Looking at some of the Yankees worst moves of the 2000’s


  1. Carl Pavano: Four Year, $39.95 Million, 2004

If you ask Yankee fans for their list of their most hated players in franchise history, a good chunk of fans would include Pavano. Coming off of an All-Star season in 2004 and nine innings of one-run ball against the Yankees in the 2003 World Series, Pavano was expected to come in and be the new ace of the New York Yankees. While his first season started well in the Bronx, with a 4-2 record and 3.69 ERA in his first ten starts, he finished the season making 17 total starts due to a left shoulder injury, and went 0-4 the rest of the year, with his ERA rising to 4.77. Pavano then missed all of the 2006 season with a bruised buttocks, as well as broken ribs that were suffered in an automobile accident while Pavano was driving his Porsche, an injury he neglected to tell the Yankees about for two weeks when he was supposed to come off the DL. In 2007, Pavano started opening day for the Yankees, but made only two starts on the season, giving up six runs in 11.1 innings before opting for Tommy John Surgery. After coming back from the procedure in 2008, Pavano remained ineffective, with a 5.77 ERA and 1.485 WHIP in seven starts, leaving his last start as a Yankee with a “left hip injury” to a shower of boos. In his four years with the Yankees, Pavano made a total of 26 starts, going 9-8 with a 5.00 ERA and 1.455 WHIP, earning the nickname “American Idle” from the New York media, and becoming widely regarded as one of the worst Yankees in franchise history.

  1. Jaret Wright: Three Years, $21 Million, 2004

Coming off of a stellar 2003 with the Braves, where he went 15-8 with a 3.28 ERA in 186.1 innings pitched, the Yankees brought in Wright alongside Pavano to solidify their rotation. And like Pavano, he was a huge flop in New York, with shoulder injuries limiting him to 13 terrible starts in 2005, where he went 5-5, but with a 6.08 ERA and 1.775 WHIP. The next season was more of the same; while Wright did appear in 30 games, winning eleven of them, he only pitched in 140.1 innings across 27 starts and did so with a 4.49 ERA and 1.525 WHIP. In the offseason, Wright was traded to the Orioles for Chris Britton and cash considerations, putting an unceremonious end to his Yankee career. Unlike Pavano, this flop could have likely been predicted, as from 1998 to 2003, Wright pitched a total of 480 innings (80 per season) with a 5.94 ERA, making it likely 2004’s success came as a result of Atlanta Braves pitching coach Leo Mazzone, widely regarded as the greatest pitching guru of all time.

  1. Kei Igawa: Five-Year, $20 Million, $26 million posting fee, 2006

The Yankees attempt to answer the Red Sox signing of Daisuke Matsuzaka, Igawa cost the Yankees a total of $46 million, after having to pay $26 million for the right to negotiate with the Hanshin Tigers. In his major league debut on April 7, 2007, Igawa gave up seven runs in five innings, a sign of things to come for his stint in Pinstripes. Igawa spent most his time with the Yankees in AAA, being demoted in 2007 after going 2-3 with a 6.25 ERA and 1.670 WHIP in 14 starts in the majors, and failing to make the team out of spring training in 2008. After being recalled in 2008, Igawa gave up eleven hits and six runs in his lone start of the season, before clearing waivers and being removed from the 40-man roster in July of that year. Igawa refused to return to Japan twice when Brian Cashman attempted to sell him back to a Japanese team, and although he set the record for career wins as a Scranton/Wilkes-Barre Yankees, he made a total of sixteen appearances for the Yankees, finishing his career with a 2-4 record, 6.66 ERA, and 1.758 WHIP, costing the Yankees almost $3 million per appearance.

  1. Javier Vazquez

    worst yankees moves
    The Yankees were burned by Javier Vazquez twice.

    (1): Traded to Yankees for Nick Johnson, Juan Rivera, and Randy Choate, 2003

Despite a strong first half where made an All-Star team in 2003, Vazquez finished his first year in pinstripes with a 4.91 ERA and 1.288 WHIP across 32 starts, although he did win 14 games. Vazquez lands on this list for the first time mainly because of his performance in Game 7 of the 2004 ALCS, where the Yankees became the first team in sports history to blow a 3-0 lead in a best of seven series. Coming in as a relief pitcher, Vazquez walked five batters and gave up three runs to put the Red Sox up 6-0 in the second inning, including two home runs to Johnny Damon. Additionally, from 2004-06, Nick Johnson hit .282/.407/.479 with the Expos/Nationals, with Juan Rivera hitting .298/.349/.484 over the same time frame, making the trade even worse from the Yankees perspective.

  1. Javier Vazquez (2): Traded to the Yankees with Boone Logan for Melky Cabrera, Mike Dunn, and Arodys Vizcaino, 2009

Not learning from their first mistake, the Yankees again acquired Vazquez for the 2010 season, and again he severely underachieved, going 10-10 with a 5.32 ERA and a 1.398 WHIP in a near career low 157.1 innings pitched. Vazquez pitched poorly enough for the Yankees for him to be moved to the bullpen for parts of the regular season and the postseason, and he tied a major league record by hitting three batters in a row against the Rays. At the season’s end, the Yankees released Vazquez. With Atlanta, Mike Dunn became one of the better left-handed relief pitchers in baseball with a 1.89 ERA in 25 games, and Melky later went on to become an All-Star with the Giants and may have prevented the Yankees from signing Jacoby Ellsbury to a huge contract later on. The one positive of this trade was the Yankees acquiring Boone Logan, who as the team’s LOOGY went 19-7 with a 3.38 ERA in 256 games.

