MLB Free Agency: Barry Zito and 25 Free-Agent Checks GMs Wish Had Bounced

Matt TruebloodSenior Analyst IDecember 8, 2011

MLB Free Agency: Barry Zito and 25 Free-Agent Checks GMs Wish Had Bounced

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    The San Francisco Giants won the 2010 World Series on the strength of the best pitching staff in Major League Baseball. Barry Zito was not helpful in making that happen.

    In fact, Zito hasn't helped the Giants much at all since signing a seven-year, $126 million contract in December 2006. The deal has only penned the Giants in, making it hard to keep key players at some times and stifling the team's offseason aggression almost every year.

    The deal has become the punch line to dozens of baseball jokes, and the ultimate exemplar of why extreme caution must be taken when signing pitchers to long-term contracts.

    Of course, it's not as though Zito was the first or worst mega-deal in the relatively brief history of MLB free agency. Players get overpaid all the time, and some of those deals can hamstring the team who agrees to it, even costing GMs their jobs.

    Here are 25 such cases.

25. Wayne Garland

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    The natural bias in rankings of free-agent foibles is to emphasize those that cost their teams millions and hamstrung them for years, and indeed, the huge majority of this list consists of contemporary players. It's worth noting, though, that way back at the beginning of free agency itself, Wayne Garland made life harder for Albert Pujols.

    Garland was among the top tier of available pitchers in the first ever free-agent class, 1975-76. He had won 20 games for the Baltimore Orioles the year before, and many teams wanted him. The Cleveland Indians landed their man, but to do so, they gave him a 10-year contract worth $2.3 million.

    Garland pitched fairly well in 1976, though he lost 19 games.

    Beginning the following year, however, he posted park-adjusted ERA numbers 49, 18, 10 and 36 percent worse than league average, respectively.

    He retired in 1981, just halfway through the deal, but under the terms of the contract, still got his money.

24. Francisco Rodriguez

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    From his own perspective, Francisco Rodriguez could not possibly have had better timing. In 2008, he was in a walk year with the Anaheim Angels, and he saved a single-season record 62 games.

    He had a persona (K-Rod). He had the big numbers. At age 26, he even had youth on his side. 

    He hit the jackpot with the New York Mets. They needed a closer, and spent $37 million on Rodriguez for three years of his services. Thereupon, Rodriguez showed them the error of signing a relief pitcher to such a gaudy deal.

    Though he lost only a little in terms of big-picture effectiveness, Rodriguez saved fewer games in his first two seasons with New York combined than he had in 2008 alone. For the Angels, his career strikeout rate was 11.7 per nine innings. For the Mets, he fanned just 10 men per nine frames.

    Rodriguez was dealt to the Milwaukee Brewers in July, but first, he fought with a personal guest in the ballpark, and the general sourness of his deal at its end was a big reason Mets GM Omar Minaya got fired.

23. Vince Coleman

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    Thankfully, this isn't the crowd of fans into which Coleman threw a lit firecracker during his Mets career. But that happened.

    It was a microcosm of Coleman's impact from the moment he signed with the once-great Mets. Coleman played in fewer total games in 1991 and 1992 than he had in each of his first five big-league seasons individually. He stole fewer bases (99) in his three years with New York than he had in any of his first three individual seasons. He failed to come to the plate even 1,000 times in those three years.

    The Mets eventually had to eat the salary owed Coleman for the fourth and final year of his contract just to get back Kevin McReynolds in a post-1993 trade.

    During his three seasons in Flushing, the near-dynasty the Mets had built in the 1980s circled the drain, and two GMs came and went.

22. Adrian Beltre

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    This was not actually that bad a decision, and it could have worked out much worse than it did. After the 2004 season, Adrian Beltre was a free agent. He was 25 years old, coming off one of the best all-around seasons ever by a third baseman, and was ready to cash in on some huge numbers.

