Nine-figure contracts are becoming more commonplace in baseball and yet teams still can't buy certainty, no matter how large the investment. For every Derek Jeter, Manny Ramirez or Albert Pujols (on his original seven-year, $100MM deal with St. Louis) who more than lived up their contracts, there's a Mike Hampton, Vernon Wells or Johan Santana whose huge salaries became an albatross on their teams' payroll.
This offseason saw five new members join the $100MM club…
- Zack Greinke signed the offseason's biggest free agent contract, a six-year, $147MM deal with the Dodgers.
- Despite some concerns about his age, injury history and off-the-field issues, Josh Hamilton received a five-year, $125MM contract from the Angels.
- The Mets kept their captain in the fold by signing David Wright to a seven-year, $122MM extension.
- More surprisingly, the Rays similarly locked up their franchise third baseman by exercising their last three option years on Evan Longoria's contract and adding six more years to the deal, making it a total of nine years and $136MM.
- Felix Hernandez signed the largest contract ever given to a pitcher, agreeing to a seven-year, $175MM extension with the Mariners.
It's an intriguing collection of both pitchers and position players of different ages and stages of their career. It's also quite the mix of win-now and semi-rebuilding teams in big, medium and small markets taking the risk on these massive contracts. It's also fair to say that even if a player doesn't live up his salary over the entire length (or even a year or two) of a $100MM+ contract, a team might still consider it a good investment if they win a World Series or two over the course of the deal — call it the Barry Zito loophole. It's hard to look five or ten years into the future but all things considered, which of these five deals stands the best chance of being looked back on as a "win" by the team in question?