in 105 runs.

Lofton, then 36, hit .327 and stole 20 bases in 56 games as a nice top-of-the-lineup rental for the Cubs in 2003. Lofton and Ramirez helped lead Chicago to the playoffs before falling to Florida in seven games in the NLCS in what is remembered as the Steve Bartman series.

The Pirates, which did the deal as a salary dump and were never in the pennant race, got little help from any of the players in the deal. It’s just another reason why it’s taken them until now to become a contender again.

3. August 30, 1990—Houston trades reliever Larry Anderson to Boston for prospect Jeff Bagwell.

Anderson, 37 at the time, posted a 1.23 ERA in 22 innings for the first-place place Red Sox, which were summarily swept in the postseason by Oakland, featuring the Bash Brothers. He then signed with San Diego in the offseason and that was it.

For those insignificant 15 appearances, Boston gave up one of the greatest power-hitting first baseman of all-time in Bagwell, who would have made a awesome 1-2 punch with Mo Vaughn in the Red Sox’ lineup for most of the 90s. All in all, “Bags” hit 449 home runs, won the 1994 MVP, and had eight seasons of 30-plus home runs and 100-plus RBIs. The probable future Hall-of-Famer even won a Gold Glove award.

2. July 31, 1997—Boston trades reliever Heathcliff Slocum to Seattle for prospects Jason Varitek and Derek Lowe.

Seattle went on to make the playoffs in 1997 so they can be happy for that. But the then 31-year-old Slocum, who lasted just a year and a half with the Mariners (going 2-9 with a 4.97 ERA) was not much help. Even if they had traded just one of these prospects the trade would have been be lopsided.

Varitek would be Boston’s catcher for the next 14 seasons, earning three All-Star selections and eventually becoming team captain. Meanwhile Derek Lowe would earn 42 saves as the team’s closer in 2000 before becoming a 21-game winner as a starter in 2002. Both were integral parts of the Red Sox 2004 World Series-winning team, while Varitek was also part of the 2007 championship squad.

1. July 27, 2002—Cleveland trades Bartolo Colon and Tim Drew to Montreal for Lee Stevens, and prospects Cliff Lee, Bradon Phillips, and Grady Sizemore.

There’s not much redeemable about this deal for the Expos. They were just 51-53 at the time of the deal and finished 83-79—19 games behind the first-place Braves and 12 out of the wild card. To make matters worse, Montreal then flipped Colon to the White Sox that offseason, along with Jorge Nunez, for a washed-up Orlando Hernandez and unknowns Rocky Biddle and Jeff Liefer. Yikes.

For the Indians only Lee Stevens was of little use to them. Cliff Lee won a Cy Young Award in 2008, second baseman Brandon Phillips became a three-time All-Star in Cincinnati, and five-tool outfielder Grady Sizemore, who was a three-time All-Star would still be manning center field for the Indians had injuries not caught up to him.

Dave Martin
Dave Martin
Dave Martin is a New-York based writer as well as editor. He is the sports editor for the Epoch Times and is a consultant to private writers.