Contract Extensions Gone Wrong

With young players becoming more and more prominent throughout the game, teams have begun seeking cost certainty in the form of contract extensions that buy out arbitration and (in some cases) free agent years. Everyone knows about Evan Longoria's sweetheart deal and the tens of millions of dollars the Cardinals saved with Albert Pujols and Boston's bargain contract with Jon Lester, but these contracts don't always work out.

Whether it be injuries, poor performance, or a combination of both, every once in a while one of these deals will turn into a dud. Using our Transactions Tracker, let's look back at some extensions that didn't go as planned…

  • Fernando Tatis (four years, $14MM) – The Cardinals signed Tatis to said deal after his breakout .298/.404/.553, 34 HR, 21 SB season in 1999. It bought out his last pre-arb year and all three arb years, but he hit just .234/.330/.399 in close to 1,200 PA during the life of the deal. St. Louis traded him to Montreal after the 2000 season.
  • Randy Wolf (four years, $22.25MM) – The Phillies bought out all of Wolf's arb years and one year of free agency before the 2003 season, but he gave them just 473 1/3 innings with a 4.43 ERA. He battled elbow trouble and eventually had Tommy John surgery during the contract.
  • Kerry Wood (three years, $32.5MM) – Wood surrendered his last arb year and two free agent years in this contract, but triceps, shoulder, and knee injuries limited him to just 226 innings (3.90 ERA) during the life of the deal, and most of those innings came in 2004.
  • Travis Hafner (four years, $57MM) – Signed the year after his .308/.439/.659, 42 HR season in 2006, Pronk gave up his last year of arb-eligibility and three free agent years. He's battled shoulder issues and hit just .259/.353/.430 since signing. 
  • Jay Gibbons (four years, $21.1MM) – The Orioles bought out Gibbons' last two years of arb and two free agents years after he hit .277/.317/.516 with 26 homers in 2005. He hit just .256/.311/.409 in 179 games during the life of the contract, dealing with knee, groin, and shoulder issues. Baltimore released him just two years into the deal.
  • Jeremy Bonderman (four years, $38MM) – Coming off a strong 2006 season (214 IP, 4.08 ERA), Bonderman signed away his last two arb years and two free agent years. Shoulder injuries hit the next year, and Bonderman pitched to a 5.19 ERA in just 427 IP during the contract.
  • Ian Snell (three years, $8.6MM) – The Pirates secured Snell's three arb years after he posted a 3.76 ERA in 208 IP in 2007, though he's yet to repeat that performance. Snell pitched to a 5.31 ERA in 355 2/3 innings since, and was traded to the Mariners a year after signing the contract.

These are just a select few, but the list goes on and on. The players are trading a shot at a bigger payday for financial security while the team trades risk for cost certainty, but in the end the players are still getting their millions while the clubs could be left with nothing to show for their investment.


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39 Responses to Contract Extensions Gone Wrong Leave a Reply

  1. Ian Snell, for 8.6 M over 3 years isn’t exactly breaking the bank.

  2. YaGottaBelieve11 4 years ago

    Oliver Perez 3/36 and Luis Castillo 4/24 don’t make this list over Ian snell?

    • YaGottaBelieve11 4 years ago

      missed the “buying out arb years” part. Thats what i get for just reading the headline and the players

  3. YaGottaBelieve11 4 years ago

    Oliver Perez 3/36 and Luis Castillo 4/24 don’t make this list over Ian snell?

  4. rathman53 4 years ago

    Eric Chavez would be a nice addition to this list.

  5. brewcrew262 4 years ago

    how could you not put the brewers and jeff suppan? 4years, 42 million. he got worse every year

    • He wasn’t an extension, he was a free agent signing. They weren’t buying out free agent years or locking up price certainty on his arb years.

  6. Here are some more, all for one team:

    Dontrelle Willis, 3 years, $ 29 million. The worst starting pitcher in the National League didn’t get any better after being traded with Miguel Cabrera. Go figure.

    Carlos Guillen, 4 years, $ 48 million. Just one year and $ 13 million to go. Guillen led the league in errors by a shortstop the following season, and was moved to left field, to third base, and now second base, but spent more time on the DL than on the field.

    Nate Robertson, three years, $ 21 million. The Tigers paid off the final year of his contract to go play for a few other National League teams.

    Magglio Ordonez, $ 18 million option vested. Half the season on the DL in 2010, but extended again for another $ 10 million. Funny thing is, most fans like this extension.
    Pudge Rodriguez, $ 13 million option picked up, and his performance promptly tanked, being unloaded to the Yankees for Kyle Farnsworth in the latter half of the 2008 season. Good contract, bad option year.

    Todd Jones, one year, $ 7 million extension. From closer, to bench, to DL. The contract was good, but the extension wasn’t.

    Kenny Rogers, one year, $ 8 million extension. Again, missed half the extension year on the DL after thoracic outlet surgery. Good contract, bad extension.

    Dmitri Young, $ 8 million option vested, and he begged off injured the following week. Following season, beat up his girlfriend, didn’t show up for court, was a cancer in the clubhouse, didn’t perform, was released, and of course blamed it all on the team for not supporting him.

