Earlier today, Justin Masterson told reporters that he believes that "somehow, some way" he'll be in Cleveland for a few more years after this one. That statement can serve as a beacon of optimism for Masterson/Indians fans, but there have been plenty of instances of a player going on record to say he thinks he will/wants to/hopes to stay with a team, only to sign elsewhere in the future.
Masterson isn't likely to give the Indians a hefty discount with just seven to eight months sitting between him and free agency, and the price for extending players has seemed to trend upward recently. Masterson is one year older than fellow right-hander Homer Bailey, who signed a six-year, $105MM extension with a comparable amount of service time. The similarities don't stop there, either. As that comparison shows, fWAR assigns Masterson the higher value due to his higher innings total, but in terms of ERA, FIP and xFIP, the two have accumulate very, very similar results over the past three seasons. Masterson relies more on ground-balls, while Bailey's leaned more heavily on superior command and a few more whiffs.
Regardless, Bailey signed away five free agent seasons for roughly $95MM. That figure, as noted by Paul Hoynes of the Cleveland Plain Dealer in an updated piece on Masterson's comments, simply isn't going to be on the table from the Indians.
Masterson currently faces a decision: he's experienced his ups and downs in recent seasons (2010 and 2012 were not pretty), but he's a talented pitcher in the midst of his prime who is months away from being one of the best pitchers on the free agent market alongside James Shields, Max Scherzer and Jon Lester (Lester, of course, is widely expected to sign an extension this spring). Another strong season would give Masterson three years of an ERA well under 4.00 with 193-plus innings and one of the league's best ground-ball rates. However, his comments today also hinted that he'd like to stay in Cleveland, and an extension would eliminate the risk of a poor season or injury sapping his potential earnings.
It would be beneficial to the Indians' long-term outlook to keep Masterson around and pair him with the likes of Danny Salazar for years to come, but the team could also look to fill the void internally (or with cheaper free agent/trade options) and recoup a draft pick via qualifying offer next offseason in letting Masterson walk.