MLB Free Agency: Ranking Jonathan Papelbon Amid 30 Most Moronic Contracts Ever

Matt TruebloodSenior Analyst IJune 22, 2016

MLB Free Agency: Ranking Jonathan Papelbon Amid 30 Most Moronic Contracts Ever

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    Jonathan Papelbon got $50 million over four years from the Philadelphia Phillies last month. That's a ridiculously awful decision, regardless of its outcome.

    Ruben Amaro was an idiot to commit to that deal.

    Too often, general managers get a bad rap for contract commitments that made decent sense at the time, but turned out poorly. On the other hand, many are lauded for contracts that were stupid, but turned out better than could have been hoped. 

    Results-based analysis is a poor way to measure a contract. We need to examine the information that was available to the executives who signed big contracts, and decide whether they had any decent basis for pulling those triggers.

    Here are 30 instances from the annals of MLB where a manager had utterly no justification for his actions.

30. Jarrod Washburn

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    Jarrod Washburn was not a good pitcher at any point in his big-league career. At his very shining best, he was average, and by the time he became a free agent after the 2005 season, even those days were far behind him.

    Unfortunately, the Seattle Mariners didn't get it. All they saw in Washburn was an extreme fly-ball pitcher—one they felt would fit neatly to their cavernous home park.

    They committed over $9 million per year to Washburn on a four-year deal, and got what they should have expected. Opponents ripped a whole lot of doubles and triples off Washburn, and despite the park, they hit their share of homers, too. 

    Washburn never missed bats. He never had elite control. A terrific strand rate—he left 15 percent more base-runners on the paths than the average pitcher in 2005—conjured up a 3.20 ERA for Washburn in 2005, which hooked Seattle. They paid for it with ERA figures of 4.67, 4.32 and 4.69 in Washburn's three full seasons on the team.

29. Alfonso Soriano

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    Soriano did hit 46 home runs and 41 doubles and stole 41 bases for the Washington Nationals in 2006. That provided plenty of incentive for the Cubs to spring on him that winter.

    The red flags, though, were everywhere. Soriano had been forced out to left field for the 2006 season—not a valuable defensive position. He also struck out in 22 percent of his plate appearances, a substantial step in the wrong direction from where he had been the three previous seasons.

    Cubs GM Jim Hendry likely soothed himself about that by noting Soriano's 9.2 percent walk rate, a career high. But Soriano drew 16 intentional walks, covering a large portion of the difference between his 2006 walk rate and his standard.

    It was a deal that ignored lurking risk factors just below the surface, but it wasn't as bad a decision as many think. It's worked out about the way one ought to have expected it to work out: Soriano has averaged 3.1 WAR per season in Chicago, according to FanGraphs.

    It's a bad contract and a worse decision, but given to a good player.

28. Carlos Silva

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    Silva had a career strikeout rate of fewer than four per nine innings through the 2006 season, when the Mariners (here they are again) paid him huge money. They were looking at better skills (Silva has great control and is a ground-ball guy) than they were when they inked Washburn, so they gave Silva more money: $48 million over four years.

    Silva promptly imploded. He still couldn't miss bats, and on top of that, he got even fatter (he was always fat) and began breaking down physically.

    It's important to distinguish between fat for a reason and fat for the sake of fat, and the Mariners failed to do so.

27. Bartolo Colon

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    Call it Silva Syndrome, though Colon signed first. Colon Syndrome might be mistaken for something else.

    Again, the mistake stems from the inability to tell when fat pitchers are at risk for major regression or injury. CC Sabathia is a humongous man, but he's not a bad-body pitcher. He wears his weight naturally. His size works in his favor on the question of durability.

    Not so for Colon and Silva. That's how they got grossly overpaid.

26. Carl Pavano

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    Assuming Pavano's modest two-year success would translate straight from Florida to Yankee Stadium was wrong. Betting $40 million on it was just dumb.

    Pavano was a narrowly above-average pitcher with an injury history, whom the Yankees paid like a slightly better pitcher who presented no risk. The tepid stuff he had all along should have been a red flag.

    No such luck.