  1. Roger Clemens: One-Year, $18.7 Million, 2007

After retiring with the Astros following the 2006 season, the Rocket suddenly appeared in the owner’s box at Yankee Stadium on May 6, 2007, where it was announced that the 45-year-old right-hander had agreed to a pro-rated one-year deal worth $28 million, which ended up being worth $18.7 million. Clemens’ contract paid him $4.7 million per month and over $1 million per start, and it was clear that old age had caught up with one of the game’s greatest pitchers of all time. In 17 starts, Clemens went 6-6 with a 4.18 ERA and 1.313 WHIP, a far cry from his career norms. The final image fans had of Clemens on a big league mound was his limping off the field in the third inning of Game 3 of the ALDS with a hamstring injury, putting a sad end to one of the greatest careers the game had ever seen.

  1. Alex Rodriguez: Ten Years, $275 Million, 2008

When Rodriguez opted out of his contract following the 2007 season, the Yankees signed him to the largest contract in sports history, which would keep him in New York through his age 41 season. Let’s start by saying the Yankees don’t win the 2009 World Series without Rodriguez; in the regular season, he hit .286/.402/.532 with 30 HR and 100 RBI, before hitting 6 HR with 18 RBI in the postseason, with an OPS above .973 in all three of the Yankees series. Now to the bad; Rodriguez missed the entire 2014 season due to his role in the Biogenesis PED scandal. Rodriguez played over 140 games only once over the length of his contract, including only 44 in 2013. Statistically, his seasonal averages were 22 HR, 73 RBI, .369/.359/.486 in 110 games; decent numbers, but nowhere near the kind of production expected out of the highest-paid player in baseball. In 2016, the Yankees released Rodriguez after 65 games but were still on the hook for paying him the rest of his $21million contract in 2016, and another $21 million in 2017 for him to go work for Fox Sports. While it was fair for the Yankees to bet on a then 31-year-old Rodriguez coming off his third AL MVP, this contract may go down as one of, if not the worst in baseball history, crippling the Yankees payroll for years.

  1. Kevin Brown: Traded to Yankees for Jeff Weaver, Yhency Brazoban, Brandon Weeden and $2.6 Million Cash, 2004

By the time the Yankees acquired the once ace right-hander, Brown was nearing his 39th birthday, yet was expected to be a front-line starter for the Yankees in 2004. The Yankees paid Brown over $15 million a season in 2004 and 2005, and he responded by posting a 4.09 ERA and 1.265 WHIP in 22 starts in 2004, missing time in September after breaking his left hand punching a wall in the clubhouse and ending his regular season. While Brown did pitch well in the 2004 ALDS, getting a win against the Twins with six one-run innings, he became infamous in Yankees lore for his performance in the 2004 ALCS, where he went 0-1 with a 21.60 ERA in two starts, lasting a total of 3.1 innings and giving up nine runs. In the deciding Game 7, Brown got the start and preceded to give up five runs in 1.1 innings, including a monster two-run home run to David Ortiz. 2005 was more of the same from Brown, as injuries limited him to 13 ineffective starts, where he went 4-7 with a 6.50 ERA and 1.718 WHIP; at season’s end, he announced his retirement, putting an end to the career of one of the most unlikable Yankees in recent memory.

  1. Jose Contreras: Four Years, $32 Million, 2002

Signed from right under the Red Sox, Contreras was supposed to be the next big pitcher in baseball after defecting from Cuba in 2002, having been named Cuban Athlete of the Year on three separate occasions. The Yankees paid him as such, and while on the surface, his first year in Pinstripes was a success with a 7-2 record, 3.30 ERA, and 1.155 WHIP, he only made 9 starts in 18 total appearances, pitching only 71.0 innings due to spending two months on the DL with a subscapularis strain, and four stops in the minor leagues. In the 2003 ALCS and World Series, Contreras had ERAs of 5.79 and 5.68 respectively, giving up 7 runs in eleven innings pitched, and walking seven while taking a loss in both series. Before being traded to the White Sox at the 2004 trade deadline, Contreras spent 16 days in the minor leagues in May, and had a 5.64 ERA and 1.411 WHIP in 18 starts, ending his Yankee career by only making 27 starts, with a total of 166.2 innings pitched, and a 4.64 ERA and 1.302 WHIP. In Contreras’ case, he did not come anywhere near justifying his hype or the contract the Yankees gave him and quickly went from being the savior of the Yankees rotation to being traded within a year and a half.

  1. Pedro Feliciano: Two Years, $8 Million, 2011

This contract isn’t so much about the money; $8 million is chump change for the Yankees and the Steinbrenner family. Rather, it is about how Feliciano did not make a single appearance for the Yankees over the life of his contract due to arthroscopic surgery to repair a torn capsule in his left throwing arm, and an additional surgery during the 2011 offseason. From 2007-2010, Feliciano made 344 relief appearances for the Mets, the most over a four-year span in MLB history, and led the MLB in appearances from 2008-10. This was the likely cause of the injury, and it caused the Yankees to throw $8 million completely down the drain for zero on-field results.

  1. Kevin Youkilis: One Year, $13 million, 2012

Signed to help an aging Alex Rodriguez at third base for the 2013 season, the former All-Star was hampered by back injuries, being placed on the 15-day DL on April 30, 2013, with a back strain. After missing a month, he returned to the field on May 30 but was again forced to return do the DL on June 14. By June 20, Youkilis’ season was finished after undergoing season-ending surgery to repair a herniated disk in his back. All told, The Greek God of Walks played a total of 28 games in pinstripes, making almost $500,000 per game, and hitting .219/.305/.343 with only 2 HR and 8 RBI in 118 plate appearances, a far cry from his days with the Red Sox.



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