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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