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The New York Yankees' 20 Biggest Mistakes Since 2000

The New York Yankees are the greatest franchise in the history of the MLB. With their 27 World Series titles and plethora of legends, they are one of the best sport teams in every professional sport. With that being stated, it is apparent that they have made some wonderful decisions with their rosters over the entirety of their franchise’s history. Yet, the 2000s have not been perfect for this team, as they have made some questionable decisions that have set them back a bit over the years. That is not to take away from the fact that they have won two World Series titles so far in this century, but they could have had far more if they have avoided some drastic mistakes during their golden days.

With all that has been stated thus far, in this article, we will be looking at the twenty worst moves made by the Yankees since the start of the 2000s. The moves that will be discussed have haunted Yankee fans for quite sometime and will never be erased from their memories. It is important to note that a big reason behind these mistakes is their abundance. The Yankees have and will always have an upper hand on all other MLB teams when it comes to signings because of their budget, but also their immense success. Everyone dreams of playing there. However, they have learned that money does not always deliver results.

Nonetheless, let’s look at the twenty worst moves the Yankees have made since 2000!

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20 Signing Randy Johnson

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Randy Johnson is one of the greatest pitchers in the history of the MLB, so naturally, he had a stint with the Yankees. Johnson signed with the Yankees following their disappointing finish to the 2004 season. They thought that they had landed themselves the ace that would carry them past the Red Sox again.

However, when you look at Johnson’s overall tenure with the Yankees, it was not very impressive.

He reached expectations, just barely, during his first season. However, his second season was atrocious and saw him post an ERA over 5.00. Given the fact that he landed a monster deal, this signing was a bust.

19 Robinson Cano’s Replacement: Brian Roberts

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When Robinson Cano left the Yankees to sign with the Mariners, it was devastating for them. Cano was supposed to be their next franchise player for years to come, but he took the money and ran elsewhere. With the Yankees wanting to stay in contention, they signed Brian Roberts as his replacement.

Roberts was a very good player with the Orioles, but with the Yankees, he was way out of his prime.

Roberts was a terrible signing because he struggled and slowed down the inevitable rebuilding phase the Yankees desperately needed. Roberts would end up leaving shortly after without much success.

18 The Jose Contreras Signing

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Jose Contreras was the top international free agent on the market when the Yankees signed him to his massive contract. Contreras was expected to develop into an absolute superstar in the league, so he had a ton of teams interested. With the rival Sox wanting him, the Yankees overpaid him.

Contreras would soon fail to reach expectations and progressively got worse as the months passed by.

There was a lot of criticism about the signing, as Contreras failed to pitch even at the league average, as displayed by his insanely high ERA and hit totals. They eventually would trade him to the White Sox.

17 Signing Kevin Youkilis

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Kevin Youkilis was once a superstar with the Yankees’ biggest rivals, the Boston Red Sox. He was a very solid hitter, but was an even better fielder, as displayed by his multiple gold glove awards. However, everything quickly changed when the Red Sox traded him and started their rebuild.

In 2013, the Yankees surprisingly signed Youkilis.

Youk had some serious past troubles with the Yankees due to the rivalry, but he was a good teammate there. However, his stats fell off dramatically with the Yanks and was nothing close to the $12 million he was given.

16 Alex Rodriguez (Opt Out Extension)

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No matter how much Alex Rodriguez is hated, he is one of the best baseball players in the history of the MLB. His tenure with the Yankees was controversial, but he did lead them to a World Series and was worth the money, especially for giving up basically nothing to bring him to the club.

Yet, the part where the Yankees messed up with him was giving him another ten-year deal when he was already 32.

As we clearly saw, A-Rod would not come close to finishing this contract, as his play fell off dramatically in his final season with the club. Nonetheless, he should still have love from New York for his efforts.

15 Raul Mondesi Trade

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During his prime seasons in the MLB, Raul Mondesi was a legitimate all-star and a five-tool player. However, when the Yankees decided to trade for him in 2002, he definitely was on the verge of a clear decline in skill. However, they decided to take a risk on the former star outfielder.

