Top 5 Worst Yankees Free Agent Pitchers of All Time

What recession? By dumping a behemoth-sized pile of cash in front of C.C. to sway him back to the East, the Yankees simply did what they had to do. Yes, the contract is huge, and Sabathia’s waistline is huge, but if he brings October glory into the new stadium, none of that will matter.

Now that we have a legitimate ace on the staff, the prospect of Opening Day 2009 grows even more exciting. To appreciate just how important of an accomplishment this is for Brian Cashman and the boys, let’s take a look back at some of the all-out misfires the Yankees have made in the not-too-distant past while testing the free agent waters for starting pitching.

Warning: Some of the following names may induce severe bouts of rage and/or depression for the average Yankees fan. Please proceed with caution.

5. Kenny Rogers (1996). “The Gambler” spent just two seasons in the Bronx before being traded to Oakland for the infamous “player to be named later,” and never quite lived up to the buzz that stemmed from tossing a perfect game for the Rangers in 1994. Sure, the Yankees won their first World Series in 18 years during Rogers’ first season in pinstripes, but this was no thanks to Kenny, who never reached later than the third inning of any of his postseason starts that year. As everyone in Yankeeland knows, October futility will get you shipped out of town faster than Julia Roberts’ run on Broadway (unless you make $25 million a year and have fabulous highlights in your hair).

Since leaving the Yankees, Rogers showed why he doesn’t belong on America’s Team by doing his best Sean Penn/Randy Johnson impersonation and attacking an on-field cameraman during a pre-game warm-up in 2005. A silver lining in this failed acquisition? That “player to be named later” from Oakland turned out to be 1998 World Series MVP Scott Brosius. Thanks, Kenny.

4. Jaret Wright (2004). Did Brian Cashman bump his head and think he was back in 1997 when he pursued Wright to help bolster the Yankees rotation four years ago? Long gone was the cocky Cleveland Indian fireballer who flustered the Bronx Bombers in his first ever postseason appearance (’97 ALDS). Instead, Yankees fans were treated to a fifth starter who took the phrase “laboring on the mound” to a brand new level. With one eye glued to the scoreboard at the old stadium you would almost, almost, feel bad for the guy as the number on the Duane Reade pitch-counter climbed into the 40s and even 50s in just the second inning.

Watching Jaret Wright trying to retire the side was like watching Jimmy Fallon attempting to make it through a sketch on Saturday Night Live without smirking or even cracking up altogether. They would both make you shudder with disgust.

So, where is this mistake of an acquisition now? After failing to make the pitching-challenged Pittsburgh Pirates squad last spring, Wright is looking for work and wondering why Cashman won’t return his phone calls anymore.

3. Jose Contreras (2003). After a bidding war with the rival Red Sox to acquire the services of Cuban defector Contreras, the Yankees were hoping they had scooped up another Orlando “El Duque” Hernandez, a crafty professional who would slide seamlessly into an already stout starting rotation of Clemens, Pettitte, Mussina and Wells. Well, let’s just say that didn’t exactly happen. Contreras showed flashes of capability, but never really felt comfortable performing under the bright lights of Broadway.

The big righty’s worst moment in pinstripes came in pivotal Game 5 of the 2003 World Series against the Marlins. When starter David Wells went down with an injury after just one inning, Contreras came on in “relief” to promptly get rocked for three quick runs in the second, setting the tone for the rest of the game.

The biggest burn of the Contreras signing? After giving up on the overpriced hurler, the Yankees traded him along with cash to the White Sox during the 2004 season, only receiving (gulp) Esteban Loaiza in return. Contreras found a rebirth in Chicago and went on to help the Sox win the World Series in 2005. We don’t need to mention how the Yankees have fared since then.

2. Kei Igawa (2007). Oh no, the Red Sox just forked over big bucks to sign a Japanese pitcher, now we have to get one too. Such was the thinking when the Yankees shelled out $26 million just to talk to Igawa about signing a 4-year, $20 million contract. Add everything up and you get . . . the highest paid Triple-A pitcher in the history of baseball.

Is there anything more to say about this one? Someone, anyone, please just take him away!