    Adam Everett, $ 1.55 million extension. Bad contract and bad extension, both signed because Dombrowski shot the wad on so many other bad extensions. Everett was released in May of 2010.

    Pretty much every contract extension that Dave Dombrowski signed, or every option he picked up blew up in his face. The notable exception was Placido Polanco’s four year extension at just 4.6 mil per season. He made up for that by failing to offer arbitration when Polanco walked and went back to the Phillies, forefeiting two first round picks by that failure.

    Thankfully, all but Guillen’s extension are done. Let’s hope that the extensions for Verlander and Cabrera turn out a bit better!

  7. stl_cards16 4 years ago

    Apparently Mike, you should have added the definition of EXTENSION to the post. Some here, obviously do not grasp the concept.

  8. Eric Hinske with the Blue Jays was another one….

  9. Cardsfan387 4 years ago

    How is Kyle Lohse’s 4 year/$41mil contract extension not on this list?

    • Ferrariman 4 years ago

      because he was a free agent. All the ones he listed were guys who were arb-eligible who signed extensions during the team control process.

  10. Verlander_Will_Save_Us_All 4 years ago

    Every Tigers extension since 2006 excluding Cabrera can go on the list…. every freaking one.

    • Pawsdeep 4 years ago

      Cabrera was a fair deal and so was verlanders….but aside from those two I agree with you.

    • mrsjohnmiltonrocks 4 years ago

      I already declared the Tigers the WINNERS!

  11. Ferrariman 4 years ago

    i can’t believe my comment wasn’t approved yet. Its not like i had something dirty wtf…never again am i gonna use a link.

    anyways, here is an exert from an article on stlsports from back in the day. The tatis signing was a blessing in disguise!

    “According to Cardinals manager Tony LaRussa, the organization was faced with the dilemma of trading either Tatis or the fast-rising Pujols at some point. Tatis’ lack of desire and personal discipline after inking his multi-year contract this past spring apparently made the decision easier for them to make. When the Expos presented them with the opportunity to gain a starting pitcher and a lefthanded reliever, he was shipped to the Great White North.”

    Thank you Tatis for having a lack of desire!

  12. ryanszabo 4 years ago

    why dont you guys include OPS? That’s probably a better indicator of the player’s effectiveness than avg/obp/slugging.

    • thegrayrace 4 years ago

      I think most of us can add two numbers with relative ease. 😉

  13. 5_tool_MiLB_fool 4 years ago

    I can’t believe that Bonderman who was always such a crap pitcher to begin with got a contract like that. That is the only contract for a pitcher that can be worse than aaron cook’s 9 mil a year

    • The one given to willis was pretty bad.

      • 5_tool_MiLB_fool 4 years ago

        yeah but bonderman was not even close as good as willis was when he received his contract. bonderman has always been a bad pitcher, willis had a few ace seasons before he got that contratc; then he turned to crap

  14. woadude 4 years ago

    Remember Bret Boone? now that was a roider.

  15. DykstraInvestments 4 years ago

    Kyle Lohse and Mark Mulder (with the Dan Haren loss) are hard to swallow but I think it was more bad luck than anything…

  16. i too miss the days he was on roids

  17. ykw 4 years ago

    In fairness, his numbers the last four years are heavily weighted down by the year he tried to play through the worst of the shoulder woes:

    2007: .266/.837/120
    2008: .197/.628/69
    2009: .272/.826/120
    2010: .278/.824/131

    Pronk isn’t as crazy-good a bat now as he was half a decade back, but he’s not quite as far from the rest of the league as a comparison of his raw numbers might initially lead you to believe.

  18. your argument is invalid

    he has every symptom of a steroid user

  19. TapDancingTeddy 4 years ago

    I think it’s really unfair to label Hafner a roider without any evidence. It seems every big hitter who has a steep decline is labeled that way, while pitchers, and position players who don’t hit homers can have any career arc without suspicion.

    Hafner has had injuries which account for his decline. So, by the way, has Grady Sizemore, who you could call “juicer” on based on the same non-evidence.

  20. say you are correct, then who are other monster-performance players who went on to sign monster contracts then decline the remainder of their career due to “shoulder injury”

    weird huh?

  21. ykw 4 years ago

    Which “steroid user[s]” have a history of their offense dropping from great to just pretty darned good (twenty-to-thirty per cent above league average), with the exception of a single Ivan DeJesusian season shortened by major surgery?

  22. “Steroid user” blah blah blah blah blah. What symptoms would those be Tony? Will you be using science or speculation on this one? Fact or heresay? Barry Bonds or Roger Maris? Your hand has been called.

  23. stl_cards16 4 years ago

    The days of accusing every player that had a sharp drop in production of using steroids are gone. Welcome to today, no one wants to hear about it anymore.

  24. The_Silver_Stacker 4 years ago

    We don’t know for sure, but the guy is still HUGE he must be about 250lbs and looks jacked.

  25. This is by far, one of the best posts on this board

  26. 5_tool_MiLB_fool 4 years ago

    yeah he basically looks like a jim thome except all in muscle. Im going to ignore the argument going on here but I’ll say he was on steroids, but i doubt he is on anything now.

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