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7 Overpaid Yankees That Nearly Tanked the Club

The lousiest players and biggest cheats to ever wear pinstripes, via Filip Bondy’s ‘Who’s on Worst?’

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Baseball players getting wildly overpaid is a modern-era phenomenon, born from free agency and George Steinbrenner's checkbook. There's no shortage of examples, but don't expect to see any names here dating before 1974. Back then, wads of money weren't being thrown at anybody, regardless of merit. Now, players enter contract years knowing full well they may strike it rich with one well-timed season. More often, general managers like the Yankees' Brian Cashman regret these pacts just four or five months after the ink dries. (That would be you, Alex Rodríguez.) One hard-and-fast rule: nobody admits publicly to a mistake until the next GM takes charge. Until now. Here's a look at the most egregious examples on the Yankees, as explained in Filip Bondy's book Who's on Worst?

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Carl Pavano (2005; 2007–2008)

Pavano's misadventures in pinstripes quickly became mythic. After a respectable start in 2005, he injured his right shoulder and headed for the disabled list. Then he suffered a bruised buttocks – the butt of many jokes – during spring training in '06 and headed back to the DL. Pavano was still recovering from his odd ailment in August when he fractured two ribs ramming his Porsche into an eighteen-wheeler in Florida. At least Yankees fans got a few last chances to boo the guy: Following a visit from Torre and the trainer in the sixth inning of a game on September 14th, 2008, Pavano limped to the dugout and was inundated with jeers. In his final appearance on September 25th, Pavano gave up five runs on eight hits in three and two-thirds innings. During his years in the Bronx, Pavano pitched a total of 145 and 2/3 innings, never posting an ERA under 4.76 in any of those abbreviated seasons. The Yanks had paid him nearly $261,000 for every inning pitched, or about $4 million per injury.

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Jason Giambi (2002–2008)

Three months after 9/11, New York's economy was imploding and nobody was in the mood for showmanship. Thus Giambi, through no fault of his own, became a symbol of corporate gluttony. His impressive bat speed and power numbers remained, but his averages swooned to .250 in 2003 and .208 in 2004. His declining offense wasn't the whole story, though: He brought scandal to the Bronx, becoming a big part of the BALCO steroid probe. During Giambi's years with the team, he hit 209 homers – or very nearly 30 per season – and drove in 604 RBIs. Yet his arrival, in many eyes, was the very moment when the Yanks jumped the shark. By 2007, the team's streak of nine straight American League East titles was broken while the club's payroll stood at a gaudy $218.3 million, an increase of more than 350 percent from the pre-Giambi era.

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Ed Whitson (1985–1986)

Whitson became a free agent after he went 14-8 with a 3.24 ERA for the San Diego Padres in 1984. But after signing his five-year, $4.4 million contract – a major investment for the time – Whitson went 1-6 with a 6.23 ERA over his first eleven starts in New York. The fans jeered him mercilessly and hate mail arrived by the bundle as it became clear that Whitson was not one of those guys who could shrug off harsh criticism. Later he would only start games on the road and appear in relief at Yankee Stadium. This didn’t work either. Over less than two seasons, Whitson was 15-10 but had a 5.38 ERA. Years later, Whitson told ESPN of his frustrations with New Yorkers: "It's like working in an office and your boss comes in and says, 'You suck' after you've tried your best," he said. "Now multiply that by 50,000."

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Kevin Brown (2004–2005)

Back in 1998, Brown signed the first $100 million–plus contract in baseball, agreeing to a seven-year, $105 million deal with the Dodgers. While Brown had posted many lights-out seasons with his sinking fastball, he was already 33, which meant the contract would endure past his 40th birthday. The Dodgers' investment appeared overgenerous, but the Yankees came out looking far worse when they traded for Brown and the final two years on his contract in December of 2003. The Dodgers had managed to squeeze two or three decent seasons out of Brown before the Yankees went on the hook for $31.4 million with the fading starter. And the team got exactly what they deserved for such foolishness. Brown went 14-13 with an ERA of 4.95 over his two seasons in the Bronx.

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Javy Vazquez (2004; 2010)

In the middle of the first decade of the twenty-first century, when the Yankees were desperate to reestablish a dynasty, they overpaid Randy Johnson (a disappointment) and Kevin Brown (a disaster). But Vázquez stood out if only because the Yanks failed to learn their lesson. The club acquired Javy before the 2004 season and signed him to a four-year, $45 million contract. "I want to be a Yankee for more than a year," Vázquez said. But one year was all that could be tolerated. The Yanks paid him $9 million before dealing him to the Diamondbacks. Later, in December 2009, Brian Cashman was desperate to extend his rotation and believed that Vázquez still had enough stuff to thrive. The team ignored history and agreed to pick up his $11.5 million salary for one season. Yet again, nothing went right. He struggled to produce a record of 10-10 with a 5.32 ERA. His cumulative stats over two seasons: 24-20 with a 5.09 ERA. For these performances, Cashman had laid out $20.5 million, or nearly $1 million per victory.

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Hideki Irabu (1997–1999)

Hideki Irabu, the six-foot four-inch giant who owned a wicked 98-mile-per-hour fastball, was drafted at age seventeen and began playing for Japan’s Lotte Orions in 1987. Eventually, in January of '97, his negotiating rights were sold to the San Diego Padres. But he demanded a bigger stage and fancied himself a Yankee. So Irabu forced a deal, signing a four-year contract in the Bronx for $12.8 million. Before the year was done, Irabu was sent down to the minors for a spell and finished his first major-league season with a 7.09 ERA. The following season was more hopeful, as he posted a 13-9 mark with a 4.06 ERA. But by this time, it was obvious Irabu would never meet the oversized expectations that burdened him. The team dealt him to Montreal at the end of the season. Irabu was a failure with the Expos and later the Rangers, and returned to Japan a defeated man.

Excerpted from Who's on Worst? by Filip Bondy. Copyright © 2013 by Filip Bondy. Excerpted by permission of Anchor, a division of Random House LLC. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

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