    Bill Bavasi was a year on the job as Seattle Mariners GM. He wanted to make a splash, and the Mariners were in a position to spend. When the market didn't even turn Beltre into much of a commodity, Bavasi jumped on him for five years and $65 million.

    It didn't work out.

    Beltre struggled to maintain average offensive production during his time in Seattle, and even after accounting for his defensive prowess, he had not a single star-caliber season there.

    He was not bad, but the narrative quickly soured on both he and Bavasi. The latter was fired before Beltre left town.

21. Juan Pierre

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    Too easily fooled by big counting numbers (hits and stolen bases, mostly), the Los Angeles Dodgers sprang to offer a five-year contract to Juan Pierre in the winter of 2006-07. They were also taken in by the appearance that Pierre was a good center fielder, a mirage created by the small dimensions of center field at Wrigley Field.

    Within a year, Pierre was in left field. By the end of his second season in Los Angeles, he was a role player behind Manny Ramirez.

    Pierre found playing time after being traded to the White Sox, and GM Ned Colletti somehow still has a job with the Dodgers. In the end, as is the norm, the only ones who got the shaft in Dodgertown were the fans.

20. Jason Bay

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    Like that of Francisco Rodriguez, Jason Bay's contract is one major reason Omar Minaya is no longer the GM of the New York Mets.

    Minaya gave Bay $66 million over four years, with a hefty fifth-year option that vests if the left fielder stays relatively healthy over the next two years. It was a risky signing even at the time, as Bay is a one-dimensional player who has occasionally struggled to stay on the field.

    That's been true so far, but it's not the only problem. In 910 plate appearances over two seasons, Bay has 18 home runs and 104 RBI for the Mets. For perspective, he had 36 bombs and 119 driven in for the Red Sox in 2009. His park-adjusted OPS is exactly average over the past two seasons.

    Bay simply has not lived up to this deal, and it's not even halfway over yet.

19. Esteban Loaiza

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    Years into a journeyman's career, Esteban Loaiza suddenly figured something out in 2003. That season, pitching for the Chicago White Sox, he won 21 games and posted a 2.90 ERA. He was then terrible for the Sox and New York Yankees in 2004, but good again in 2005 for the Washington Nationals.

    He made a bit less than $3 million pitching for the Nationals that season. After the year, though, in need of pitching help and looking for a bargain, Billy Beane and the Oakland Athletics took a shot at him. They signed him for three seasons and gave him $21 million.

    Loaiza struggled immediately. In 2006, he made 26 starts and ate some innings, but had a 4.89 ERA.

    If Beane was hoping Loaiza could put the A's over the top in October, Game 2 of the ALCS proved him wrong. The Detroit Tigers thumped Loaiza (seven runs in six innings) en route to a win and the AL pennant.

    In 2007, Loaiza made just two starts for the A's before (blessedly) the Dodgers selected him off waivers. That was another marked flop, and Loaiza would give it one last try with the White Sox, but in the end, he pitched only 219 innings over those three seasons. His ERA was 5.10.

    He never pitched again.

18. Andruw Jones

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    To most people, imminent decline was already written all over Andruw Jones when he hit free agency after the 2007 season. He had hit 26 home runs and won another Gold Glove award that year, but his overall batting line (.222/.311/.413) and his softening physique suggested that something had been lost.

    Ned Colletti jumped in with both feet anyway. By offering the best annual average value on the market, Colletti coaxed Jones into a two-year commitment to the Dodgers for a total of $36.2 million.

    It was unmitigated disaster from Day 1. In 2008, Jones played in 75 games, batted 238 times, put up a .158/.256/.249 batting line and played terrible defense. He was out to lunch, so much so that even the players' union did him no favors that winter.

    The Dodgers begged their way out of the second year of the deal, agreeing to pay Jones $3.2 million per year from 2009-14 instead of keeping him around. 

    How does Ned Colletti have a job, again?