1. Carl Pavano (2004). Who else could claim the top spot but Mr. “American Idle” Pavano himself? No-brainer. Hey, this guy had his own MRI wing named after him at the Yankees’ training facilities in Tampa. Let’s do the rundown: bad shoulder, balky back, bone chip in the elbow and even a strained buttocks (come on, that just sounds made up). All of these obstacles kept Pavano from toeing the rubber during his 4-year tenure in the Bronx. And if that wasn’t enough, who can forget the time the righty broke two ribs after spinning his Porsche into a parked truck, then failed to report the accident to either the police or anyone from the Yankees organization? There has to be something more to this story that we don’t know about. Like, was Amy Winehouse riding shotgun or something?

No one could blame Cashman and The Boss for throwing money at Pavano—he was the most sought-after free agent starter on the market at the end of the 2004 season, not to mention a Yankee-stopper in the 2003 World Series while pitching for the Marlins—but seriously, how could this one have turned out any worse? Pavano jumps out of the bullpen and picks a fistfight with one of the right field Bleacher Creatures?

Now that it’s all said and done, and Pavano’s stint with the Yankees has mercifully drawn to a close, the final numbers speak for themselves on what a colossal bust this signing turned out to be: 4 years, 26 games started, 9-8, 5.00 ERA. When the dust settles, Carl walks away from all of this with a cool $39.95 million in his pocket. That equates to roughly $1.54 million per start. A few more financial debacles like this one, and the Yankees may be next in line for a federal bailout.

No, I didn't miss the end of the season . . .

Check out how I wrapped up the Yankees' dismal last season at the old stadium with some severe blogging on the Armchair Sports Authority website:

We All Deserve Better Than This

Too Little, Too Late?

The Yankees vs. 90210

Sayonara, Yankee Stadium

Jeter Epilogue . . . .

Hopefully anyone watching the Yankees' sorely needed 5-3 win over the Rangers last night recognized one crucial element that led directly to the victory, and that was the clutch hitting performance of one Derek Jeter. Seeing the Captain go 2-4 with 2 RBI—driving in the go-ahead run in the third, then an important insurance run in the fifth—made one thing abundantly clear to me: Jeter obviously read my blog yesterday and decided it was time to step up and carry this slumping team.

Is it a coincidence that mere hours after I call him out, Jeter responds with two big hits to put the Yankees over the edge? Hardly. His run-scoring double deep to the gap in right center was vintage Jeter, something I've been longing to see for most of this season.

So, now I understand the magnitude of my blogging powers, no matter how painful they may be to write (I still love you, Derek. You just needed to hear the truth, now you can get back on track. I promise I'll come down and work out at your new 24 Hour Fitness gym on 26th st. Hmmm, maybe I should edit that last sentence. . . .).

And now I will direct this power at the next weekly Yankee goat, this time it's none other than A-Rod. Maybe the 3-time MVP is taking this "trying to be like Derek" thing a little too far, because he's hitless in the Rangers series so far, including knocking into a "Jeter-esque" three double plays in the last two games.

Come on, A-Rod. This is the stadium where you spent three years putting up Playstation-like numbers. You can't manage one hit? Just one? The Yankees have enough problems right now (I'm still in denial about most of them. Joba on the DL? I can't take it!) to deal with your ice-cold bat. I don't care if you need to listen to Papa Don't Preach, or better yet, Into The Groove, on your iPod before every at-bat. Whatever it takes, just get it done!

Now, let's see how much power this little blog actually wields. . . .

Where have you gone, Captain Clutch?

I can't believe that I'm about to do this, but someone has to speak up and admit what has become painfully obvious: Yankee Captain Derek Jeter, at least up to this point in the season, has lost his edge (No pun intended, although if I see one more of Jeter's Ford Edge commercials I might throw my television out the window). This might sound like first class Yankee sacrilege, but just hear me out. I'm not accusing the guy of not going hard after ground balls, or dogging it down the first base line. Those kinds of things certainly more aptly fit the profile of an aging star who gets cranky and forces a trade with the Dodgers. That's not Jeter.

But let's not pretend not to see what's been happening all season long: Derek Jeter has been one of the biggest underachievers in a staggeringly pedestrian Yankee lineup (ninth in the MLB in total runs scored) that was supposed to threaten the single season team scoring record this year . . . . There, I've said it (taking a deep breath). I didn't know if I could get that out, but it's done. Let's move along.

