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The 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.

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