Worst Yankees Trades of the Decade

After compiling a list of the best Yankees trades of the past decade, Andrew has given me the honor of ranking some of the worst deals that the Yankees made this past decade. Here's what I came up with:

1. July 5, 2002 As part of a 3-team trade, traded Jason Arnold, John-Ford Griffin, and Ted Lilly to the Oakland Athletics. Received Jeff weaver from the Detroit Tigers. In addition, the Oakland Athletics sent a player to be named later, Frankly German, and Carlos Pena to the Detroit Tigers; and the Detroit Tigers sent cash to the Oakland Athletics. The Oakland Athletics sent Jeremy Bonderman (August 22, 2002) to the Detroit Tigers to complete the trade. This trade looked like a solid baseball trade for the Yankees. Jeff Weaver was regarded as one of baseball's young stud pitchers, with his nasty sinking fastball. He was only 25 at the time and locked up to a reasonable extended contract. Ted Lilly had shown promise in his year and a half in the Bronx but his stuff was not as good as Weaver's and Lilly never had the ace label that was commonly applied to Weaver. For the Yankees, they believed they were acquiring their next ace of the future. Unfortunately for the Yanks, it was Lilly who turned out to be the far more effective pitcher. Lilly went on to compile a .571 winning percentage from 2003-2009 and while he was never considered an ace, he certainly was considered more desirable than Jeff Weaver. Weaver's results were sporadic at best and when he gave up a game 4 World Series home run to Alex Gonzalez pitching in relief, the Yankees knew he had probably thrown his last pitch.

2. January 11, 2005 Traded Brad Halsey, Dioner Navarro, Javier Vazquez, and cash to the Arizona Diamondbacks. Received Randy Johnson. The Yankees had tried to acquire Johnson during the Summer of 2004 but were unsuccessful (apparently the Diamondbacks were not interested in Chien-Ming Wang and Robinson Cano). And the winter before, the Yankees were unable to acquire Arizona's other former ace, Curt Schilling. After being humiliated in the 2004 ALCS, the top of the Yankee hierarchy (specifically Randy Levine) made acquiring The Big Unit a priority. The Yankees finally worked out a deal for Johnson and said goodbye to Javier Vazquez, the pitcher who the Yankees so firmly believed would be their ace just one year prior that they promptly gave him a four year extension. Also gone was lower-end of the rotation lefty Brad Halsey and top catch prospect Dioner Navarro. Johnson was only a shadow of his former self, as he fought off constant nagging injuries. He pitched well in the second half of 2005, but was atrocious in his one start in the ALCS. He struggled all throughout 2006 and never came close to performing as expected. Vazquez pitched decently in his year with Arizona and then became a workhorse for Ozzie Guillen's White Sox. After being dealt to the Braves last off season, he posted what might be his best single season numbers in 2009, leading the NL with 238 strikeouts. Halsey stayed in the league for a few years with Diamondbacks and the A's, while Navarro was shipped to the Dodgers and then the Rays, where he was the starting catcher for the 2008 AL Champs. The Yankees may be able to salvage a bit of this deal, as they were able to reacquire Vazquez this winter.

3. December 13, 2003 Traded Brandon Weeden, Yhency Brazoban, Jeff Weaver, and cash to the Los Angeles Dodgers. Received Kevin Brown. The Yankees made this deal the day after Andy Pettitte left town for the Astros. Gone was enigmatic, but talented, Jeff Weaver, along with a few prospects who most of us had never heard of. In exchange, the Yankees received the oft-injured Kevin Brown, who was coming off a solid year in which he stayed healthy for the duration of the season. Brown was going to be depended on to be the team's ace coming into the year, replacing Roger Clemens. The results were far from Clemensesque. After starting off 5-0, Brown crumbled. His back eventually gave out and he made a trip to the DL. Upon returning, the results were much of the same as before and in an immature act of rage following a poor performance, he punched a wall with his non-pitching hand, breaking it. He would return to pitch in the postseason, where he was unable to do much against the Red Sox and put them in an early hole in the disastrous Game 7. 2005 wasn't much better for Brown, as he only managed to get through half of the season before shutting it down for good. Weaver, while he did not pitch well in New York, pitched well for the Dodgers from 2004-2005. He bounced around for the next couple of years, but helped the Cardinals win the World Series in 2006. Brazoban was electric during after his call up to the majors, but soon fought injuries and pitched a total of 9.2 innings since 2006.

4. June 13, 2001 Traded Damaso Marte to the Pittsburgh Pirates. Received Enrique Wilson. Not much to say about this one. The Yankees traded one of the better left-handed relievers of the decade for utility infielder who's only claim to fame was that he hit Pedro Martinez well. Wilson stuck with the Yankees through 2004, where in his final season he shared playing time at 2B with Miguel Cairo. The Yankees eventually reacquired Marte in 2008 and while the initial results were less than to be desired, his performance in the 2009 World Series has elevated his status significantly.