25. Todd Hundley

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    In the 11 seasons Hundley played prior to signing for hefty money over four years with the Chicago Cubs in 2001, he had three good ones. Of the three before the contract, two were disastrous.

    In the winter prior to the 2000 season, he was on the very edge of the baseball world. A year later, he got $27.5 million.

    One major reason the Cubs signed Hundley was nostalgia, or something like it. Nepotism might not even be too strong a word. Those are always bad reasons to make actuarial choices about free agents, and this one backfired the way it deserved to.

24. Kei Igawa

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    The free-agent market often fractures into quartiles. Smart spenders know that there are great values to be had in three of those four areas.

    The one to avoid is always the second. Elite players are occasionally overpaid, but the money rarely matters as much as the big value they return by producing well. The third and fourth are veritable bargain bins, where even a miss doesn't hurt much and a hit can make a positive impact.

    Igawa was in the second tier. Failing to match the Red Sox in their commitment to Daisuke Matsuzaka, the Yankees settled for Igawa, and ended up paying $46 million for a pitcher who was worth perhaps half that.

23. Adam Dunn

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    The moral of this story is clear: If you're going to pay a player $56 million, you had better have a defensive position in mind. Dunn's bat disappeared in 2011; it should bounce back.

    Since he is a DH-only player, though, absolutely everything rides on that iffy proposition. 

    Dunn was a risk even from an offensive perspective. It's often an early warning sign of impending decline when an historically hyper-patient hitter gets more aggressive at the plate—as Dunn did in 2009-10.

    Often, that player is cheating for power, and while it may work for a few years, such an approach nearly always results in collapsing production when the bat slows down.

22. Denny Neagle

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    This one was an early lesson on a central tenet of the new sabermetric baseball order. Any player can be a good (or bad) signing, so long as he fits well to the needs and environment of the team signing him, and so long as the money was right.

    By the time the Rockies handed Denny Neagle $51 million, he had been past his prime for five years, was ill-suited to a mid-rotation workload and had demonstrated extreme fly-ball tendencies.

    All of that makes for a terrible mix in Coors Field, yet the Rockies gave Neagle ridiculous money.

21. Carlos Zambrano

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    Jim Hendry should have known Carlos Zambrano was an abused hurler; he'd overseen the abuse. Hendry had hand-picked the man (Dusty Baker) who ran Zambrano thoroughly ragged at ages 22, 23, 24 and 25. He knew the right-hander had problems with cramping, fatigue and dropping velocity, not to mention command.

    Hendry folded to public pressure in signing Zambrano for $91.5 million. He did it before Zambrano could even get to the free-agent market, where the good bet is that the market would have set a lower price point.

    Negotiating against oneself is always a bad move.

20. Greg Vaughn

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    Vaughn was 34 years old when the Rays signed him prior to the 2000 season. A one-year deal would still have been a great move. He could still hit, after all. A two-year deal might still have been a plus. A three-year deal, though, would have pushed the boundaries of viability.

    A back-loaded four-year deal? Forget it.

    That's what the Rays did. They paid to watch Vaughn slug his first season, fade his second, flop hideously in his third and play out the final year in Colorado.

    He was too one-dimensional to pay through age 38, but the Rays did it anyway.

19. Mike Hampton

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    This is a case of poor decision-making, but it turned out even worse than it probably deserved to. Consistently cited as one of the worst deals ever, it really represented an aggressive play to grab the best pitcher on the free-agent market.

    The only problem was that Hampton, like Neagle, relied on fly balls to get outs, and since the Rockies had a fairly uninspiring defensive outfield at that time, a lot of those fly balls—even those that stayed in the park—ended up as hits.

18. Mo Vaughn

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    Vaughn's fatness did not ruin the six-year, $80 million deal the Angels gave him. It was ruined before the ink was dry.

    Vaughn relied on bat speed to be a great hitter. He also relied on the proximity of the left-field wall in Boston. He walked fairly often—largely as a result of pitchers being nervous around him—and he struck out a bit more than the average slugger.

    At 31, he moved to Anaheim, a pitcher-friendly park. He lost a tick of the bat speed, which led pitchers to throw more strikes. He walked less, struck out more and his power diminished substantially. Vaughn had no defensive value and was a clogger of the base paths, at least until he began to get injured. At that point, he could no longer reach base frequently enough to clog them.

