MLB Free Agency: Ranking the 10 Worst Signings for the Yankees in Recent History

With the World Series currently going on, it means that the 2011 baseball season is almost over.

Which means free agency and the winter offseason is upon us.

We all know the Yankees have been one of the most active teams when it comes to making changes to their team, especially in free agency.

The Yankees make more money than any other team in baseball, and put that money back onto the field by providing the fans with top talent.

Some of that talent over the years has been really good.

And some of it, has blown up in the Yankees faces.

This list is going to see what free agent deals the Yankees and GM Brian Cashman should have never made.

Honorable Mention: Richie Sexson

Sexson may go down as one of the worst free agent signings for the Seattle Mariners with a four-year, $50 million deal.

In fact, Sexson was so bad for Seattle, they released him on July 10, 2008, in the final year of his deal and just ate the rest of the contract.

To try and bolster their offense and the bench, the Yankees signed Sexson on July 18, 2008.

He hit .250 with one home run and six RBI with the Yankees in just 22 games.

Clearly, Sexson was hardly the bat-and-player he was with Milwaukee and Arizona who hit 40 home runs.

Sexson was designated for assignment by the Yankees on August 15. On August 24, the Yankees released him.

He drew no other interest from any team in baseball and shorty retired after that at age 33.

10. Kyle Farnsworth

The current closer of the Rays was once the setup man for Mariano Rivera and the Yankees.

The Yankees gave Farnsworth a three-year, $17 million deal to replace Tom Gordon in the bullpen. Farnsworth struggled for the Yankees though in the two and a half seasons in New York.

In 2006, he went 3-6 with a 4.36 ERA in 72 appearances.

In 2007, he went 2-1 with a 4.80 ERA in 64 appearances.

In 2008, Farnsworth was reported to be on the trading block and was 1-2 with a 3.65 ERA before being traded on July 30, 2008 to the Tigers for catcher Ivan Rodriguez.

Farnsworth never really lived up to the hype as a dominant reliever for the Yankees and trading him was best for both sides.

9. Kenny Lofton

Before he got to the Yankees, Kenny Lofton was a great player.

With the Indians and Braves, Lofton was one of the best lead-off hitters in baseball with great speed and excellent defensive skills.

The Yankees signed him before the 2004 season to compete with Bernie Williams for the center field job.

But age 37, it was clear that Lofton was not the player the Yankees expected.

In just 83 games, Lofton hit .275 with three home runs, 18 RBI and seven steals.

Lofton didn't like how he was used in New York and never really got along with Joe Torre.

So to accommodate the unhappy outfielder after the season, the Yankees shipped Lofton off to the Phillies for reliever Felix Rodriguez.

8. Jose Contreras

Before the 2003 year, Contreras defected from Cuba and signed a four-year, $32 million deal with the Yankees.

Contreras actually had decent numbers, but he benefited from run support.

In 2003, he went 7-2 with a 3.30 ERA in 18 games, nine of which were starts. He spent a lot of time on the disabled list in 2003 and some in the bullpen.

In 2004, he went 8-5 with a 5.64 ERA in 18 starts before he was traded to the White Sox for Esteban Loaiza, who was even worse.

Contreras went on to pitch and win in the 2005 World Series for the White Sox.

But as a Yankee, Contreras never lived up to the hype coming over from Cuba.

7. Hideki Irabu

Irabu was almost a pitcher for the San Diego Padres.

The Padres purchased the contract of Irabu from the Chiba Lotte Mariners Japanese baseball team, but Irabu refused to pitch for the Padres and only wanted to go to the Yankees.

So for the negotiating rights for Irabu, the Padres got Ruben Rivera, Rafael Medina and $3 million in cash.

The Yankees then signed Irabu to a four-year, $12.8 million deal before the 1997 season.

In 1997, Irabu went 5-4 with a 7.09 ERA.

In 1998, Irabu went 13-9 with a 4.06 ERA.

In 1999, Irabu went 11-7 with a 4.84 ERA.

Because of Irabu's heavier weight, it lead George Steinbrenner to publicly call Irabu a "fat, pussy toad" before a spring training game after Irabu failed to cover first base.

After the 1999 season, Irabu was traded to the Montreal Expos for minor leaguers Ted Lilly, Jake Westbrook and Christian Parker.

Irabu never lived up to the hype from coming over from Japan and retired from baseball after the 2002 season.

Irabu committed suicide on July 27, 2011. He was only 42 years old.

6 Jaret Wright

When Jaret Wright emerged onto the baseball scene in 1997, he was seen as a can't miss arm for the Indians.

He pitched very well for them as a 21-year old rookie in the playoffs, including starting Game 7 of the World Series.

But Wright ran into arm and shoulder problems and had to have Tommy John Surgery in 2003.

He resurrected his career in 2004 with the Atlanta Braves, posting a 15-8 record and entered free agency.

With a major need for pitching, the Yankees signed Wright to a three-year, $21 million deal before the 2005 season.

In 2005, Wright went 5-5 with a 6.08 ERA in 13 starts and spent most of the time on the disabled list.

In 2006, Wright went 11-7 with a 4.49 ERA in 28 starts.

He started Game 4 of the ALDS against the Tigers and got shelled in the loss.

