MLB Trade Rankings: The 20 Worst Deadline Deals of the Last 25 Years

With the trade deadline fast approaching, it made me wonder—what are the worst trade deadline deals over the last 25 years?

Most fans can recall the best deals made at the deadline, like Cliff Lee to the Texas Rangers last year, but few can recall the worst deals unless their favorite team was on the wrong end of the deal.

If a trade is good or great, you know it right away. The bad trades sometimes can take years to see just how bad they were, especially if there were young players involved in the trade.

Here are what I think are the 20 worst trade deadline deals since 1986 (the last 25 years).

Most of the trades are considered bad because one team gave up a future Hall of Famer or a player that went on to greatness with their new team(s) while it got basically nothing in return.

Jason Schmidt for Armando Rios

In 2001, the Pittsburgh Pirates traded Jason Schmidt and John Vander Wal to the San Francisco Giants for Armando Rios and Ryan Vogelsong.

Schmidt would go on to finish second and fourth in Cy Young voting in 2003 and 2004, respectively, and make the All-Star team three times. He would also end up 78-37 with an ERA of 3.36, an ERA+ of 126 and 1,065 strikeouts in 1,069 innings pitched for the Giants.

What did the Pirates get out of Rios and Vogelsong? Pretty much nothing. Rios would play for two seasons for the Pirates before being released, and Vogelsong would play for five unproductive seasons.

Vogelsong is now back on the Giants after signing as a free agent this past offseason. He is currently 6-1 with an ERA of 2.17 and an ERA+ of 170 along with an All-Star appearance this season.

So not only did the Pirates give up a Cy Young candidate, Vogelsong waited to become the player they thought he could be until he was back on the Giants.

Jose Contreras for Esteban Loaiza

In 2004, the New York Yankees and Chicago White Sox traded starting pitchers (and cash).

The Yankees sent the inconsistent but still promising Jose Contreras to the White Sox and received Esteban Loaiza (who went 21-9 in 2003) in return.

Contreras would end up being a very serviceable pitcher for the White Sox, going 15-7 in 2005 and starting Game 1 of the World Series that season.

Loaiza wound up finishing 2004 for the Yankees in the bullpen and was granted free agency after the season.

While Contreras never lived up to his potential, at least the White Sox got several decent years out of him and ended up the "winner" in this trade.

Carlos Beltran in Three-Team Deal

In 2004, the Kansas City Royals knew they weren't going to be able to re-sign pending free agent Carlos Beltran.

Thus, at the trade deadline, the Royals, the Houston Astros and the Oakland Athletics worked a three-team deal that had Beltran (Royals) and John Buck (Athletics) go to the Astros, Octavio Dotel (Astros) end up on the Athletics and Mike Wood and Mark Teahen (Athletics) go to the Royals.

While Buck and Teahen would go on to start for the Royals, Dotel would be bounced around to several more teams. Beltran had one of the best postseasons ever in leading the Astros to the NLCS, and he got a huge free-agent deal with the Mets after the season.

The Athletics ended up being the biggest losers in this deal. The Astros benefited from the rental of Beltran. The Royals ended up being the "long-term winners" in this deal, but it still would have been better if they had been able to keep Beltran.

Aramis Ramirez for Jose Hernandez

In 2003, the Pittsburgh Pirates traded Aramis Ramirez and Kenny Lofton to the Chicago Cubs for Jose Hernandez, Matt Bruback and Bobby Hill.

Ramirez has been one of the Cubs' best players since the trade and is one of the best third basemen in the game today. Lofton was always a better than average player that always seemed to make the teams he was on better.

What did the Pirates get in return? Nothing.

This was just another trade in a long line of Pirates trades over the last 20 years that were made simply to dump talent for as little as possible in return, which the Pirates have become known for.

Grady Sizemore and Cliff Lee for Bartolo Colon

In 2002, the Montreal Expos traded Grady Sizemore, Cliff Lee, Brandon Phillips and Lee Stevens to the Cleveland Indians for Bartolo Colon and Tim Drew.

Sizemore has been the cornerstone for the Indians since the trade. Lee had a great 2008 for the Indians and won the Cy Young Award (he ended up being traded to the Phillies in 2009).

Phillips, after being a non-factor, was traded away to the Reds, where he is now one of the best second basemen in the game.

For the Expos, Colon had a fantastic finish to 2002 but was traded after the season.

This trade would have been made even worse for the Expos if the Indians kept Brandon Phillips instead of trading him away right before he became a star.

Joe Nathan and Francisco Liriano for A.J. Pierzynski

While technically this wasn't a deadline deal, the sheer one-sideness of the trade forced me to include it.

In November 2003, the San Francisco Giants traded Joe Nathan, Francisco Liriano and Boof Bonser to the Minnesota Twins for A.J. Pierzynski.

Nathan became one of the best closers in the game, and Liriano looked like an "ace in waiting" in 2006 until injuries derailed him (though he did through a no-hitter this season).

Pierzynski underperformed in San Francisco and was released by the Giants in 2004.