    This was simply a move the Angels did not think through far enough.

17. B.J. Ryan

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    It sometimes feels like every stat-savvy fan everywhere could shout from the mountaintops at once, and GMs still would not hear us: Stop giving relief pitchers mega-deals!

    B.J. Ryan was a left-handed pitcher with a middling fastball and a plus slider who had had two good seasons when he hit free agency. Relievers generally have three good seasons.

    Someone should have given him a hefty one-year deal and been done with it.

    Instead, the Blue Jays signed Ryan to a huge multi-year deal. He had a terrific year, then three abysmal years, then floated out of baseball. That's life for heavily used relief pitchers. 

16. Jayson Werth

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    This move could have been worse. Don't laugh, it could have been.

    Many believed in the aftermath of the Werth signing last December, that the Nationals were merely trying to make a statement. They paid him $126 million over seven years, a massive overpay for a man with a very limited sample of playing time from which to draw conclusions about his value.

    It was the worse because he will never play anything more valuable than a corner outfield spot.

    That's all bad news. The good news: statement made. And the Nats got Werth. Apparently, they made this move just to show they can land big free agents, so at least they didn't decide to state that by giving Adam Dunn $126 million.

15. Jeff Suppan

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    Suppan was another pull from that second-quartile bin. The Brewers felt he was worth four years and $40 million, and given the ridiculous free-agent climate that offseason presented, maybe they were right.

    By that rationale, though, they should rather have signed Ted Lilly (who got the same deal from the rival Cubs) for about $50 million over four seasons.

    You don't find undervalued assets at Macy's or Bloomingdale's. The Brewers learned that the hard way.

14. Chone Figgins

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    Figgins had a terrific season the year before signing on with Seattle. He led the American League in walks and was a sparkling defensive third baseman.

    But there were hidden problems. Figgins has no power, so the walk rate was unsustainable. Plopped into an anemic offense, Figgins presented no risk to opposing pitchers and they quickly learned to simply knock the bat out of his hands. Furthermore, Jack Zduriencik seemed to have decided Figgins was a defensive star based solely on a single season of advanced defensive metrics.

    That's better than going by fielding percentage, but it leaves out critical questions. Figgins never had the physicality to play the position ideally, and he had help on the Angels infield. 

    Quickly, the Mariners flipped Figgins to second base, which only aggravated the problems with his glove. Two years into the contract, it's an albatross.

13. Juan Pierre

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    Ned Colletti is a terrible GM. This is a theme in my recent work; I don't deny it, but embrace it.

    He signed Pierre for five years and $44 million prior to the 2007 season. Pierre was already well into the act of proving himself unfit for center field, feeble on his throws, unable to draw walks and unable to hit for power.

    He was, at best, a fast seventh hitter with good range in a corner outfield spot. That never should have been worth what the Dodgers paid. Colletti, though, is a terrible GM.

12. Andruw Jones

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    Ned Colletti is a terrible GM.

    The market for Andruw Jones in the winter of 2007-08 was unpredictable and uneven. Some teams half-believed he could regain the form that once made him an elite center fielder. Most did not. None thought he still was that man, except apparently Colletti.

    He gave Jones a two-year, $36.2 million contract. This to a man whose defensive value had disappeared, who could not make contact consistently and was allergic to walks.

11. Manny Ramirez

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    Ned Colletti is a terrible GM.

    At some point in the winter of 2008-09, he was bidding against himself for the services of Manny Ramirez. He could probably have had him for $30 million over two years. He certainly could have had him for $35 million.

    Instead, Colletti let Ramirez push him to $45 million, apparently just for the right to brand jerseys with the words "Mannywood."

10. Jason Schmidt

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    Ned Colletti is a terrible GM.

    If you're going to pay for a pitcher's age-34 to age-37 seasons, that guy had better be from the top quartile of the market. He had better be a true star—not three years removed from contending for a Cy Young award, but contending for one right then.

    Colletti poured $46 million into Schmidt in the hopes of getting some kind of magic revival from the right-handed hurler. None came.

