MLB Free Agency: Worst Free Agent Signings in Each Team's History

Avi Wolfman-Arent@@awolfmancomethCorrespondent IIOctober 22, 2011

MLB Free Agency: Worst Free Agent Signings in Each Team's History

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    I come today with proof that everyone, indeed, makes mistakes.

    Since Major League Baseball instituted the orgy of instant gratification known as free agency in the mid-1970s, every team has at some point succumbed to its seductive bounty against their better judgment.

    The beauty and hazard of free agency is that it doesn’t ask teams to wait.

    It simply says: “Come with the cash and I’ll give you your man.”

    For the impatient, the imprudent and the downright stupid, that deceptively simple arrangement doubles as a trap. And a general manager who operates with his job danging above his head generally fits all three of those dubious categories.

    Not surprisingly, the price paid is often far too high.

    So before you harangue the local radio station with demands that your team pay top dollar for a free-agent-to-be, consider the graveyard of ghoulish deals that follow.

A Bit of Explanation

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    There are two types of bad free agent deals.

    I’ll call the first the “Mike Jackson explosion,” wherein a player signed to short-term deal never plays or plays very sparingly for the team that signed him. Because teams who sign marquee free agents usually give those players ample time to prove themselves (and vindicate the team’s faith in their skills), “Mike Jackson explosions” are generally limited to short contracts.

    The second is the “Alfonso Soriano slow burn,” wherein a player performs well below the value of a painfully long contract. Sometimes these players post serviceable numbers, but nothing that justifies their pay. Once this becomes clear, such contracts are near impossible to move and a team is stuck with a prohibitive sunk cost.

    Unlike the first type of bad deal, the “slow burn” can impact the club’s outlook for a decade or more. They can cause a team to make bad compensatory moves or, at the very least, severely limit their financial flexibility when addressing other roster deficiencies.

    As you’ll see in this list, I lean towards the “slow burn” when considering which contracts qualify as the worst. The examples of Mike Jackson and Alfonso Soriano help make my case.

    Coming off two decent seasons as Cleveland’s closer, the Philadelphia Phillies signed 35-year-old reliever Mike Jackson to a one-year, $3 million deal in 2000. Jackson experienced discomfort warming up for his first appearance as a Phillie and missed the rest of the season. He would never throw a pitch for Philadelphia.

    You could argue Jackson’s was a terrible contract because the Phillies got almost no return on their investment. And you’d be right.

    Still, the long term effects on the franchise were essentially nil. The Phillies were likely going to spend that $3 million anyway, and Philadelphia fans will tell you that the 2000 team was more than a decent set-up man short of glory.

    The Chicago Cubs, however, must continue to grapple with a contract that keeps Alfonso Soriano in their employ through 2014. It’s hard to quantify how many other personnel moves that contract influences, but the net deficit (prospects spurned, supporting players signed, trades nixed) will eventually loom much larger than whatever loss the Phillies incurred on Mike Jackson.

    Did Alfonso Soriano play better in a Cubs uniform than Mike Jackson in a Phillies uniform? Of course.

    Does that mean Soriano’s contract was somehow better than Jackson’s? Not at all.

Arizona Diamondbacks: Russ Ortiz

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    Contract: Four years, $33 million (2005)

    Sad Stats: 5-16, 7.00 ERA, 67:87 SO:BB ratio


    The Lesson: Don’t sign pitchers on the wrong side of 30 and expect big things.

    Russ Ortiz hadn’t had as much as a scratch when the Diamondbacks signed him in 2005. In the pitiful year-and-a-half that followed, Ortiz suffered injuries to his ribs and calf that accelerated his decline and ultimately made him one of the biggest free agent busts in history.

    Even when he was healthy, Ortiz struggled to keep the ball in the ballpark and rarely missed bats. Midway through the 2006 season the Diamondbacks released Ortiz with $22 million still remaining on his contract. It was, at the time, the most money remaining on any MLB contract at the time of release.

    Dishonorable Mention: Todd Sottlemyre, Eric Byrnes

Atlanta Braves: Bruce Sutter

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    Contract: Six years, $10 million (1985)

    Sad Stats: 4.55 ERA, 152.1 innings pitched, retired following 1988 season

    The Lesson: Don’t sign heavily used relievers through their 37th birthday.