5. December 16, 2003 Traded Randy Choate, Nick Johnson, and Juan Rivera to the Montreal Expos. Received Javier Vazquez. The Yankees thought they were getting their next ace of the future (they had basically given up on Jeff Weaver taking on that roll). But to get Vazquez, the cost would be pricey. Gone was former top prospect Nick Johnson, who many believed was primed to have a breakout year. Juan Rivera had showed promise as well and Randy Choate had shown some ability to get left-handed hitters out. Vazquez put up solid numbers in the first half of 2004 and made an All-Star Appearance. However, an unspoken shoulder injury severely hampered his abilities during the second half. He was an abomination during the postseason and helped seal the deal for the Red Sox when on his first pitch of Game 7 in relief Johnny Damon hit his infamous grand slam. Johnson battled injuries for much of the past few years, but when healthy has been productive. Rivera was eventually dealt to the Angels and is now a very productive member of their outfield. Both Johnson and Vazquez are back with the Yankees so it will be interesting to see how they perform in their second stints.

6. July 12, 2000 Traded Jackson Melian, Drew Henson, Brian Reith, and Ed Yarnall to the Cincinati Reds. Received Mike Frank and Denny Neagle. The Yankees thought they were upgrading their rotation by acquiring Neagle and he briefly proved them right, starting out 2-0, including a complete game pitched against the Devil Rays. It simply went downhill from there, as he posted an ERA of close to 6.00. He pitched decently in the postseason but the Yankees wisely bid him goodbye after the season. Fortunately, Cincinnati received very little reward from this deal. None of the prospects traded made an impact and Drew Henson, a top prospect for the Yankees and multi-sport athlete, was dealt back to the Yankees, only to bomb out in both MLB and the NFL.

7. July 1, 2002 Traded Scott Wiggins to the Toronto Blue Jays. Received Raul Mondesi. The Yankees hosted the Mets the weekend before this deal was made. Due to various injuries and other circumstances, Joe Torre was forced to play infielder Enrique Wilson in RF. The results were disastrous. George Steinbrenner was livid and went out made a quick deal for the talented, but unpredictable Raul Mondesi. Mondesi was known as a gritty player with a powerful bad and a feared right-field arm. Unfortunately, he was also a free swinger and was incredibly moody. He contributed greatly to the strikeout department, swinging at almost everything he saw. After working with Reggie Jackson and putting up solid numbers during the first part of 2003, he soon found his way back to his old habits and was dealt prior to the trade deadline.

8. June 13, 2001 Traded D'Angelo Jimenez to the San Diego Padres. Received Jay Witasick/July 1, 2001 Traded Ricardo Aramboles to the Cincinnati Reds. Received Mark Wohlers. I am bundling these two deals into one since both of the players acquired were expected to fill the same role and neither one came close to doing so. The Yankees unwisely let Jeff Nelson walk after the 2000 season over a matter of nickels and dimes. His departure left a huge void in the Yankee bullpen. After Brian Cashman tried to fill the role with various journeymen auditioning on minor league contracts, he turned to the trade market, acquiring Witasick and Wohlers. Witasick had pitched well in relief for the Padres and with the emergence of Alfonso Soriano, the Yankees felt they could part with the once highly regarded D'Angelo Jimenez. Wohlers, the once elite closer for the Braves, had fallen far from his star status, struggling with his control and eventually with injuries. He had put up solid numbers for the Reds so Cashman took a shot. Neither pitcher managed to make a positive impact and simply made the loss of Nelson look ever so important. Wohlers was left to walk after the season and Witasick was dealt for outfielder John Vander Wal.

9. March 21, 2001 Traded Wily Mo Pena to the Cincinatti Reds. Received Michael Coleman and Drew Henson. The Yankees never really wanted to deal Drew Henson the summer before. Henson made it clear that in choosing between baseball and football, baseball only remained an option if he was going to be playing for the Yankees. The Reds were forced to make a deal to send Henson back to the Yankees. Henson appeared in 8 games for the Yankees and never managed to overcome his tendency to strike out. Michael Coleman contributed in the early part of 2001 before being cut. Wily Mo Pena had a high ceiling and was eventually dealt to the Red Sox for Bronson Arroyo.

10. July 31, 2004 Traded Jose Contreras and cash to the Chicago White Sox. Received Esteban Loaiza. Contreras, once known as "El Titan de Bronze" in his native Cuba, was the object of a bidding war between the Yankees and Red Sox during the Winter of 2002-2003. The Yankees won the bidding war (and rumor has it that newly appointed Red Sox GM Theo Epstein broke a window over this loss). Red Sox President Larry Luchino dubbed the Yankees with the infamous title of "The Evil Empire" after this incident. Perhaps the Red Sox should consider themselves lucky. Contreras showed the ability to look brilliant at times, but never looked comfortable, nor did he show the electric stuff that scouts had once spoken of. The Yankees finally gave up on him after a year and a half, dealing him veteran Esteban Loaiza. Loaiza had come off of a career year in 2003 but seemed to have lost whatever magic he had on his cut-fastball the year before. He performed poorly for the Yankees, losing his spot in the rotation. He pitched well in the ALCS, despite losing game 5. Contreras would go on to contribute to the 2005 World Champs and put up solid numbers the next season. He then tumbled into mediocrity, before finding his way as a reliever for the 2009 Wild Card Rockies.