MLB: Chicago White Sox at Cleveland Indians

Public negotiations are never easy. What somebody says to the media (or to “sources”) isn’t always a fair representation of what really happens at the negotiating table. Players swear up and down that family considerations hold equal weight when planning their future but, as we’re told over and over, it’s all about the money.

Justin Masterson is set to become a free agent at the end of the season. Earlier this winter, it appeared inevitable that the big righty would work out a deal with Cleveland. Masterson joined the Indians in 2009 and has four up-and-down seasons under his belt. Masterson’s public comments suggested he wanted to stay in Cleveland and was willing to take a shorter deal to facilitate it.

But as of yesterday, negotiations between the two camps broke off and it appears Masterson will become an increasingly rare bird – the year-by-year player who shops himself to the highest bidder as a true free agent.

For pitchers, the prices are what the prices are. When Masterson modestly suggests a shorter term deal worth around $17 million per year, it seems fine. Fair, even. The going rate is the going rate – this is less than what Homer Bailey got from the Reds, as Ken Rosenthal points out. But the Tribe do not carry a large payroll, and giving $17MM to one pitcher represents a significant portion of their overall payroll.

Does Justin Masterson deserve to enter that particular strata of pitchers? In two of the last three years, Masterson pitched like a number two starter, posting close to 4 Wins Above Replacement in 2011 and 2013. But in 2012 (and 2010 as well), Masterson struggled. The long ball plagued him slightly and his ERA climbed north of 4.00, even if his supporting numbers suggested he wasn’t so bad.

2013 saw his strikeout rate soar to nearly 25%, well above his career mark around 18% to that point. Much of his success in 2013 comes from improving his results against left-handed batters. As a predominantly two-pitch pitcher, getting lefties out is always the toughest task for Masterson. Last season, he threw his slider much more regularly against lefties than in previous seasons. Using that pitch as a weapon against lefties just sets up his big fastball/sinker, still his best pitch.

There is a risk of overanalyzing Justin Masterson, as he is more of a feel pitcher than most guys in the big leagues today. He is a pitcher who doesn’t exactly tinker on the mound but one that works with his catcher to try and find his best release point in real time. It is more art than science as he feels his way into his sinker/slider on a given day.

Working with his catcher, Masterson likes “reading” batters to see what pitches they’re keying on and make adjustments. Beyond adjusting to what hitters do, any starter with so much movement in all (both) his pitches relies on what works on a given day.

What does this mean for his future? Perhaps Cleveland isn’t quite comfortable going longer term coming off a career-best season. Or maybe Cleveland is just happy to let the big righty finish this year and then ride into the sunset, leaving only a compensatory draft pick in his wake. Chris Antonetti and his merry band of quants would much rather find the next bargain than pay big bucks for a starter entering his 30s.

When Masterson takes the ball for the Tribe on Opening Day for the third straight year, it could well be his last. Should Cleveland falter this season, the free-agent-to-be is sure to hear his name in countless trade rumors. Even if Cleveland isn’t willing to commit to Masterson long term (owing to a lack of funds or a lack of faith), some team will happily give the big, durable ground ball machine more than the three years he sought from his current club.

When it comes to writing $60 million checks, nothing is ever easy. No matter how open to a shorter, cheaper deal Justin Masterson and his agency appear, there is always more than meets the eye. Unless Cleveland has draft pick compensation in its mind and moving on from their current ace has been the plan all along. When one party will only deal in an extreme value situation, there isn’t really a negotiation at all, is there?