Normally you see a trade with this many minor league prospects (which is what Liriano et al. were) for a superstar-type player. Pierzynski was not that, batting .272 with an OPS+ of 86 for the Giants in 2004.

Scott Kazmir for Victor Zambrano

In 2004, the New York Mets thought they were one starting pitcher away from making the playoffs and decided to trade minor league prospects Scott Kazmir and Joselo Diaz to the Tampa Bay Rays for Victor Zambrano and Bartolome Fortunato.

Well, Zambrano was injured when the trade was made and only ended up making three starts for the Mets before being placed on the DL. He also went on to miss the entire 2006 season.

Kazmir became the ace of the young Tampa team, and even though he never fully lived up to his potential and hype and would later be traded to the Los Angeles Angels, the Rays truly pulled off a great trade.

The only thing keeping this one-sided trade from being ranked even higher is that Kazmir never fully panned out. Can you imagine if the Mets just kept Kazmir?

Provided they still traded for Johan Santana in 2008, their rotation could have been Santana, John Maine, Pedro Martinez and Scott Kazmir.

Sammy Sosa for Harold Baines

In 1989, the Texas Rangers sent Sammy Sosa, Wilson Alvarez and Scott Fletcher to the Chicago White Sox for Harold Baines and Fred Manrique.

Baines was purely a designated hitter and didn't provide anything to the Rangers, and he was traded to the Athletics in 1990 for the dreaded "player to be named later." Manrique only played 54 games for Texas before being traded away in 1990.

In Alvarez' first start for the White Sox (and his second career start overall), he threw a no-hitter in 1991, but other than that, he was inconsistent.

We all know what happened to Sammy Sosa. While he underperformed for the White Sox, what he did when he joined the Chicago Cubs several years later is what makes this trade bad for the Rangers.

Sosa would go on to hit 50 or more home runs in four straight years (three times he surpassed 60 HR for the season). Granted, this was at the height of the steroid era, but if Texas simply held on to Sammy, its playoff results in the late 1990s might have been different.

Curt Schilling for Mike Boddicker

In 1988, the Boston Red Sox traded a minor league prospect named Curt Schilling and a rookie named Brady Anderson to the Baltimore Orioles for Mike Boddicker.

The Boston Red Sox were looking for a starting pitcher, so they decided to trade for Boddicker. In the two-and-a-half seasons Boddicker was on the Red Sox, he went 39-22 with an ERA of 3.49, an ERA+ of 118 and a WHIP of 1.311.

While Anderson would later be named in the Mitchell Report, he was a consistent outfielder for the Orioles for 14 seasons. Schilling would go on to lead the Diamondbacks to the World Series title in 2001 and upon his return to Boston did the same for the Sox.

This trade makes the list simply due to the ineffectiveness of Boddicker on the Sox and what Schilling would end up doing elsewhere before being brought back.

Curt Schilling for Travis Lee

In 2000, the Phillies traded Curt Schilling to the Arizona Diamondbacks for Travis Lee, Omar Daal, Nelson Figueroa and Vicente Padilla.

Schilling would finally find his stride in Arizona, leading the Diamondbacks to a World Series title in 2001 (along with Randy Johnson) and finishing second in Cy Young voting in back-to-back years.

Lee never lived up to his hype and potential. Daal and Figueroa were basically journeyman pitchers for their entire careers. Padilla became the only piece of value the Phillies got in this trade until injuries started to affect him.

Michael Young for Esteban Loaiza

In 2000, the Toronto Blue Jays traded a young prospect named Michael Young (along with Darwin Cubillan) to the Texas Rangers for Esteban Loaiza.

Why Loaiza was always part of deadline deals is beyond me. For the Blue Jays in three seasons, he went 25-28 with an ERA of 4.96 and an ERA+ of 95.

Young has simply become one of the best Texas Rangers in that franchise's history while posting (so far) a career batting average of .301 and an OPS of .798 along with multiple All-Star game appearances.

David Cone for Marty Janzen

In 1995, the Toronto Blue Jays traded David Cone to the New York Yankees for Jason Jarvis, Mike Gordon and Marty Janzen.

Only Janzen made it to the major league level, but in only 27 games spread over two seasons (was a starter and reliever).

David Cone became the heart and soul of the Yankees pitching staff that saw that franchise re-emerge as the best franchise in baseball. In 1995, Cone went 9-2 down the stretch and helped the Yankees reach the postseason for the first time since 1981.

Cone would go on to win four World Series championships with the Yankees and even threw a perfect game.

Randy Johnson for Mark Langston

In 1989, the Montreal Expos were in the hunt for the division title when they traded a young and wild Randy Johnson (along with Gene Harris and Brian Holman) to the Seattle Mariners for Mark Langston.

Langston did very well for the Expos in 1989, going 12-9 with a 2.39 ERA and an ERA+ of 148. However, he would leave the Expos in December 1989 as a free agent.

Randy Johnson simply then went on to become one of the most dominant pitchers in baseball history for the Mariners, Astros, Diamondbacks, Yankees and Giants.