    Hall of Famer Bruce Sutter came to the Atlanta Braves as one of the best relievers in baseball. A few years and a torn rotator cuff later, Sutter was out of the game. The Braves, like many teams after them, would discover that relievers are rarely worth big bucks and almost never good bets for long-term deals.

    When there’s plenty of good talent available for cheap in the minor leagues, splurging for a top-flight reliever doesn’t make sense.

    Dishonorable Mention: Al Hrabosky, Kenshin Kawakami, Vinny Castilla

Boston Red Sox: Julio Lugo

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    Contract: Four years, $36 million (2007)

    Sad Stats: .319 OBP, 10 HR, 42 Errors

    The Lesson: Quit it with the aging shortstops already.

    After whiffing on a four-year deal for Edgar Renteria and quickly trading him to the Atlanta Braves, the Red Sox took another shot at a veteran middle infielder in the winter of 2006 and surfaced with former Devil Ray Julio Lugo. Lugo managed to out-suck Renteria, matching the latter’s fielding ineptitude but adding to it a layer of total offensive incompetence.

    The Red Sox traded Lugo to the St. Louis Cardinals midway through 2009. The Red Sox ultimately covered most of Lugo’s remaining contract while he played it out with the the Cardinals and Baltimore Orioles.

    Dishonorable Mention: Edgar Renteria, Matt Clement, Daisuke Matsuzaka, John Smoltz, Matt Young

Baltimore Orioles: Albert Belle

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    Contract: Five years, $65 million (1999)

    Sad Stats: Played just two seasons in Baltimore, probably set some sort of record for alienated teammates

    The Lesson: Steer clear of malcontents.

    Albert Belle’s legacy is less about numbers than it is about sentiment. Albert Belle was, well, a jerk. He clashed with teammates, ignored coaches and during his two years in Baltimore often refused to take batting practice with the team.

    He performed well enough during his two seasons in Baltimore, but a degenerative hip ailment forced an early retirement. The Orioles paid Belle the majority of his contract after he’d already left baseball. That combined with the rude ‘tude make Belle the worst signee in Orioles history.

    Dishonorable Mention: Sidney Ponson

Chicago Cubs: Alfonso Soriano

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    Contract: Eight years, $136 million (2007)

    Sad Stats: 109 OPS+, .266/.320/.498 slash line

    The Lesson: Eight years is a long time, especially for a guy who doesn’t walk.

    Among a flurry of terribly short-sighted deals by the Chicago Cubs, Soriano’s stands out as the most myopic. Eight years for a player with zero plate discipline makes little sense, especially when that player just turned 31.

    Even with decent power numbers, Soriano’s game is so one-dimensional it’s hard to imagine how the team can work around the rest of his contract (which runs through 2014). What’s worse, Soriano has a full no-trade clause that makes the slimmest of trade hopes even slimmer.

    The Cubs will jettison Ryan Dempster’s mega contract this winter and Carlos Zambrano’s after 2012. Soriano, and his slipping OBP, will stay with this team well into the Theo Epstein era.

    Dishonorable Mention: Carlos Zambrano, Ryan Dempster, Milton Bradley, Todd Hundley

Chicago White Sox: Jaime Navarro

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    Contract: Four years, $20 million (1997)

    Sad Stats: 25-43, 6.06 ERA

    The Lesson: Two good years do not a pitcher make

    With Adam Dunn fast approaching, Jaime Navarro still holds the title for worst free agent signing in Chicago White Sox history by the slimmest of margins.

    Navarro began his career with the Brewers, alternately struggling and succeeding through six tumultuous seasons. He left Milwaukee for a two-year stint with the Chicago Cubs, putting together a pair of solid campaigns with and ERA less than 4.00 in each.

    That brief bit of consistency suckered the crosstown White Sox into making Navarro their highest paid pitcher. The plan quickly backfired and Navarro didn’t last past the 2000 season.