Mondesi would end up being a horrible fit with the Yankees for multiple reasons.

Due to the fact that his play dropped, the trade already was a bust. However, his poor attitude would be the final cherry on top of his tenure and resulted in him getting traded once again just one year later.

14 Signing Travis Hafner

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During his prime years, Travis Hafner was the power hitter of the Cleveland Indians and a spectacular player. However, as soon as Hafner started to get a lot of recognition for his play, he ended up having serious injury troubles and eventually was let go by the Indians because of this apparent fact.

The Yankees decided to give Hafner a chance and signed him in hopes that he would be their DH.

However, his time with the Yankees was absolutely horrid and injury filled.

He managed to hit just above the Mendoza line and his power numbers also took a slight dip. This would be his last season ever too.

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13 Armando Benitez Trade

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Armando Benitez was the star closer of the New York Mets during the late 90s and early 2000s. He was a big reason why the Mets made it to the World Series, before losing to the Yankees. He also was hated immensely by Yankee fans because he notoriously hit Tino Martinez, which led to a brawl.

In 2003, Benitez would shockingly be traded to the Yankees.

This definitely was a move that was met with some criticism by fans because there was already a lot of animosity with him.

Due to this, Benitez would be traded less than a month later and it ended up being a waste of assets for him.

12 Signing Jacoby Ellsbury

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Jacoby Ellsbury was an absolute superstar with the Boston Red Sox and led them to two World Series. However, when he became a free agent in 2013, he became this era’s Johnny Damon and signed with the Yankees. The deal ended up being a 7-year, $153 million contract.

The contract was met with some praise because Ellsbury had become a five-tool player over the years. However, his tenure with the Yankees has been absolutely abysmal thus far and now he is their fourth outfielder. That is a plethora of money for a bench player and it definitely is one of their worst moves of this era.

11 Jeff Weaver Trade

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Jeff Weaver had an abundance of potential when he was traded to the Yankees during the 2002 season and was expected to grow into a star there. However, this quickly would turn out to be false, as Weaver would struggle immensely and eventually even was delegated to the bullpen.

Besides the fact that Weaver was just awful with the Yankees, it is important to note that they gave up star pitcher Ted Lilly in the move. Lilly would go on to have a spectacular career, while Weaver would be horrible for the Bronx Bombers. Overall, this was a horrible decision in its entirety.

10 Nick Johnson’s Second Stint

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Nick Johnson was once one of the top prospects for the New York Yankees when he first entered their system. However, Johnson ended up being traded just two seasons after his debut to the Montreal Expos for Javier Vazquez. There would be a bit of regret from this trade, as Vazquez did not work well in New York.

However, in 2009, the Yankees brought back Johnson in 2010 and expected him to be their DH. Yet, Johnson’s return to New York did not work out at all, as he was constantly injured. His stats also fell off dramatically and he was far below the league average in most categories during his limited play time.

9 The Esteban Loaiza Trade

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It is hard to believe that the Yankees got worse in the Jose Contreras deal, but they made it somehow happen. The Yankees, at the time, thought they stole Esteban Loaiza from the White Sox. Loaiza had just won the Cy Young Award and looked absolutely dominant the year before.

With the Yankees, Loaiza was absolutely horrid and even lost his spot in the rotation shortly after.

He was expected to be their potential ace, but was one of the worst pitchers in the entire league his lone season with them. With that being said, he would end up being traded out of New York shortly after.

8 Trading Away Tyler Clippard

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Tyler Clippard was once a top notch prospect of the Yankees and seen as a big part of their future. He would end up pitching only one season with the Yankees before he was shockingly traded away to the Washington Nationals. This would be another move that would come with regret.

After moving to the bullpen, Clippard became one of the best relief pitchers in the entire MLB. In fact, Clippard would end up making two all-star games with the Nationals. The Yankees definitely could have used Clippard because he easily could have been their replacement closer when Mariano Rivera retired.

