Masterson Extension Offer a Lucky Miss One Year Later

There’s an old adage, “some of the best trades are the ones that are never made.”

It’s probably even more truer in free agency and the Indians are no better example. Two years ago the Tribe surprised its fan base and much of baseball when it spent an uncharacteristic $112 million on free agents Nick Swisher, Michael Bourn, Brett Myers and Mark Reynolds. Almost immediately it was obvious that Myers was a bad decision, and after a storm of homers in the first six weeks, Reynolds too was let go before 2013 ended.

A winter ago, the Indians were much more quiet, signing David Murphy and John Axford. Each were supposed to be veteran presence, lightening the load and pressure on the younger players around them. Instead, Axford was replaced as closer by Cody Allen after six weeks and Murphy had his second straight disappointing season. Mistakes in free agency can be costly and it has cost the Tribe in excess of $130 million over the last two winters. It’s no wonder the Indians have not been linked to any free agents this winter, not to mention the roster is full of players under team control for the foreseeable future.

But the Indians dodged a major bullet when Justin Masterson chose not to accept their three-year, $45 million contract extension. Masterson was fresh off a strong 2013 and drawing comparisons to Homer Bailey, who had just inked a six-year, $105 million deal in Cincinnati. Masterson wanted a two or three year deal, but at an average yearly salary of around $18 million per season. At the time, it seemed like money the Indians should spend. In hindsight, they knew their roster very well.

Masterson went on to struggle mightily in 2014, going 4-6 in 19 starts with a 5.51 ERA for the Indians, complete with a trip to the disabled list, before being dealt to the St. Louis Cardinals at the trade deadline. Masterson shares as much responsibility as any player for the Tribe’s Unfinished Business ending in Royal Disappointment. When Masterson finally left the rotation and roster, it opened the door for starters T.J. House, Danny Salazar and Carlos Carrasco to assume a larger role and each thrived with the opportunity.

Had the Indians committed long term money to Masterson last spring, the organization would have been left with no choice but to stick with their large, side-winding hurler instead of focusing on a youth movement. Masterson’s mechanics have always been very technical and the slightest change seems to be the difference between dominance and disappointment. It only got worse for Masterson in St. Louis, when instead of being the pitcher they needed for postseason, he was jettisoned to the bullpen and left off the playoff roster. His ERA ballooned to 7.04 during his time in St. Louis.

Masterson cost himself millions when he turned down the Indians’ offer last spring, but rebounded to sign a one-year, $9.5 million deal with the Boston Red Sox last week. We should all be so lucky to be punished like Masterson after the worst year of our career. Masterson is supposed to be used as a starting pitcher, and if he succeeds, will stand to recoup most or all of the money he walked away from.

However, it’s the Indians who dodged a major bullet and may have saved the direction of the franchise. Had the Indians and Masterson inked a deal together, the 2015 payroll would likely have over 50% of its money wrapped up in he, Swisher and Bourn. The money used to extend Masterson was instead used to extend Michael Brantley, Yan Gomes and Jason Kipnis. Instead of a core of three players in their 30s—each with injuries in 2014—the Indians have a group in their 20s. Brantley was an MVP candidate, who has got better each year. Gomes shined as the Tribe’s backstop after a poor first six weeks, defensively.

Boston, and their much larger payroll, can afford to gamble on Masterson. If Masterson struggles again, he’ll go by the wayside and Boston will eat the salary like so many other bad free agent deals. But, had Cleveland made that mistake last spring, the ramifications would have been much more crippling to the $85 million payroll of the Tribe.

Some of the best contracts are the ones never accepted.

Photo: Getty Images

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