    Dishonorable Mention: Adam Dunn

Cincinnati Reds: Eric Milton

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    Contract: Three years, $25.5 million (2005)

    Sad Stats: 5.83 ERA, 73 HR, 77 ERA+

    The Lesson: Fly ball pitchers and home run parks do not mix

    His first year in Cincinnati, Eric Milton led the league with 40 home runs allowed. That’s about all you need to know of Milton’s time as a Red.

    He couldn’t keep the ball out of the air and his dreadful 0.43 career groundball-to-flyball ratio played poorly in hitter-friendly Great American Ballpark. He mercifully missed most of his last season in Cincy with an elbow injury and never pitched as a regular starter in the big leagues again.

    Dishonorable Mention: Jimmy Haynes, Willy Taveras

Cleveland Indians: Wayne Garland

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    Contract: 10 years, $2.3 million (1977)


    Sad Stats: Just five more years in baseball, including two with less than 60 innings pitched

    The Lesson: Kids, don’t trail blaze.

    In a far more innocent time, when free agency was young, the visionaries over in Cleveland thought they’d experiment a little. It was the 1970s after all, and a little experimentation never hurt anybody.

    Until it did...

    When Indians executive awoke from their haze, they discovered they’d just signed a guy named Wayne Garland to a 10-year contract. Oops.

    Cleveland paid dearly for their innovative thinking when Garland, who had one 20-win season in Baltimore, injured his rotator cuff and retired after the 1981 season

    After that baseball executives decided to lay off the 10-year contracts, at least for a while.

    Dishonorable Mention: Keith Hernandez, David Dellucci

Colorado Rockies: Mike Hampton

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    Contract: Eight years, $121 million (2001)

    Sad Stats: All of them (besides the hitting ones)

    The Lesson: Make your mistakes early.

    Mike Hampton’s contract needs little introduction. It’s widely regarded as the worst free agent contract in baseball history, a $100 million mistake that saw Hampton’s ERA explode in the high altitude of Coors Field over two abysmal seasons.

    I find it more amazing that the man who signed Hampton’s contract, Dan O’Dowd, is still Colorado’s general manger. Somehow surviving the horrific deals he gave Hampton and fellow pitcher Denny Neagle in 2001, O’Dowd persevered to build the best Rockies teams in the franchise’s short history.

    Dishonorable Mention: Denny Neagle

Detroit Tigers: Dean Palmer

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    Contract: Five years, $35 million

    Sad Stats: 60 hits over the final three seasons

    The Lesson: Everything the Tigers did around the turn of the 21st century went horribly wrong.

    In 2003, when the Detroit Tigers hit their 119-loss nadir, Dean Palmer was there.

    Or, he was kind of there.

    He was there in the sense that he was the team’s second-highest-paid player. He wasn’t there in the sense that he played in just 26 games and hit .140 with zero home runs.

    After hitting well in the first two years of his contract (a common theme on this list), the former Ranger limped through the last three years of his deal. Over those campaigns Palmer played in just 87 out of a possible 486 games and slugged a paltry 11 home runs.

    Even under the assumption that a hitter on the wrong side of 30 will get overpaid toward the end of a given mega-deal, Palmer’s underperformance stands out.

    Dishonorable Mention: Fernando Vina, Mike Moore, Bill Gullickson (Part II), Steve Sparks

Houston Astros: Carlos Lee

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    Contract: Six years, $100 million (2007)

    Sad Stats: OPS under .800 in 2010 and ‘11 seasons, declining home run totals in each successive year of contract

    The Lesson: Avoid man boobs

    Those pursuing Prince Fielder this offseason ought to consider the case of Carlos Lee and the Houston Astros.

    From 2003 to 2006 Lee was as lock down a 30 home run candidate as you could find. And despite persistent whispers that his potato sack body would eventually catch up with him, the Astros threw a bunch of years/money at the left fielder in hopes that his consistent production would fortify a line-up already featuring Lance Berkman.

    For the first couple of years it worked, until Lee hit 33 and his sagging frame led to injuries and reduced bat speed. Now, as the Astros unload their other veteran players and turn to the future, they must continue to bite the bullet on the Panamian slugger through 2012. Lee and his contract are as untradeable as they come.