After the season, the Yankees shipped Wright off to the Orioles for reliever Chris Britton.

The Yankees should have never of signed Wright after the 2004 season.

5. Sidney Ponson

Once upon a time, Sidney Ponson was a pretty good starting pitcher for the Orioles.

The Yankees had him twice, and he wasn't very good for them either time.

The Yankees first signed him on July 14, 2006 to try and help the rotation.

He went 0-1 with a 10.47 ERA in three starts before being sent to the bullpen.

He was later released on August 18, 2006.

In the 2008 season, the Texas Rangers released Ponson after he blew up at the Rangers, manager Ron Washington and GM Jon Daniels.

The Yankees, who were in desperate need of pitching after they lost Chien-Ming Wang for the season, re-signed Ponson on June 9, 2008.

Ponson went 4-4 with a 5.85 ERA in 15 starts.

The Yankees didn't make the postseason in 2008, the first time since 1993. (1994 doesn't count because baseball went on strike.)

In both stints, Ponson was terrible for the Yankees.

4. Josh Phelps

Some of you might be wondering who in the heck is Josh Phelps?

He might be the one reason why Bernie Williams didn't get a roster spot for 2007.

Yes, the Yankees brought in Phelps and long-time first basemen Doug Mientkiewicz to compete for roster spots, while the Yankees didn't even offer Bernie a major league contract.

Mientkiewicz I agreed with, because he had a great glove and could have been very useful.

But Phelps, I was against 100 percent, even when he was killing the ball in spring training, I was against this guy taking Bernie's spot on the roster.

In 36 games, he hit .263 with two home runs and 12 RBI before the Yankees designated him for assignment on June 19, 2007.

We gave this guy a roster spot over Bernie Williams? Shame on you Cashman.

That's why Phelps ranks so high on this list.

3. Tony Womack

In all fairness to Brian Cashman, he did not take part in the Yankees signing Tony Womack.

Nope, this was all part of the Yankees front office going over Cashman's head and making moves without his say-so.

The Yankees and Miguel Cairo couldn't reach a deal, so the Yankees signed Womack to a two-year, $4 million deal on December 8, 2004, to be their starting second basemen.

Womack was a product of the National League and was a good lead-off hitter and base stealer.

With the Yankees, he was dreadful. In 108 games, Womack hit .249 with no home runs, 15 RBI and 27 steals. In the field, he was a disaster, making 15 errors.

He was so bad, Joe Torre moved Womack to left field and lead to Robinson Cano getting called up in May of 2005.

In the outfield, Womack was no better either and became a regular part of the bench. After the 2005 season, Womack was traded to the Reds for two minor leaguers.

This was one of the signings that nearly had Cashman leave the Yankees after the 2005 season.

2. Carl Pavano

I have a special place for Pavano in my heart...filled with utter hatred.

Before the 2005 season, Pavano was one of the top free agents on the market after pitching well for the Florida Marlins, helping them win the World Series in 2003.

The Red Sox, Orioles and Reds all wanted him, but in the end, the Yankees ended up winning the services for Pavano with a four-year, $39.95 million deal.

In 2005, Pavano was 4-6 with a 4.77 ERA in 17 starts before being put on the disabled list with an injured right shoulder.

We didn't see Pavano pitch again until 2007, because in 2006, Pavano injured his buttocks in spring training, and also broke two ribs in August of 2006 in a car accident, he failed to tell the Yankees of the incident until the day after it happened.

What made the Yankees so upset is that they were planning to activate Pavano off the DL and couldn't because of the wreck.

In 2007, Pavano made two starts before finding out he had damage in his elbow, which required Tommy John Surgery, ending Pavano's 2007 season.

Pavano finally came off the DL on August 23, 2008 for the Yankees and ended the 2008 season with a 4-2 record and a 5.77 ERA.

The only reason Pavano came off the DL was so that he could get another free agent contract in 2009.

In four years with the Yankees, Pavano went 9-8 with a 5.00 ERA in 26 starts.

"The American Idle" proved that he was in fact, a $40 million-dollar waste of money and space.

1. Kei Igawa

Brian Cashman, what were you thinking?

OK, so the Yankees really wanted Daisuke Matsuzaka, who ended up going to the Boston Red Sox, who bid the most for his services.

So after missing out on Matsuzaka, the Yankees turn around and bid the most for Igawa and were the highest bidder, which was announced on November 29, 2006.

The bid to negotiate for Igawa was $26 million, which went to the Hanshin Tigers of the Japanese baseball league.

The Yankees then gave Igawa a five-year, $20 million deal on December 27, 2006 and was put into the rotation for the 2007 season.

Igawa was down-right awful pitching for the Yankees. In 2007, Igawa went 2-3 with a 6.25 ERA in 14 appearances.

He was sent down to the minors in May because of flaws in his mechanics and was recalled on June 22.

He got sent back down to the minors on July 27.

In 2008, he made two appearances one only one start for the Yankees, going 0-1 with a 13.50 ERA.

Since then, Igawa has been nothing more than a minor-league pitcher for the Yankees, and he will be relieved of his contractual obligations with the Yankees after the 2011 season.

Igawa goes down as the worst free agent contract in recent history for the Yankees.