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While Jobu is on vacation, enjoy one of our greatest hits as Clu shows you just how badly the Yankees messed up in free agency.

I have been on a mission over the past few weeks or so: coming up with a list… A list of infamous players who donned the pinstripes for boat loads of money, courtesy of the late George Steinbrenner, and absolutely bombed playing for the bombers (see what I did there?). After endless nights of searching and debating, I’ve come up with a list of players who were fitting for this list…so I present to you the worst Free Agent signings in the recent memory of the New York Yankees.

Hideki Irabu – Starting Pitcher (1997-1999)

This may have been Irabu’s crowning achievement in pinstripes. (Reuters)

The first Hideki… Many people remember him from the comment George Steinbrenner made, publicly calling him a “Fat Pussy toad” (not making that up) when Irabu failed to cover first during a spring training game. Irabu was deemed out of shape, and Steiny wanted nothing to do with that. Irabu was never the player that everyone thought he would be when he was a star in Japan. He retired after five short seasons in the bigs, and committed suicide on July 27th, 2011 at the age of 42.

Jason Giambi – 1B/DH (2002-2008)

Not even a killer mustache could keep Giambi off this list. (Uli Seit/New York Times)

Now, hear me out people!! I want to explain something before you start coming at me with pitch forks and torches! The reason I put Giambi on this list is simple… Despite his 7 year, $120 million deal, he only produced MVP numbers for one season. That was in 2002, when he hit 41 home runs and batted over .300. I put him on this list because of his superb fielding ability, how much he liked to sweat, and of course, who can forget that one year in 2008 when he was hitting .109 through April 20th… .109!!! I mean he did manage to raise his average to a meaty .164 by the end of the month but that’s really the reason why he’s here. No one who gets a $120 million dollar contract should ever be putting up those numbers. And by the way, is it just me or did he always seem to be plagued with some sort of bizarre injury like when he hurt his foot rounding the bases and got plantar faschiatis? Or how about that parasite infection he had? Probably just a bad food truck in the Bronx.

Tony Womack – 2B/OF (2005)

Truly a team hero, because he sucked enough to lose the job to Cano. (Donruss)

Right off the bat, I will say that this particular signing almost caused Yankees GM Brian Cashman to leave following the 2005 season. It wasn’t so much the dollar amount he was signed for, as the Yanks only gave him a 2 year/$4 million dollar contract. He was signed with the idea that he was a solid leadoff guy, could steal bases and flash the leather in the field. Well, none of that happened. Even though he did manage to have 27 stolen bases, his .249 avg and 15 errors cost him the leadoff spot, then his job at second base. Shortly after that, he was given a nice kick-in-the-ass trade to the Reds (following the 2005 season), as Manager Joe Torre much favored the young second baseman Robinson Cano. The rest is history. So in a way….thanks Tony Womack! Sit back and have a cold one, because we now have one of the best hitting and fielding second basemen in the league, and we have you to thank for it!!

Kyle Farnsworth – Relief Pitcher (2006-2008)

He can’t see or pitch without his glasses! (Jamie Squire/Getty Images)

Yankees signed Farnsy to a 3 year, $17 million dollar contract in 2006, basically based on his 2005 season when he went 1-1 with a 2.19 era, 1.01 WHIP, and 16 saves. He was chosen to become the new setup man to Mariano Rivera and, in his first season, he didn’t exactly have setup material, as he put up a 3-6 record and a 4.36 ERA. Eventually the Yankees traded him for Catcher Ivan Rodriguez when they realized “Farnsy” wasn’t ever coming around. Since then he has pitched for Kansas City, Atlanta, and was even the closer for the Tampa Bay Rays in 2011.