    Dishonorable Mentions: Greg Swindell, Kaz Matsui, Woody Williams

Kansas City Royals: Mark Davis

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    Contract: Four years, $13 million (1990)

    Sad Stats: 7 saves, 5 blown saves as a Royal

    The Lesson: Never make a reliever the highest paid player in baseball history.

    At the height of the closer craze, surrounded by Dennis Eckersley, Lee Smith and Nasty Boys, the Kansas City Royals were so desperate for a ninth inning man they extended an unthinkably large contract to San Diego reliever Mark Davis. Four years and $13 million, a deal that gave Davis the highest annual salary in major league history.

    Davis never had an ERA under 4.00 as a Royal.

    It was a Waterloo moment for closers in baseball, as Davis’ eventual failure in Kansas City would expose the folly of privileging one-inning specialists The man responsible for the move was then-Royals GM John Schuerholz, architect of the Atlanta Braves dynasty and one of the most revered executives in baseball history. Even the best make mistakes.

    Dishonorable Mention: Gil Meche

Los Angeles Angels: Gary Matthews Jr.

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    Contract: Five years, $50 million (2007)

    Sad Stats: 30 HR, .708 OPS, -0.6 WAR

    The Lesson: When a guy hits 50 points higher than his career average in a contract year, sniff around a little

    After an inexplicably good contract year in which he hit .313 with a career-high 19 home runs, the Los Angeles Angels (then “of Anaheim”) signed outfielder Gary Matthews Jr. to a mammoth five-year contract.

    Matthews Jr. would never come close to replicating those numbers and soon found himself out of the Angels starting line-up. Los Angeles eventually ate all but $2 million of the contract in order to trade Matthews to the Mets after just his fourth season on the Halos.

    To make a bad contract worse, it would surface a few months after Matthews Jr. signed the deal that he was involved in an ongoing HGH investigation. Matthews Jr. denied the charges, but for many it explained that “inexplicably good contract year” in perfect clarity.

    Dishonorable Mention: Mo Vaughn

Los Angeles Dodgers: Don Stanhouse

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    Contract: Five years, $2.1 million (1980)

    Sad Stats: 5.04 ERA, played just one year with L.A.

    The Lesson: The Dodgers are terrible at free agency

    Between the Jason Schmidt travesty, the Darren Dreifort fiasco, the Kevin Brown imbroglio, the Manny Ramirez charade and the Andruw thing, the Dodgers made it hard on me to pick just one bad free agent contract. There aren't enough words that describe just how bad this franchise has been in the open market.

    I went with Don Stanhouse because that deal seems the most imprudent from a “well what did you expect?” standpoint.

    For starters, Stanhouse was never all that good. Baltimore manager Earl Weaver called him “full pack” because Stanhouse’s shaky pitching caused the manager to rip through cigarettes in the dugout. As an Oriole in 1978, Stanhouse managed a 2.89 ERA despite a 1.50 WHIP. If WHIP was a statistic in 1978, the Dodgers would have known what many other teams intuited.

    Bad times were ahead for Stanhouse.

    Karma caught up with Stanhouse in L.A., and he played just one season in Dodger blue.

    Dishonorable Mention: Too many to name, but let’s start with Jason Schmidt, Manny Ramirez, Juan Pierre, Andruw Jones, Darren Dreifort, Kevin Brown

Miami Marlins: John Burkett

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    Contract: Two years, $7 million (1995)

    Sad Stats: 20-24, 4.31 ERA

    The Lesson: The Marlins are pretty good at free agency.

    The Florida/Miami Marlins haven’t made too many big free agent signings in their brief history, and the ones they have made worked out pretty dang well.

    The 1997 Word Champion Marlins are a prime example of the organization’s free agent savvy. The decision to sign Bobby Bonilla, Devon White, Moises Alou, Livan Hernandez, Kevin Brown, Alex Fernandez and Al Leiter all within a couple of seasons turned up roses. That team remains the only championship club built almost exclusively through free agency.

    The only questionable signing I found amid Miami’s mid-90s spending spree was that of John Burkett. The starter never matched his numbers in San Francisco and the Marlins unloaded him to the Rangers with a half-year left on his contract.