17. Jason Schmidt

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    There were arm troubles in Schmidt's past already when he became a free agent after the 2006 season. He was also 34 years old. Still, Ned Colletti and his Dodgers signed Schmidt to a three-year, $46-million pact to try to nab the rival San Francisco Giants' ace starter.

    Schmidt pitched 10 times over the three ensuing seasons, totaling 43 innings and notching a 6.02 ERA. It should have been easy to foresee and avoid the ravages of decline, on some level at least, but Colletti saw Schmidt as a premium talent and signed him for big money anyway.

    He paid for it, albeit not with his job.

16. Jayson Werth

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    Seven years and $126 million is a huge investment in a player with just two seasons of regular playing time under his belt, but the Washington Nationals were looking to make a statement signing in the winter of 2010-11, and they homed in on their man quickly.

    Jayson Werth rewarded their faith poorly in his first year on the job, though, posting a below-average offensive season and proving he will not be able to man center field at all as this deal moves forward.

    The worst part of this deal, by the way, is its back-loadedness. Werth made just $10 million in 2011, actually a fair price for the 2.1 WAR he provided, according to Baseball-Reference. Beginning in 2012, though, his salary escalates, and he will make at least $20 million per year for the final four years of this deal.

    When Werth is wasting away as a left fielder and sixth hitter and Bryce Harper or Stephen Strasburg begin to pull in arbitration bucks, Nationals GM Mike Rizzo is going to regret this deal.

15. Jaime Navarro

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    After two very solid seasons with the Chicago Cubs, Jaime Navarro hit free agency for the third time in his career after the 1996 season.

    He was in a great position to find a good home. His ERA with the Cubs was a cool 3.62, an impressive number at Wrigley Field and amid an offensive explosion. He surpassed 200 innings in each of his two seasons with the Cubs.

    The Chicago White Sox needed pitching help. It only made sense that they pursue someone who already called the city home. Navarro signed for four years and $20 million, and White Sox fans were ecstatic.

    That did not last long. Navarro didn't even have the common decency to get hurt; he simply and suddenly stunk. In three seasons with the Sox, he pitched a sturdy 542 innings and had a 6.06 ERA. He had gone 29-18 during his time on the North Side; he went 25-43 for the South Siders.

    Navarro was someone else's problem by 2000, but by then he had ruined the White Sox pitching staff for far too long.

14. Russ Ortiz

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    Russ Ortiz was a mercurial performer on the mound at his best. In two different seasons, he led the league in walks. He could sometimes be effective anyway, but his ERA numbers from 1999-2001 perhaps tell the story best: 3.81, 5.01, 3.29.

    That was the kind of man in whom the Arizona Diamondbacks knew they were investing in 2005. Still, the upside risk was worth it in the eyes of new Arizona GM Josh Byrnes. He signed Ortiz less than two months after taking the job, giving him $15.25 million over two years.

    It was a nasty housewarming gift. Ortiz pitched 28 times for the Diamondbacks in a year and a half, toting a 7.00 ERA and walking 20 more batters than he struck out. Arizona eventually released Ortiz in June of 2007, eating the remaining money on his contract.

13. Milton Bradley

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    Riding high off back-to-back NL Central titles, the Cubs felt they could handle a bit of a personality risk when they inked MIlton Bradley to a three-year, $30-million deal beginning in 2009.

    Maybe they could have; we'll never know.

    Bradley was not "a bit" of a personality risk. As it turned out, he was the rare exception to the rule that considerations of chemistry should always be subjugated to considerations of talent in selecting players. Bradley was such a distraction, and at times, such an airhead, that even his .378 OBP could not save him.

    The Cubs traded him after one year, but the black mark remained on the record of Cubs GM Jim Hendry until the day he was fired.

12. Albert Belle

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    Albert Belle was one of the best sluggers of the late 1990s, but is ill-remembered because of his temper, attitude and early retirement. It's the last of those that most directly impacts this piece.