9. Derek Jeter

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    Is Jeter worth more to the Yankees than to any other club? Sure. He might even be worth something close to the $51 million they committed to him last winter, at least in terms of money.

    Fans love him in New York. He is bigger than the game.

    But the deal costs New York on the field. Making decisions based on fan appeal and emotional attachment to the franchise nearly always hurts the on-field product.

    The Yankees should have been high bidders for Jose Reyes or Jimmy Rollins this winter. Instead, they'll pay big bucks to watch Jeter's twilight years.

8. Ryan Howard

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    This deal is only just preparing to start, but Howard might not even play the first game included therein. At $25 million per year, that stings. 

    Injury aside, though, the team overpaid its slugger when he was yet a year and a half away from free agency.

    Howard is a mediocre defender, a bad base-runner and a strikeout-prone slugger. He draws walks, but not disproportionately to his power, which has quietly diminished a bit the past two seasons.

    This is a simple case of a team getting too excited about home runs and RBI and ignoring more important numbers.

7. Gary Matthews, Jr.

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    Before signing with the Angels for five years and $55 million, Gary Matthews, Jr. had spent only one season as a productive regular. He lacked his father's pitch-recognition and plate-discipline skills, so he had little value on offense and his athleticism could carry him only so far.

    The Angels seemingly got so enthralled by his tremendous tools that they forgot he was already on the wrong side of 30, and therefore unlikely to suddenly learn how to play baseball.

6. Alex Rodriguez

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    Four years into a 10-year deal, this looks bad. That's a sign that an error in judgment was made.

    The spectacle of Rodriguez opting out after an MVP season in 2007 was gripping, but mostly for the simple reason that the Yankees were negotiating so boldly with themselves. Other teams made calls and offers, but all along, the Yankees were the only real suitor for Rodriguez.

    Why they ended up paying him $275 million for 10 years is an open question.

    The best answer? Because it's what he asked for.

5. Gil Meche

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    This is another classic second-quartile pitching signing, with a couple fascinating extra layers of stupidity mixed in:

    1. The Royals paid Meche, a comparable pitcher to Jeff Suppan, $15 million over one more season than Suppan got.
    2. Meche had a 4.65 ERA at the time of the signing.
    3. The Royals were terrible, would have been terrible even if Meche became an ace, and thus had no good reason to pay such a premium to acquire him.

4. Rafael Soriano

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    Soriano hung in free-agent limbo for a long time last winter, looking for the most money he could get, regardless of role.

    The Yankees were a team Soriano targeted, because of course, they had money. They always do. What the Yankees didn't have, though, was a good reason to pay Soriano to pitch the seventh inning.

    Recognizing as much, GM Brian Cashman advocated for other uses for the team's money. He was overruled, and the head honchos in the Bronx strong-armed him into a three-year, $35 million deal with Soriano.

    Forget the axiom of relief pitcher mega-deals: Isn't it a bad idea to make a deal this fractious for your own organization?

3. Barry Zito

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    Brian Sabean made the same mistake Ned Colletti made with Jason Schmidt in the same winter Colletti made it—only he made it at three times the investment. Zito had actually won a Cy Young award, after all, so the fact that it had been four years ago weighed not at all on Sabean.

    Neither, apparently, did Zito's high-volume, medium-quality trio of seasons to close his Oakland tenure. He probably feels it now.

2. Jonathan Papelbon

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    Papelbon has never pitched 70 innings in a season as a professional baseball player. Never.

    This is the man the Phillies just signed for four years and $50 million, with a (very reachable) fifth-year option.

    It's not that Papelbon is bad. It's that, being a relief pitcher, he could go bad fast. In the meantime, he's giving you very little value by volume with which to cushion a possible fall-off in skills.

1. Vernon Wells

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    Vernon Wells was still a year from free agency in December of 2006 when the Blue Jays showered him with $126 million over the next seven seasons. He would not have gotten that much even on the open market.

    He was a player who did not walk much, whose defense was overrated and whose value depended on his power and contact skills. Those eroded quickly, and made the deal look terrible.

    Then again, it was.