    Dishonorable Mention: Miguel Olivo, John Buck

Milwaukee Brewers: Eric Gagne

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    Contract: One year, $10 million (2008)

    Sad Stats: 5.41 ERA, 10 saves in 17 opportunities

    The Lesson: Wait until after the Mitchell Report to do your offseason shopping

    I imagine the scene went something like this:

    Doug Melvin arrives for work, sits down in his leather chair and scans the mahogany desktop for something to read with his morning coffee. “Ah, the Mitchell Report,” he says to himself. “I’ve been expecting this.”

    Excitedly thumbing through its contents like a preteen would a slam book, his giddy expression turns to horror when he sees the name “Eric Gagne” printed in bold block letters across the opening page.

    That Eric Gagne? The one Melvin signed just days ago to a $10 million deal?

    Melvin reflexively spews a mouthful of coffee over the paper clipped pages. He pages his secretary, “Order three dozen donuts,” Melvin rasps into the intercom. “It’s time for Doug Melvin to eat his feelings.”

    Dishonorable Mention: Jeff Suppan

Minnesota Twins: Rondell White

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    Contract: Two years, $5 million (2006)

    Sad Stats: 11 HR, .261 OBP

    The Lesson: Don’t be fooled by a veteran’s last gasp.

    With 34-year-old Rondell White coming off a surprising 2005 campaign with the Detroit Tigers, Minnesota penned the aging slugger in hopes that he would replace the departed Jacque Jones.

    As it turned out, the brief uptick in Detroit was merely an illusion tacked onto the end of a standout career. White barely survived two seasons in Minnesota and quietly retired at the end of 2007.

    Dishonorable Mention: Tsuyoshi Nishioka, Tony Batista, Terry Steinbach, Bob Tewksbury

New York Mets: Bobby Bonilla

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    Contract: 5 years, $29 million (1992) AND deferred payments from 1999


    Sad Stats: The Mets owe Bonilla almost $30 million total over the next 24 years, for real

    The Lesson: Bobby Bonilla is both wise and patient. The Mets are neither.

    So technically the $30 million the Mets owe Bobby Bonilla over the next 24 years stems from a trade they made with the Los Angeles Dodgers, and not from the awful free agent contract they awarded him in 1992.

    But the sheer lunacy of it all demands our attention on a list like this.

    Round 1: The Mets signed Bonilla to a huge free agent contract in 1992 and the deal quickly turns sour. Bonilla performed worse than expected and proved even less reliable as a teammate.

    Round 2: The Mets, for reasons unknown, trade for Bonilla in 1998 while he’s under contract with the Dodgers (on a deal he originally signed with Florida). He performs even worse than in the first go-round and behaves like even more of an ass. The Mets are so desperate to wipe their hands of him before the 2000 season that they arrange to defer payments on his contract until 2011, with interest.

    Round 3: With the Mets in dire financial straits, they began paying Bonilla an annual salary of just under $1.2 million in 2011. Bonilla will remain on Mets payroll until 2034.

    Ladies and gentlemen, the New York Mets.

    Dishonorable Mention: Vince Coleman, Oliver Perez, Kaz Matsui, Luis Castillo

New York Yankees: Carl Pavano

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    Contract: Four years, $39.95 million

    Sad Stats: Nine wins, 5.00 ERA

    The Lesson: None, none at all.

    When you spend, and spend, and spend like the Yankees do, there are bound to be plenty of mishaps. Pavano’s injury plagued career in pinstripes, coupled with his struggles as a teammate, made him the poster child for Yankee free agent follies, but plenty of others could stand in his place.

    The point is the Yankees really don’t care. They can afford to pay Carl Pavano more than $4 million per win because there’s always a backup plan and more cash waiting in the bank if they should need it.

    Dishonorable Mention: Dave Collins, Kei Igawa, Jason Giambi, Jaret Wright, Hideki Irabu, Alex Rodriguez

Oakland Athletics: Ruben Sierra

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    Contract: Five years, $30 million (1993)

    Sad Stats: Two full seasons in Oakland and never eclipsed a .300 OBP, -1.7 WAR

    The Lesson: Make sure your free agent can reach base

    Coming off a breakout year with the Texas Rangers, the Oakland Athletics traded for Ruben Sierra midway through 1992. They were so enamored with his .277 average and three home runs in 27 games that they decided to lock him up long term the following offseason.

