From the day Masterson arrived to the Indians in the 2009 Victor Martinez trade, he's always come across as quite a bit different than your average elite athlete. The peaceful and benign nature by which Masterson goes about his business and interacts with others is at odds with his superior size and strength and simply not one we've come to count on from people in his position.
There was a start early in Masterson's Indians career in which he basically got his teeth kicked in. But he didn't spend his postgame interview expressing frustration over pitch selection or execution or a missed opportunity to impress his new bosses. Rather, Masterson bemoaned his role in spoiling an otherwise "beautiful, gorgeous night" at the ballpark for the fans. More recently, he deflected postgame attention away from himself and his latest outing and toward his wife and the cookies she was baking for charity (and Meryl Masterson's cookies are as delicious as they come, for the record).
It should be no surprise, then, that Masterson is going about the sometimes brutal business side of the game in just as genial a manner. Multiple outlets, including MLB.com, have reported that Masterson has expressed to Cleveland a potential willingness to come to terms on a three- or four-year deal that would essentially limit the amount of long-term risk being taken on by the ballclub. The Northeast Ohio Media Group reported a proposal in the range of $40 million to $60 million (depending on the guaranteed years), which, in today's market, seems a reasonable negotiating point for a guy who has ranked among the top 30 in starting pitcher WAR over the last three seasons.
Don't be mistaken. Masterson is no martyr here.
"He's just going to be really rich," said manager Terry Francona, "or really, really rich."
But it's that latter possibility -- one that has to rattle around the brain of guy statistically comparable to newly minted $105 million man Homer Bailey -- that makes this situation so intriguing.
Masterson is, after all, a union rep well-versed in the value of exploring your full worth, not just for yourself but for those who come after you.
"With any good union, they want to try to increase salaries," he said. "That's just by default. But whatever you do, if you're confident and happy with it, so that you're not going to look back in a year and say, 'Man, why did I do this?' you should go for it."
Though nothing was finalized Wednesday, there is an increasing sense here in Indians camp that Masterson and the club just might go for it. To say this would be a score for the Tribe is an understatement, because the organization's need to maximize its player payroll has long been apparent, as has their difficulty in retaining top talent.
That said, there is organizational precedent for this sort of arrangement. Back when he still had dots in his initials, CC Sabathia gave the Indians a hometown deal in an April 2005 extension that guaranteed him just $17.5 million in 2007-08, which otherwise would have served as his first two free-agent years. Sabathia turned down the chance to hit the open market at 26 because of the comfort level he felt as part of the Tribe's core.
"When I got to Spring Training," Sabathia said at the time, "and was around all the guys -- who are more than just my teammates, they're my friends -- I called my agent and said, 'This is where I need to be.'"
The Masterson storylines feels somewhat similar, in that his potentially contentious final round of arbitration-eligibility with Cleveland (the gap between Masterson's request and the Indians' offer was the largest in the league) thawed upon arrival to Arizona.
Of course, Masterson has more collective bargaining agreement wrinkles to keep in mind than Sabathia did. The freeze Draft pick compensation put on the Ervin Santana market has to be considered, as a qualifying offer by the Indians -- combined with the potential free-agent-eligibility of Max Scherzer and James Shields -- could affect his potential price tag. It's certainly worth nothing that a three-year deal signed today would expire after the current CBA expires.
What's amazing about Masterson is that he'll talk about all of this openly, even as the dialogue about his future plays out behind the scenes. This almost never happens, and Masterson probably didn't buy his agent, Randy Rowley, a great deal of negotiating leverage when he freely told reporters he figures "somehow, some way, I'll end up still being here for a few more years."
"He's comfortable in his own skin," Francona said. "I don't see this tearing him up or making him nervous."
Francona, no doubt, is the only reason these extension conversations have had any traction. He was Masterson's first skipper in Boston, and Masterson said Wednesday that this organization didn't truly feel like "home" to him until Tito's arrival a year ago. The long-term deals given to Nick Swisher and Michael Bourn and Michael Brantley have, in Masterson's mind, created a culture in which Cleveland feels more like a destination than a bump in the road.
Masterson has had his own bumps in the road (the 2012 season, notably). His ballpark-adjusted ERA going back to 2011, therefore, is exactly league average. So even if the Indians do retain Masterson on team-friendly terms, it won't necessarily be the bargain that CC's extension proved to be.
But there's no overstating what a lynchpin guy Masterson has become for this organization, what his "everlasting optimism," as rotation mate Corey Kluber put it, has meant in the development of the likes of Kluber and Zach McAllister and Josh Tomlin and Danny Salazar as they've been integrated into the rotation in recent seasons. His teammates talk about his quick return from an oblique injury last September, when he worked out of the bullpen in the final playoff push, with particular reverence.
"I think that's the best kind of leadership you can have," said Tomlin, "a guy who leads by what he does and not what he says."
The things Masterson has said in recent days lead you to believe an extension is likely, if not imminent. Naturally, that could change or otherwise evolve in the coming days. But the public nature of the process, thanks to Masterson's openness about his intentions, has already been unorthodox.
Given the subject, perhaps that shouldn't be a surprise.