Jeter is currently batting a career-low .279, well below his career average of .315, but his lack of production goes beyond the numbers. It's been the Captain's failure to deliver in big situations (something he's always had a knack for in his illustrious career) this season that should disturb Yankees fans across the country. Look no further than last night's 8-6 loss to the Texas Rangers, the latest of the team's crushing defeats, for examples of Jeter's newfound slippage from hero to rally-killer. 

In the top of the third inning the Yankees trailed 3-0, but were set up with runners on first and second with one out. Jeter strolls to the plate with a chance to get back his team back into the game. Here we go, right? Wrong. Routine grounder to third for a tailor-made, inning-ending double play (Jeter now ranks second in the league with 18 twin-killings. 18!). Threat over. The top of the seventh gave Jeter another chance: bases loaded, two outs, Yanks down 5-2. A few years ago Captain Clutch would have knocked a single to right center with his patented inside-out swing and drove in two runs. This year's Jeter? A weak liner right to the second baseman.

Maybe I'm being too hard on Jeter. Perhaps Yankees fans have grown so accustomed to watching him always fueling an important rally or making the big defensive play in a tight game, that we expect it from him every single at-bat of every single game. That's not fair to any player, even Derek Sanderson Jeter. But we get confused when he see him fail. It just doesn't seem right. Where's the World Series walk-off home run? Where's the impossible "flip play" to catch the runner at home? Where's the crashing into the front row of the box seats to catch a foul ball in a close game against the hated Red Sox?

At 34, Jeter is obviously on the down slope of his career, but here's hoping he still has enough left in the tank to give us something to cheer about. It's not easy to watch our heroes slide from the top of the world into mediocrity, or sometimes even lower. I still cry when I think about Chevy Chase's collapse from thriving in comedic gems like Caddyshack and Fletch to almost complete oblivion. Anyone seen him lately? Scary.

Thankfully Jeter is not Chevy Chase. He'll remain relevant in the world of sports, entertainment, and commercial marketing as long as he likes. But it would be a shame to think that the only highlights left in Jeter's career include operating the sunroof on his Ford Edge, hitting line drives into a supermarket display of Gillette Fusion razors, or chumming around with tools like Tiger Woods and Roger Federer in the locker room.

I want my money back

"I'm hoping this is rock bottom." These words offered from first-year manager Joe Girardi after last night's 12-2 drubbing by the Orioles, the latest of colossal disasters to take place this season at the old stadium, perhaps most accurately describe the sentiments of Yankees fans across the universe today. The trouble is, it's unwise to assume the team has indeed reached rock bottom, because as the past week has taught us, it can get worse. You never know just how ugly things can get until the next game rolls around to remind you.

With the raindrops threatening to mercifully postpone the game last night, my friend and I arrived at Yankee Stadium a few minutes late. The rest of the tardy fans seemed to be buzzing about the return of A-Rod, fresh off the DL to rescue the floundering offense. We were excited that the weather had decided to cooperate. Maybe this was a sign of things turning around. The Subway Series, as dismal as the afternoon skies had been, was behind us. It was time to start fresh with a new series against Baltimore. Things were looking up. They had to be. We felt hopeful as we made our way through the turnstyles and into the gate. . .

This feeling vanished before we even made it to our seats.

John Sterling's voice on the overhead radio inside the stadium announced that Baltimore had just scored on an RBI triple. Great, I thought. We're already giving up runs in the first inning. It's okay, it's just a run. Let's just get to our seats and find the beer guy. But then I glanced up at one of the refreshment counter televisions showing the game. My friend had to confirm what my eyes were reading. 7-0 Baltimore.

The momentum leading us to the upper level escalator escaped from our bodies faster than a Melky Cabrera at-bat (I was going to use Cano for this metaphor, but I've probably picked on him enough in the past). What to do? After a half dozen phone calls about whether or not we should risk the rain and head to the stadium, this is what we're greeted with?

Eventually we did reach our seats. By that time all I could really do was laugh. Someone forgot to tell me we were going to a Ravens/Giants game. It seemed the Ravens had returned the opening kickoff for a quick touchdown.

But the laughter didn't stop here. Watching Johnny Damon trying to catch a routine fly ball that would have ended the top of the second inning, but instead allowed in two more unearned runs, made me feel sorry for Bobby Abreu being upstaged by his teammate. Unbelievable.