    The deal made Sierra the highest paid player on an A’s team that included Mark McGwire, Dennis Ecksersley and Rickey Henderson. Overvalued because of his tools and raw power, Sierra’s inability to reach base consistently stung an Athletics organization on its way down from the halcyon years of the late 1980s and early 1990s.

    The A’s would eventually trade Sierra to the Yankees for Danny Tartabull when the former was in just the third year of his contract.

    Dishonorable Mention: Esteban Loaiza, Dave Kingman, Bill Caudill, Ben Sheets

Philadelphia Phillies: Adam Eaton

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    Contract: Three years, $24 million (2007)

    Sad Stats: 74 ERA+, 1.34 SO:BB

    The Lesson: Never try to reignite an old flame.

    At the end of the 1999 season, the Phillies traded top pitching prospect Adam Eaton to the San Diego Padres for veteran hurler Andy Ashby. Ashby was a non-factor in just a half-season spent with the Phillies, but the sour taste was largely mitigated by the fact that Eaton never manifested any of the promise he’d inspired as a prospect.

    In six seasons spent with the Padres and one with the Texas Rangers, Eaton never surpassed mediocrity and often lounged far below even that. It was no surprise that when the former first round pick had few suitors when he became a free agent at the end of the 2006 season.

    All except for one team, the same Philadelphia Phillies who’d thought so highly of him years ago. Maybe they really saw something in Eaton. Maybe they simply wanted to validate the high pick they’d spent on the right hander out of high school. Maybe GM Pat Gillick thought two wrongs somehow made a right.

    Whatever they were thinking, it didn't work.

    Even though the Phillies would win the World Series and qualify for another during the life of Eaton’s contract, the free agent add-on would play a no role. His performance grew too poor to bear, and the team buried him with compensatory moves. After acquiring Joe Blanton the Phillies designated Eaton for assignment midway through the 2008 season and released him prior to 2009.

    Dishonorable Mention: David Bell, Mike Jackson, Gregg Jeffries, Danny Tartabull

Pittsburgh Pirates: Derek Bell

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    Contract: Two years, $9.75 million

    Sad Stats: .173 batting average, 5 HR, one refusal to play

    The Lesson: Don’t mess with Derek Bell’s starting job

    Regardless of the financial fallout caused, and it was considerable, Derek Bell’s deal ranks as the worst free agent contract in Pittsburgh Pirates history because of the theatrics involved. After performing atrociously in the first year of his deal, the veteran Bell reacted poorly to news the following Spring Training that he would have to compete for a starting job.

    Bell refused the gambit and went into what he termed “operation shutdown.” The Pirates released Bell, paying him the remaining $4.5 million to go away, and the outfielder would never play in the major leagues again.

    The real tragedy in all of this is that Derek Bell looked more like an actual Pirate than any player in the team's history. It could have been such a happy marriage.

    And although it wasn’t technically a free agent signing, it should also be noted that in 1999 the Pirates prepared for the opening of PNC Park by signing free-agent-to-be Kevin Young to the richest contract in franchise history. Because nothing screams franchise revival quite like Kevin Young

    Dishonorable Mention: Pete Schourek, Jeromy Burnitz

San Diego Padres: Oscar Gamble

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    Contract: Six years, $2.8 million (1978)

    Sad Stats: One season, 7 HR

    The Lesson: Beware the one-year wonder

    Afro aside, there wasn't much to like about Oscar Gamble's time in San Diego. The previous year, as a member of the Chicago White Sox, Gamble posted career numbers in almost every major offensive category.

    Apparently those high watermarks in average, on-base percentage, home runs and RBI were more a blip than a sign of things to come. Gamble regressed quickly in his lone year in San Diego, dropping a full 200 points in slugging percentage.

    San Diego quickly traded him and his oversized contract to the Texas Rangers and tried to pretend as if the whole thing hadn't happened.

    I guess you could say this was one "Gamble" that didn't pay off...