Jaret Wright – Starting Pitcher (2005-2006)

You can tell a lot about Wright’s Yankees tenure by the look on everyone’s face here. (Unknown)

Coming off of the 2004 season, the Yankees were in dire need of pitching. So, with a little extra money in his pocket, Steinbrenner went out and signed Jaret Wright to a 3 year, $21 Million dollar a year contract. Wright, who just so happened to resurrect his career the year before in Atlanta (15-8 record & a 3.28 ERA in ’04), sucked it all up, even on the field too. He earned his cool $7 Million in 2005 with a 5-5 record and a sparkling 6.08 ERA. 2006 turned out to be slightly better, as he had a winning record but still struggled with a high ERA. Hey though, he did start game four of the ALDS, where he was destroyed by Detroit. He was banished to play on the Orioles after the 2006 season in a trade for Zach Britton, good riddance!

Kei Igawa – Starting Pitcher (2007-2011)

He’s gonna throw the ball so hard… you’ll see. (

Now I was debating putting Igawa at the #1 spot but, after doing some research, he actually was the lesser of two terrible players. Igawa came over for Japan after pitching for the Hanshin Tigers of the Nippon Professional Baseball league. From 1999-2006, he was one of the biggest superstars for the Tigers. He led the league in strikeouts in 2003, won the Eiji Sawamura Award (Japan’s Cy Young) and was also the Central League MVP. In 2004 he led the league in strikeouts with 228. After the 2006 season he announced his intentions on playing in the Majors, so the Yankees went all in and placed a $26,000,194 bid for his services (he 194 being for the strikeout total that he had in 2006). This ploy was all because the Yanks had just lost out on another Japanese pitcher, Daisuke Matsuzaka who got a winning bid from the Boston Red Sox that was worth $51,111,111.

After the bid, the Yankees signed Igawa to a 5 year, $20 million dollar contract. Igawa got his first start on April 7th, 2007 and he was smacked around by the Orioles, but ended up with a no-decision thanks to a tremendous walk-off grand slam by Alex Rodriguez. He was immediately sent down when they noticed problems with his mechanics and location and he would spend the next three seasons in and out of the majors. Eventually, he became a main stay for the Scanton/Wilkes-Barre Yankees. The one accomplishment Igawa had during his time with the Yankees was that he set the SWB Yankees’ franchise record for wins with 31. He’s a hero if you ask me. Igawa stayed with the Yankees organization until his contract expired and in 2012 and then signed a deal with the Orix Buffaloes back in Japan

And the worst signing in Yankees history goes to….

Carl Pavano – Starting Pitcher (2005-2008)

“American Idle” walked off with the trainer… a lot. (Reuters)

Ahh the notorious Carl Pavano. What can I say about him that Yankee fans already don’t know? Nothing!!!! After helping the Florida Marlins to a World Series championship in 2003 (against the Yankees none the less), he became a very high profile free agent following the 2004 season. The Boston Red Sox, Baltimore Orioles and Cincinnati Reds all wanted his services and offered him boatloads of cash, but in the end he decided to go to the Yankees for a 4 year, $39.95 million dollar deal. Not bad for someone we thought was to be a #2 starter… Ohhh boy did those other teams dodge a bullet.

In the four years Pavano was on the Yankees, he compiled a 9-8 record and a 5.00 ERA in 26 appearances. He would completely miss the 2006 season because of injuries to the following body parts: his elbow (would have Tommy John surgery), shoulder, buttocks (don’t ask how), and two ribs (after a car accident two days before he was scheduled to come off the DL in ’07). He was scorned by every Yankee fan, the staff and even teammate Mike Mussina. He was even dubbed “American Idle” by many (even by this guy, Pavano’s biggest fan).

The Yanks did manage to salvage something out of him in 2008, when he was basically playing for his next contract, posting a 4-2 record and a 5.77 ERA. And, after doing some research, I figured out that the nine wins he had earned in those four years were worth approximately $4.4 Million each. Totally worth it! Once he was run out of town, he signed a one year deal with the Indians, then was traded to the Twins, where he currently still plays.

Featured image courtesy of: Corbis Images

About Big League Clu

Clu Haywood leads the league in most offensive categories, including nose hair. When he sneezes, he looks like a party favor. Also, he's been known to hit the ball "too high" and alleges to have illegitimately fathered Jake Tayor's non-existent children. You can also find him on Twitter @bigleagueclu