    Belle became a free agent in autumn 1998 after the Chicago White Sox declined to make him one of the three highest-paid players in baseball. He then signed a five-year deal with the Baltimore Orioles, making him the highest-paid player in baseball.

    Belle got his way, but only two years into the deal, things fell apart. A hip condition drove Bell out of the game. Baltimore had taken out an insurance policy on Belle and was able to avoid sunk costs for the most part, but in order to do so, they had to keep Belle on their 40-man roster as dead weight.

    This is the epitome of a contract that hamstrings the team who agrees upon it.

11. John Lackey

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    A year after watching the Yankees overpay A.J. Burnett but turn it all into a World Series title, the Red Sox figured they could sneak another one past the baseball gods. They signed John Lackey to a deal (five years, $82.5 million) identical to the one Burnett had signed.

    The results have not been as worthwhile. Lackey struggled a bit in 2010, mightily in 2011 and has gotten tangled in a series of mini-controversies this past year.

    From the chicken and beer in the clubhouse to his unfortunately public divorce to Tommy John surgery that will shelve him for all of 2012, reality has conspired against the vision the Red Sox had when they signed Lackey.

    With three more years to go on the deal, things might only get worse.

10. Gary Matthews, Jr.

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    Already 32 years old and with just a single year of productive, regular experience under his belt, Gary Matthews wasn't exactly commanding the huge bucks. Unfortunately, Tony Reagins and the Angels were dead-set on giving it to him, anyway. 

    Matthews got $50 million over five years, virtually all of it paid by the Angels even after they traded him away. For that, he returned a total of 30 home runs and a .708 OPS, with poor defense in the outfield.

    His game totals by year over the life of the contract, beginning with 2007: 140, 127, 103, 36, 0.

9. Todd Hundley

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    It's by no coincidence that signing Todd Hundley to a four-year deal worth in excess of $20 million was one of the final acts as Cubs GM by Ed Lynch. That move alone derailed what the Cubs were trying to build at the time.

    Hundley brought a cloud over the clubhouse (literally; he was caught smoking in smoke-free areas of that room and of the dugout) and hung there for two years.

    Son of long-time Cub Randy Hundley, Todd had hoped he could come home and be a conquering hero. He never adjusted to adversity, though, and it wasn't long before the booing got to him and he folded like a cheap suit.

    Halfway into the deal, Chicago somehow dumped him on the Dodgers, and got useful veterans in return. Ed Lynch was by then only a distant voice, buried in the scouting department.

8. Denny Neagle

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    When Denny Neagle got $32 million over four seasons to join the Colorado Rockies for the 2001 season, it was one of the most immediately obvious overpays in recent memory. As was quickly pointed out, Neagle was two years removed from his last productive season, 1998. In 2000, he had flopped (to the tune of a 5.81 ERA) after a mid-season move to the New York Yankees.

    How would he succeed in Colorado?

    As it turned out, he wouldn't. Neagle was out of baseball by the middle of the third year of the deal, prior to which he ran up a 5.57 ERA and a 19-23 record in 370 innings for the Rockies.

7. Mo Vaughn

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    Wayne Garland might have been the first 10-year contract washout, but Prince Fielder has Mo Vaughn to thank for most of his problems getting the market excited. Vaughn went before Fielder in the lineage of great fat first-base sluggers, and did not acquit himself well.

    After years of dominance with the Red Sox, a 31-year-old Vaughn signed for six years and $78 million with the Angels after the 1998 season. He was more or less his usual self the following year, but the dual problems of being immobile and somewhat vulnerable to wear and tear became apparent pretty quickly.

    Vaughn played in only four of the six years covered by the deal, and hit just 98 home runs.

6. David Winfield

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    After all, this article is about checks GMs wish had bounced, and no contract gave fits to more GMs than this one. George Steinbrenner pressed for his team to acquire David Winfield, who was already one of baseball's best hitters when he came aboard after the 1980 season.