    ...sorry, I had to do it.

    Dishonorable Mention: Orlando Hudson, Kurt Stillwell, Brian Giles, Greg Maddux, Kevin Jarvis

San Francisco Giants: Barry Zito

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    Contract: Seven years, $126 million

    Sad Stats: ERA over 4.00 every year, did not make 2010 postseason roster

    The Lesson: You can mismanage your way to a championship

    Remarkably, you could argue that three worst free agent signings in San Francisco Giants history all played on the franchise’s only championship team since free agency's inception.

    Apparently the universe likes messing with us.

    Between the rotten deals GM Brian Sabean gave to Barry Zito, Aaron Rowand and Edgar Renteria (also the team’s three highest paid players), Zito’s was easily the worst, a $126 million monstrosity that required not two, not three, but four excellent homegrown pitchers to offset its disastrous consequences.

    The tenuous construction of that team around three mega-deals gone awry ranks as one of the more impressive GM jobs in recent history, almost as impressive as the negligence that caused it.

    Dishonorable Mention: Aaron Rowand, Edgar Renteria, Miguel Tejada, Aubrey Huff (Part II)

Seattle Mariners: Chone Figgins

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    Contract: Four years, $36 million (2010)

    Sad Stats: 50 combined RBI (2010-11), .188/.241/.243 in 2011

    The Lesson: When “Chone” rhymes with “Yawn,” something is amiss.

    Since signing with the Mariners two seasons ago in a deal that was supposed to propel the franchise into contention, Chone Figgins has been one of the worst regular players in baseball. Things bottomed out this year when Figgins quietly, in the shadow of Adam Dunn’s struggles, posted one of the worst offensive seasons in recent history.

    Figgins’s 39 OPS+ was the worst for a batter with more than 250 at bats since Pittsburgh’s Pat Mears equaled the feat in 2000 and his slugging percentage was the worst for a player with that much run since Walt Weiss in 1992. Figgins performed so poorly in 2011 that Seattle reluctantly sat their prized investment in favor of journeyman Adam Kennedy.

    Figgins still has two full years left on his deal with a vesting option for 2014 that goes into effect if Figgins reaches 600 Plate Appearances the year prior. Something tells me he won’t reach that milestone.

    Dishonorable Mention: Richie Sexson, Carlos Silva

St. Louis Cardinals: Danny Jackson

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    Contract: 3 years, $10.8 million (1995)

    Sad Stats: 4-15, 5.78

    The Lesson: Let old lefties lie

    Coming off an All-Star campaign in 1994, the St. Louis Cardinals thought 33-year-old lefty Danny Jackson still had some years left in his well-traveled arm. From there on out, things couldn’t have gone much worse.

    Soon after signing Jackson learned he had thyroid cancer and upon returning lost his first nine decisions as a Cardinal. Before he could fully recover from the first ailment Jackson tweaked his ankle, sapping his confidence and rapidly accelerating his decline.

    Jackson would be the Cardinals highest paid player in 1996 and their second highest in 1997, yet he pitched just 55 innings for the team during those disastrous campaigns.

    Dishonorable Mention: Bryn Smith, Mark Mulder, Juan Encarnacion, Ryan Franklin

Tampa Bay Rays: Greg Vaughn

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    Contract: Four years, $34 million (2000)


    Sad Stats: Never hit 30 HRs, never hit .255, never played 140 games and was gone by the fourth year of the deal

    The Lesson: Unless you're the Marlins, don’t try to build a team through free agency

    The inconceivably large contract awarded to slugger Greg Vaughn typified the Tampa Bay (Devil) Rays’ woes under one-time owner Vince Naimoli. The combustible Naimoli had little time for rebuilding and his thin patience combined with poor decision making in the front office conspired to create some of the worst free agent signings of the late 90s and early 2000s.

    In a list that includes awful deals to Jose Canseco, Juan Guzman and Wilson Alvarez, none was worse than Vaughn’s. I’ll let the New York Times explain:

    “For an expansion team that had pledged to build through vibrant youth, splurging on Vaughn—a 34-year-old, one-dimensional free swinger—made the Tampa Bay front office look downright vertiginous. “

    Eventually a new owner (Stuart Sternberg) and a new GM (Andrew Friedman) blew up the blueprint, recommitted to the farm system and had Tampa Bay in the World Series by 2008. Incidentally, as the Times’ story reports, 2008 was also the first year the Rays no longer had to pay the back-loaded interest owed Vaughn as part of his megadeal.