7 Bringing Back Kevin Brown

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Kevin Brown was a spectacular pitcher during his prime years in the MLB and had an abundance of success. So when the Yankees traded for him in 2004, it looked as though that it would end up being a wonderful move for them. He was an all-star and one of the best pitchers in the league.

However, age finally caught up to Brown and was absolutely horrible when the season meant the most. After punching a wall and breaking his hand, Brown was abysmal in his return during the playoffs against the Red Sox. This of course played a huge factor in their 3-0 blown lead and loss in the series.

6 Signing Jaret Wright

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During the 2005 off-season, the New York Yankees signed Jaret Wright to a three-year,$21 million deal. The Yankees had hope that he would provide them with solid depth in their rotation, as he had just come off his best season ever with the Atlanta Braves. This was initially seen as a steal of a signing.

However, Wright quickly came back down to Earth with the Yankees and pitched like he did throughout the entirety of his career beforehand. In his two seasons with the Yankees, his ERA would never leave the upper 4.00 and hit as high as the 6’s. This would end up being a waste of a signing and he would end his career in Baltimore.

5 The Lance Berkman Trade

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Lance Berkman was a real star with the Houston Astros and it made sense that the Yankees wanted him. However, as a rental for the Yankees, he struggled immensely and looked like a shell of his former self.

He would end up only hitting one home run in 37 games and failed to be the offensive machine they had hoped.

The hardest part about this trade for the Yankees is that they traded away relief pitcher Mark Melancon. Melancon was a top notch prospect in their system and reached his potential as his career progressed. He has been a three-time all-star and definitely an arm the Yankees wish they kept.

4 Signing A.J. Burnett

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The New York Yankees were very active during the 2006 off-season and made this clear when they signed A.J. Burnett to a whopping five-year, $82.5 million dollar deal. This came after Burnett became a very solid starter with the Toronto Blue Jays. The Yankees expected him to become their second starter.

However, his stint with the Yankees ended up being a failure overall, as he failed to reach expectations entirely. With the Yankees, his ERA was continued to get higher and he had two seasons with it in the 5’s. Burnett simply could not handle the pressure of playing in the Bronx and his stats suffered immensely.

3 Signing Kei Igawa

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Kei Igawa was expected to be an absolute star when the New York Yankees signed him to a five-year, $20 million dollar contract in 2006. It is important to note that the Yankees also had to pay $26 million extra for his rights from Japan. Needless to say, they had a lot of hope for him and saw him as their future ace.

However, Igawa was a mega bust with the Yankees as soon as he arrived. Igawa would only play parts of two seasons with the Yankees and struggled immensely in the process. He soon found himself only two winters after signing this massive deal. This contract was definitely of their worst mistakes.

2 Javier Vazquez’s Tenures

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Javier Vazquez was a very reliable starter basically everywhere he pitched during his career, besides with the New York Yankees. As previously stated, the Yankees lost Nick Johnson’s prime years with the first Vazquez trade and in return, got mediocre pitching for one lone season out of Vazquez.

However, the Yankees gave Vazquez a second chance in 2010 and gave up players such as Melky Cabrera and Arodys Vizcaino. Vazquez was coming off a spectacular season with the Braves that year, so the trade made sense. Yet, Vazquez was awful again with the Yankees and let go the next season yet again.

1 Signing Carl Pavano

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The Yankees thought they were lucky when Carl Pavano signed a bargain deal with them, instead of other teams who offered more money. However, the deal was still hefty, as it was a four-year contract worth $39.95 million. Pavano had a marvelous season the year before with the Marlins, so the signing was met with praise.

However, Pavano was the worst signing of the 2000s by the Yankees.

After starting off well, he kept getting continuously injured, including keeping one secret about being in a motorcycle accident. He sat out the entire 2006 season and his teammates questioned his desire to pitch. Pavano struggled for the rest of his tenure in New York and eventually was just given up on.

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