Randy Johnson for Freddy Garcia

In 1998, the Mariners realized they probably wouldn't be able to re-sign Randy Johnson, so they sent him to the Astros for Freddy Garcia, Carlos Guillen and "a player to be named later," who turned out to be John Halama.

Freddy Garcia was a pretty good pickup for the Mariners. He went 76-50 with a 3.89 ERA and a third-place Cy Young finish over six years for the Mariners. Carlos Guillen didn't succeed in baseball until he joined the Tigers in 2004. John Halama was basically ineffective.

For the Astros, Johnson went 10-1 with a 1.28 ERA and got the Astros to the playoffs. He would then leave as a free agent after the 1998 season.

While Garcia was better for the Mariners long-term, and they might have lost Johnson as a free agent anyway, trading away one of the most dominant pitchers in baseball history at the beginning of his best years is simply a mistake.

Jay Buhner for Ken Phelps

As a Yankees fan, I have to agree with George Costanza from Seinfeld when he asked George Steinbrenner, "How could you have traded Buhner for Ken Phelps? Ken Phelps!"

That's what happened in 1988. Steinbrenner was looking for a hitter that would help the Yankees win the American League East, so he traded Jay Buhner and two minor league players to the Seattle Mariners for Ken Phelps.

Phelps would help the Yankees finish fifth in the AL East while batting .224. Over his two seasons in New York he batted .240 with 17 home runs.

Buhner simply became a fan favorite in right field for the Mariners and batted .255 with 307 home runs over 14 seasons.

Fred McGriff for Melvin Nieves

In 1993, the San Diego Padres traded Fred McGriff to the Atlanta Braves for Vince Moore, Donnie Elliott and Melvin Nieves.

Moore never made it out of the minors, and Elliott pitched in 31 games over two seasons. Nieves played in 127 games over three seasons for the Padres.

McGriff simply went on to become one of the most consistent hitters in the 1990s, helping the Braves reach the playoffs in the five seasons he spent with them.

For the Braves, he batted .293, had an OPS+ of 128 and hit 130 home runs.

Derek Lowe and Jason Varitek for Heathcliff Slocumb

In 1997, the Seattle Mariners needed bullpen help, so they sent Derek Lowe and Jason Varitek to the Red Sox for Heathcliff Slocumb.

Slocumb would only last for two seasons in Seattle, over which he went 2-9 in 84 games with an ERA of 4.97 and a WHIP of 1.635.

Lowe would go on to win 21 games for the Red Sox in 2002 and be an integral part of the World Series championship in 2004. 

Varitek is still on the Red Sox and has been their captain and inspirational leader. While he's never been a superstar offensively, the way Varitek handles the pitching staff and provides guidance and leadership to the team simply can't be denied.

In my opinion, this is one of the best trades the Red Sox have ever made in their history (sadly, they have almost made some of the worst trades in history as well).

Mark McGwire for T.J. Mathews

In 1997, Mark McGwire's contract was going to expire, and the Oakland Athletics didn't think they could re-sign him, so they sent him to the St. Louis Cardinals for Eric Ludwick, T.J. Mathews and Blake Stein.

None of the players the Athletics got ever amounted to anything (at least not on that team).

McGwire simply went on to hit 24 home runs over the rest of the 1997 season. He would then go on to hit 196 more over the next four years before retiring (and admitting to steroid use).

This trade is ranked so high because the Athletics got absolutely nothing, while McGwire went on to have one of the best four-year offensive stretches in baseball history.

John Smoltz for Doyle Alexander

This trade happened just after the trade deadline in 1987. The Detroit Tigers were looking for a proven starter and sent minor league prospect John Smoltz to the Atlanta Braves for Doyle Alexander.

Alexander went 9-0 over 11 starts with a 1.53 ERA to help the Tigers reach the ALCS. However, over the next two seasons, he went 20-29 and then retired.

Smoltz went on to join Greg Maddux and Tom Glavine in the creation of one of the best starting rotations in baseball history (if not the best).

Over 20 seasons on the Braves, Smoltz won one Cy Young Award and had 210 wins, 154 saves, a WHIP of 1.170 and an ERA of 3.26.

If the Tigers only knew how Smoltz's career would finish, you can bet they would have traded in the ALCS appearance for the next 20 years of having Smoltz on the mound.

Jeff Bagwell for Larry Andersen

This trade occurred after the July deadline in 1990 (August 1990). The Red Sox were looking for bullpen help to win the American League East, so they sent Double-A third base prospect Jeff Bagwell to the Houston Astros for Larry Andersen.

Andersen would appear in 15 games for the Red Sox and had a WHIP of 0.955 and an ERA of 1.23. However, he would leave the Red Sox as a free agent following the 1990 season.

Jeff Bagwell simply became one of the most feared hitters in the 1990s and over his 15 seasons for the Astros batted .297 with an OPS of .948, an OPS+ of 149 and 449 home runs. Bagwell (provided he's not caught up in the steroid era suspicion) should be in the Hall of Fame.

So what do you think? Did I rank a trade too high or too low? Did I forget any deadline deals that were worse than the ones I listed? Please feel free to comment below.