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New York Yankees: Ranking the 10 Worst Trades in Bombers History

Doug RushSenior Analyst IJanuary 12, 2017

New York Yankees: Ranking the 10 Worst Trades in Bombers History

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    One of my favorite times during the baseball season is the trade deadline.

    Ever since I could remember, I always liked all the action, the rumors and the debates you would hear on which players teams should try to get—especially when people talked about the Yankees in trade rumors.

    We all know the Yankees' names get brought up in a dozen or so rumors every July, and as we have seen in their history, they've made a lot of deals.

    Some were good, and some weren't so good.

    This list is to rank the 10 worst trades that the Yankees have made in their history.

10. Armando Benitez

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    July 16, 2003: The Mets trade Armando Benitez to the Yankees in exchange for Ryan Biconda, Jason Anderson and Anderson Garcia.

    I put this one on the list because quite frankly, getting Armando Benitez made absolutely no sense whatsoever.

    Benitez was hated in the Bronx for the time he drilled Tino Martinez in the back with a pitch after serving up a couple of home runs while he was on the Orioles—which then started a full-out brawl between the two teams.

    Benitez was also a very un-clutch closer for the Mets who they had grown tired of, so in 2003, the Yankees tried him out as Mariano Rivera's setup man.

    Benitez posted a 1.93 ERA in nine appearances, striking out 10 batters and walking six.

    But then on August 6, 2003, just three weeks after landing him, the Yankees shipped out Benitez to the Mariners in exchange for Jeff Nelson.

    To this day, I still don't know why the Yankees ever took Benitez to begin with.

9. Raul Mondesi

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    July 1, 2002: The Toronto Blue Jays trade Scott Wiggins to the Yankees for Raul Mondesi.

    The Yankees really needed a right fielder, especially after Paul O'Neill retired following the 2001 season.

    So Brian Cashman made a trade with the Blue Jays to land Raul Mondesi.

    Mondesi used to be a 30 home run, 90 RBI guy who could play solid defense. But by the time Mondesi hit his 30's, he wasn't the same player and his skills were diminishing.

    He hit .241 with 11 home runs and 43 RBI during the second half of the 2002 season for the Bombers; he only hit .250 with one RBI in the ALDS against the Angels.

    In 2003, Mondesi was hitting .258 with 16 home runs and 49 RBI, but had fallen out of favor with the Yankees because of his bad attitude and was traded to the Diamondbacks on July 29, 2003.

8. Kevin Brown

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    December 13, 2003: The Los Angeles Dodgers trade Kevin Brown to the Yankees in exchange for Jeff Weaver, Yhency Brazoban and Brandon Weeden.

    I remember how much I liked this trade because it got Jeff Weaver out of town and brought in an established name like Kevin Brown to the Bronx.

    Only Brown was 39 years old and a shell of what he used to be.

    Brown did start off the 2004 season pitching well with a 10-4 record; that was until he punched a wall on September 3, 2004 and broke his hand, which forced him to miss most of the rest of the season, but he did return for the playoffs.

    Brown was fine in the ALDS against the Twins and even picked up a win for the Yankees in that series.

    But against the Red Sox in the ALCS, he was awful.

    In Game 3 at Fenway Park, Brown lasted just two innings, after allowing four runs and five hits.

    But his doom was Game 7 at Yankee Stadium with the series tied 3-3. Brown only lasted 1.1 innings and put the Yankees behind 2-0 in the first inning. In the second inning, Brown had walked the bases loaded before Joe Torre yanked him out of the game to put in Javier Vazquez, who, in the next at-bat, served up a grand slam to Johnny Damon, making it 6-0 Boston.

    Brown was supposed to be a big-game pitcher, but he was anything but that with the Yankees, especially in the ALCS when the Yankees could have used one more big game out of him.

7. Jeff Weaver

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    July 5, 2002: The Oakland A's acquired Ted Lilly, Jason Arnold and John-Ford Griffin. The Detroit Tigers acquired Carlos Pena, Franklyn German and Jeremy Bonderman. The Yankees acquired Jeff Weaver.

    At the time of the trade, Jeff Weaver was a 25-year-old strikeout pitcher with a ton of potential, and as the Yankees fifth starter in 2002, he could learn under a great staff.

    But Weaver never lived up to the potential and would have more meltdowns on the mound.

    In 2003, he went 7-9 with a 5.99 ERA before being sent to the bullpen. In Game 4 of the 2003 World Series against the Florida Marlins, Weaver served up the walk-off home run to Alex Gonzalez—a game that could have put the Yankees ahead 3-1 in the series, but instead, made it 2-2.

    Weaver was then sent away two months later to the Dodgers and had two decent seasons for Los Angeles, but clearly, we are all aware that his younger brother is the better overall pitcher.

    If only the Yankees didn't give up on Ted Lilly so soon.

6. Mike Lowell

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    February 1, 1999: The Florida Marlins acquire Mike Lowell in exchange for Todd Noel, Mark Johnson and Ed Yarnall.

    At the time, the Yankees had Scott Brosius as the starting third basemen, but clearly, the Yankees had no idea what they were giving up in Mike Lowell.

    With the Marlins, Lowell was a solid 25 home run, 100 RBI guy and helped them win the 2003 World Series over the Yankees.