    But things quickly turned sour. Winfield had negotiated a deal whereby his salary would be indexed to inflation, effectively doubling the originally agreed-upon value of the contract.

    Steinbrenner was livid. He fired Gene Michael, who had made the deal, and began to assume an even more intrusive level of influence over his team's maneuvers. Before Winfield was traded in 1990, six more men came and went from the GM's chair at Yankee Stadium.

5. Darren Dreifort

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    If you are beginning to see the primary premise of this article, raise your hand. It's simple: Don't hand out free-agent mega-deals to pitchers, unless they are Hall of Fame-caliber and in their prime.

    Otherwise, the risk is simply too great.

    The Dodgers' decision to sign Darren Dreifort for five years and $57 million prior to the 2001 season was ridiculous. Dreifort hadn't been worth anything close to that amount up to that point, and was already approaching 30. He might have been fairly expected to be a good mid-rotation innings eater, but nothing more, and what happened in reality should not fairly surprise anyone.

    Dreifort pitched just 205 innings for the Dodgers over the life of the contract. He made only 26 starts and 60 relief appearances. He had a 4.64 ERA, and although his stellar strikeout rate suggests he could have done a bit better, he struggled to get the ball in the zone.

    It was a nightmare on every front, and the Dodgers should have seen it coming.

4. Bobby Bonilla

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    What a mess Bobby Bonilla's time in New York turned out to be. He made $29 million or so on his first deal with the Mets, but hardly earned it. He was the highest-paid player in the National League from 1992-94, but his total WAR over that span was a modest 8.0.

    That was bad enough. The Mets traded Bonilla in 1995 and ought to have simply left bad enough alone. Instead, they reacquired Bonilla in 1999. He put up a .160/.277/.303 line for them in 141 plate appearances that season, and it was clear he was done in New York.

    Now came the other big mistake. The Mets had only to fork over Bonilla's $5.9 million and say goodbye to him forever.

    Instead, they arranged this settlement. They would pay his money over 12 more years, with the balance getting eight percent compound interest annually.

    In the end, they paid him an extra $25 million just to go away for the 2000 season and post a .356 OBP for the rival Atlanta Braves.

3. Alfonso Soriano

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    Soriano gave the Cubs two terrific seasons at the front end of this deal. He led them to back-to-back NL Central titles. He is too much maligned for his inability to get on base (we knew that all along) and for his defense (it's not as bad as you think).

    Still, this deal was an overreach, a classic case of an executive (Jim Hendry, in this case) getting the go-ahead to spend money and doing it too brazenly. Soriano is not a clubhouse poison or a poor teammate or a lazy worker, but he has been unable to live up to a contract that he never should have received.

    That's one big reason Jim Hendry is no longer in the big chair.

2. Barry Zito

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    At the time Barry Zito signed it, this was the largest contract ever given to a pitcher. Think about that. Yes, Zito had won a Cy Young award a few years earlier, but by the time he hit free agency, he was far short of an elite hurler. He certainly wasn't bullet-proof.

    The investment profile said, "No," but the Giants read, "Go."

    The deal has never looked worse than it does right now. At least for a few years, Zito chewed up innings at the back end of that terrific Giants rotation. In 2011, he had a 5.87 ERA in just 53 innings of work.

    With two seasons left on the deal, the Giants remain hamstrung by a poor decision they made a half-decade ago.

1. Mike Hampton

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    This is the contract Zito took down, by however slim a margin, and even though it happened six years later. Hampton got eight years and $121 million from the Colorado Rockies in the winter before the 2001 season. His fly-ball tendencies hurt him badly in Coors Field, though, and the Rockies watched in horror as their prized investment collapsed.

    Hampton would last just two years in Colorado, with an ERA of 5.75—two runs and change higher than his career ERA before signing on.

    A trade delivered Hampton to Florida, then Atlanta, during November 2002, but the Rockies were left holding the bag for the huge majority of the contract to which Hampton could not live up.