    Dishonorable Mention: Jose Canseco, Pat Burrell, Juan Guzman, Wilson Alvarez

Texas Rangers: Alex Rodriguez

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    Contract: 10 years, $252 million (2001)

    Sad Stats: Never won more than 73 games during A-Rod’s tenure

    The Lesson: There are 25 people on an MLB roster

    Though the consensus worst contract in Texas Rangers history is that of pitcher Chan Ho Park, no deal in baseball history has singularly destroyed a franchise quite like Alex Rodriguez’s.

    Ten years, $252 million. The terms of the deal are so hauntingly familiar by now that they’ve become something of a boogieman in baseball circles. Never before or after have a group of baseball executives so fundamentally misunderstood the possibilities granted by free agency.

    As should be made clear by the game’s rules, individual players are largely powerless to dictate the outcome of a baseball game. Great batters get four, maybe five, chances to influence a game and if their teammates don’t get on base in front of them or if their pitcher can’t get hitters out, those chances will likely mean nothing.

    Baseball isn’t basketball—one great player can’t elevate a team or even make them competitive.

    In the end, Rodriguez’s contract hamstrung the Rangers so severely that they could not compensate for the things he didn’t do, namely pitching. During A-Rod’s three years in Texas the team never had a starting pitcher with an ERA under 3.84 or an ERA+ greater than 124 (both achieved by Kenny Rogers in 2002).

    The financial disruption caused by Rodriguez’s contract would play a part in forcing owner Tom Hicks to sell the team and declare bankruptcy. The Rangers, still reeling from bad investments, wouldn’t qualify for the playoffs again until 2010.

    No other contract has that sort of wreckage in its wake.

    Dishonorable Mention: Chan Ho Park, Kevin Millwood

Toronto Blue Jays: B.J. Ryan

30 of 31

    Contract: Five years, $47 million (2006)

    Sad Stats: .76 SO:BB ratio in 2009 before being released midyear

    The Lesson: Guys who pitch for one inning aren’t worth $47 million

    Two good years, two bad years, one year where he didn’t play at all and $47 million down the drain. That’s the most succinct summary of B.J. Ryan’s Blue Jays career that I can summon.

    Ryan’s tenure in Toronto started auspiciously. After signing what was then the largest contract for a relief pitcher in baseball history, Ryan made the 2006 All-Star team and finished the year with a sparkling 1.37 ERA.

    In 2007, Ryan underwent Tommy John surgery and never fully recovered. Even a decent 2008 campaign couldn’t mask his rapid decline, and midway through a terrible 2009 the Blue Jays released Ryan with $15 million still remaining on his contract.

    But don’t let the injury mask the obvious question here. Even if he never got hurt, was B.J. Ryan really worth $47 million to a middling Blue Jays team?

    I mean, really...

    Dishonorable Mention: Luis Gomez , Erik Hanson, Mookie Wilson

Washington Nationals: Jayson Werth

31 of 31

    Contract: Seven years, $126 million

    Sad Stats: 97 OPS+, 160 strikeouts

    The Lesson: Fear the beard.

    It may be early, but I’m calling it now: Jayson Werth’s contract will go down as the worst free agent deal in Nationals' history.

    Honestly, it doesn’t feel like a very bold call.

    Even if Werth improves off of his dreadful 2011 performance, he’ll need to surpass any of his prior career levels to justify the $126 million granted him by Nats GM Mike Rizzo. And that’s just in the short term.

    Werth would also need to remain a productive player through his 38th birthday, when the contract ends, to make this deal feel like anything other than a bust. The Nats have a cavalry of young players on the way to help mask this mistake a la Barry Zito in San Francisco, but that won’t make the Werth fiasco any less imprudent.

    Dishonorable Mention: Cristian Guzman, Paul LoDuca, Jason Marquis, Adam LaRoche