    In 2006, Lowell was a throw-in that the Marlins wanted to get rid of in the trade that sent Josh Beckett to the Red Sox in exchange for Hanley Ramirez and Anibal Sanchez.

    Lowell continued to put up solid numbers while in Boston and helped them win the 2007 World Series.

    If only the Yankees waited two more seasons after Brosius retired, they could have seen what Lowell was capable of.

5. Jay Buhner

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    July 21, 1988: The Yankees trade Jay Buhner and Rich Balabon to the Seattle Mariners in exchange for Ken Phelps.

    What's one of the most famous quotes in Seinfeld from Frank Costanza?

    "What the hell did you trade Jay Buhner for?"

    It not only ranks up as one of the worst trades in Yankees history, but in baseball history as well.

    Jay Buhner was a 23-year-old prospect that was on the verge of his career starting, but the Yankees had to have the established star, so Buhner was sent packing.

    Ken Phelps was a 33-year-old veteran for Seattle who had 14 home runs and 32 RBI while hitting .284.

    With the Yankees in the second half, he hit just .224 with 10 home runs and 22 RBI. Total bust.

    All Buhner did was go on to play 13 seasons in Seattle, hit 310 career home runs and become a staple in the Mariners lineup until 2001.

    Another prospect that the Yankees let get away too soon.

4. Esteban Loaiza

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    July 31, 2004: The Yankees send Jose Contreras to the Chicago White Sox in exchange for Esteban Loaiza.

    The Yankees needed pitching depth for the second half of the season and Jose Contreras simply was not cutting it with the Yankees.

    So at the trade deadline, the Yankees sent Contreras to the White Sox and got back all-star Esteban Loaiza.

    Loaiza had won 21 games and finished second in the AL Cy Young voting, but people wondered why Chicago gave him up for so little.

    Whether it was the pressure of pitching in New York or the league figured him out, he was dreadful for the Yankees.

    Loaiza went 1-2 with a 8.50 ERA in six starts before they buried him into the bullpen as a mop-up reliever.

    Contreras, on the other hand, went on to help the White Sox win the 2005 World Series the following season.

    Contreras was never cut out to pitch in New York, but trading for Loaiza was an even bigger mistake by Brian Cashman.

3. Javier Vazquez

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    December 16, 2003: The Montreal Expos trade Javier Vazquez to the Yankees in exchange for Nick Johnson, Juan Rivera and Randy Choate.

    December 22, 2009: The Atlanta Braves trade Javier Vazquez to the Yankees in exchange for Melky Cabrera, Mike Dunn and Arodys Vizcaino.

    Javier Vazquez makes the top three because the Yankees didn't trade for him once, but twice.

    The first time, Vazquez was a 27-year-old up-and-coming pitcher who was brought in to fill the void Andy Petitte left when he departed to Houston.

    In the first half of the season, Vazquez was sensational, posting a 10-5 record before the break. In the second half, the legs fell off and he finished 4-5 and had his ERA shoot up from a 3.86 to 4.91.

    In Game 7 of the ALCS, we all remember Vazquez serving up the grand slam to Johnny Damon in the second inning that slammed the door on the series, and three months later, Vazquez was a part of the deal that landed Randy Johnson.

    Five years later, Vazquez was re-acquired from the Braves and everyone thought the deal was a steal. WRONG!

    Vazquez again was terrible for the Yankees, posting a 10-10 record and a 5.32 ERA. Vazquez was banished to the bullpen and wasn't used in the ALDS or ALCS.

    Just think, the Yankees could still have Melky Cabrera, who is tearing it up in San Francisco.

2. Willie McGee

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    October 21, 1981: The Yankees trade Willie McGee to the St. Louis Cardinals in exchange for Bob Sykes.

    I really want to know, who thought of this trade?

    The Yankees had Willie McGee stashed away in the minor leagues, but decided to trade him to the Cardinals for pitcher Bob Sykes.

    Sykes would not play for the Yankees, nor play in baseball ever again after the 1981 season.

    McGee, on the other hand, won the 1982 Rookie of the Year Award, won the 1985 NL MVP Award and helped the Cardinals win the 1982 World Series.

    McGee also helped St. Louis get to the 1985 and 1987 World Series as well as the Oakland A's in the 1990 World Series.

    It just baffles me that the Yankees gave away McGee for a guy who did not pitch ever again in the majors.

1. Fred McGriff

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    December 9, 1982: The New York Yankees trade Fred McGriff, Dave Collins and Mike Morgan to the Toronto Blue Jays in exchange for Dale Murray and Tom Dodd.

    I give this the No. 1 worst trade spot because the Yankees gave away a player who is a borderline Hall of Famer.

    Dale Murray was a reliever who was nothing special or spectacular and Tom Dodd barely saw the Major Leagues.

    McGriff, on the other hand, hit 493 career home runs, was a five-time All-Star and helped the Braves win the 1995 World Series.

    McGriff also helped the Braves get to the 1996 World Series.

    Sure, the Yankees had Don Mattingly as their starting first baseman, and in his prime, Mattingly was one of the best in baseball.

    But if they had held onto McGriff, they could have found a spot for him in the lineup. Or they could have at least found a better package to deal him for.

    To me, trading away a borderline Hall of Famer and getting nothing back in return ranks as the worst trade in Yankees history.

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