By the fourth inning we had squatted comfortably in our Loge seats on the third baseline. We sipped beer and ate cold pretzels (that's a whole new complaint I'll address in the future), and talked about different important crossroads in both of our lives, vaguely aware of the football, er, baseball game taking place in the background.

When A-Rod connected for a long two-run homer (a safety by the Giants) in the sixth to put the Yankees on the scoreboard, we didn't know what to do. We tried to get excited, but it didn't feel right. It was like being the only two white guys at the Apollo during a Public Enemy concert, and the crowd goes wild as Chuck D reads a Malcolm X quote. We kind of gave each other an uneasy look and shrugged. What do we do? It's hard to stand up and cheer during an eight-run Yankee deficit.

Is this rock bottom? I'm afraid to ask.

Déjà vu all over again . . . and again.

Nothing like squaring off against your crosstown rivals to . . . send an already slumping team even deeper into the doldrums of gross underachievement. Wow, what a terrible baseball team. There's no clever way of paraphrasing things, so I won't even bother trying. The Yankees are just plain awful right now.

How awful? One fact should sum things up nicely: the Bronx "Bombers" managed to scratch out just three hits on Sunday against erratic lefty Oliver Perez. Oh, by the way, they also got crushed 11-2 in humiliating fashion by an equally underachieving Mets squad who came into the latest Subway Series having just dropped three of four to the lowly Nationals. That awful.

So, here we go again. For three seasons now, the Yankees have stumbled out of the gate, raising serious questions about the team's ability to continue their historic run of reaching the playoffs every year since the strike-shortened 1994 season. Will this be the year they finally bury themselves in too deep of a hole to climb back out of?

Time will tell, but here's what we do know about the 2008 New York Yankees: this lineup is growing more and more unwatchable by the day. 12 runs in their last six games? Are you serious? Right now this lack of run production is an even bigger problem than the suspect pitching because the former compounds the latter. Every starter that takes the mound feels he has to be near-perfect if he wants any chance at getting a win, putting more and more pressure on every single pitch.

Here's a simple formula for shutting down this offensive Yankee offense: 1) Put the first two batters of every inning on base. 2) Watch as the ensuing batters find new ways to not drive in runs (this can take place in a variety of sequences, e.g. strikeouts, popouts, or the always exciting inning-ending double play). 3) Walk calmly back into the dugout and prepare to repeat this process in the following inning.

In 44 games this year the Yankees are batting a sickly .238 (11th in the American League) and have scored 123 runs (dead last in the AL) with runners in scoring position. That pretty much says it all. Gone is the trademark Yankee patience at the plate that so effectively used to drive up pitch counts and yield bases on balls, although those batters who happen to work a walk very rarely reach home plate these days. 

Remember when Johnny Damon used to wear out pitchers with epic at-bats featuring a slew of foul balls before finally either slapping a base hit to left field or seeing ball four? Yeah, well, that's been replaced by a leadoff hitter hacking and trying to knock everything out of the ballpark, thinking that with A-Rod on the DL someone has to make up for the missing power.

Bobby Abreu, another veteran hitter known for his patience at the plate, has apparently become too patient, as he has grown a penchant for ringing up backwards K's with runners on base, all the while flashing his patented "I'm-completely-indifferent-about-this-at-bat-what-time-are-we-meeting-at-Le-Cirque-for-dinner-after-the-game" look. But I can't bag on him too much, seeing as how he provides each game with some much needed entertainment. Forget about driving to your local multiplex this summer to check out the new Batman or Indiana Jones flick. Watching Abreu trying to track down a fly ball in right field is all the adventure you need. Sometimes I swear I'm watching clips from the first ever slow pitch softball team I played on right after high school, a team whose only win came when our opponents forfeited because they couldn't drag enough players out of the bar in time for the game.

But enough of this. I'm tired of poring through numbers and splits trying to figure out why this Yankee team is currently one of the worst in baseball. Maybe it's something as bizarre as Giambi sharing his nasty gold thong with Jeter (I swear they both played extras as two of Steve Sanders' "Keghouse" frat-brothers on 90210). Or maybe it's something as simple as playing without the two most irreplaceable parts of the lineup (A-Rod and Posada) at the same time.

Whatever the reason, here's hoping they right the ship in time to make one more run at the old stadium. It would be a shame to think that one of the most historic landmarks in all of sports has seen it's last share of October baseball.

Come on, Yankees. Do it for history. Do it for tradition. Do it for honor. Do it for all the youngsters out there who look to you for inspiration. But above all this, do it for me next time I leave my Tier Reserved seats to go squat in the Loge section during the fifth inning. If I'm going to risk ejection from the stadium, I should at least get the chance to watch some quality baseball.

Is it June yet?

I think I can hear the boos crying out from across the Harlem River as the Yankees prepare to be swept out of their homecoming series by the surging Tigers (who haven't swept the Yankees in the Bronx since 1966!). Or maybe those are just groans of indifference at this point. Maybe the fans who chose to stick around past the seventh inning (although, once beer sales have commenced during a 4-run Yankee deficit, this fan says it's time to hop on the D-train) have attempted to inhabit the same zen-like attitude about this club that I have, repeating this mantra hundreds of times a day:

It's early. The bats will get hotter and the arms will get stronger. It's early.

Remember A-Rod's mantra a few years ago? Something about his bat head moving swiftly through the zone, or the importance of choosing the right stylist for doing highlights, or something like that? Well, he repeated it a thousand times every day, and it worked for him. If you don't believe me just check out his numbers every year, then check out how fabulous his hair always looks. You'll quickly see what I mean. Flawless, every time.

However, after what has taken place so far during this young season, I gotta say this mantra thing is really getting tested. It's gotten to the point where I basically can't let myself watch the games anymore, although I usually end up cheating and suffering through part of them anyway. It's like when I was a kid playing around with my friend's dog-shock collar. It hurt like hell, but I just couldn't stop pushing that button. 

I'm afraid that if things don't change soon, the experience of watching uninspired baseball will eventually become too comfortable, just as the experience of sending a significant amount of electric voltage through my nervous system did all those years ago. This is what I'm living with. This is my dilemma.

Is it me, or does every game that Chien-Ming Wang isn't pitching play out in essentially the exact same fashion? We'll call it the 2008 Yankees Formula: A - the starting pitcher with no command painfully labors through the lineup and can't get past the fifth inning, B - the floundering offense puts runners on base nearly every inning only to lose patience at the plate and fail to deliver a clutch hit, thus providing little or no run support for said pitcher, and C - the latest relief pitcher to be called up from Triple-A Scranton Wilkes-Barre comes in to mop up meaningless innings before shuttling back to SWB in exchange for the next fresh arm, leaving Joba and Mo (arguably the game's best late game combination) to sit on the bench and play Sudoku in the bullpen.

Watching a Yankees game these days is like being trapped inside the movie Groundhog Day, except without the charming, deadpan antics of Bill Murray wooing the lovely Andie MacDowell.

I think I have room for at least one more Yankees/pop culture analogy, although this one may be a bit more obscure. Ready? Watching a Robinson Cano at-bat is like watching old footage of "Stuttering" John Melendez interviewing a celebrity on the Howard Stern Show. During both instances the question becomes not if the whole thing will derail, but when and how. Like, will Larry King slap Stuttering John after fielding erectile dysfunction questions? Or merely escape into his limousine without answering? In Cano's case you may ask, will he swing at the first pitch and pop up to the shortstop? Or take two hittable pitches in the strike zone before hacking wildly at a slider in the dirt? 

Seriously, I haven't seen a hitter this uncomfortable at the plate since John Kruk faced Randy Johnson in the 1993 All-Star Game. I know Cano has proven to be a painfully slow starter that gets red hot in the second half, but this is getting almost impossible to watch anymore. Maybe he should start taking the first two months off every year. Randy Velarde is probably still playing somewhere out there, isn't he? Let's get him on the horn. Why not throw him out there for a few at-bats? Sure, he's been connected to Bonds and BALCO. Has that stopped us before?

But with all the injuries and poor play so far this year, just when you think the Yankees can't catch a break, they get a flash of good news: Phil Hughes will take his 0-4 record and 9.00 ERA to the disabled list until at least July. Hey Phil, (right, like he's reading this) just do me a favor. Use this time off as motivation to get back and help this team win, because the DL isn't a place you want to become too comfortable with. No matter what Carl Pavano tries to tell you, it's about as cool as Matthew McConaughey cruising for high school chicks in Dazed and Confused. Remember his hair?