I will be very disappointed if they don't sign Masterson. The biggest risk with signing pitchers to big money deals is contract length, and he's willing to alleviate that worry by signing a three or four year deal. There's several factors that have to be considered here:
1. He's Very Good Is he Clayton Kershaw? Certainly not, but who is? He's going to give you 200 IP, which is especially important with the rest of the staff being so young. According to Matthew Berry, Masterson allowed a well-hit average of .120 last season, third-best among qualified starters. Masterson also had a higher percentage of opponent plate appearances end in strikeouts (24.3 percent) than Justin Verlander (23.5 percent). At age 28, the Indians would be getting his prime years. He's going to lead by example, another valuable characteristic for guys like Danny Salazar. He's also very close to Tito, and I'd think we want to keep Tito happy.
2. The Market - Masterson could easily get more money on the open market next year. He'll likely be the 1st or 2nd best SP available and could command big-time dollars. Simply put - nobody as good as him is going to give Cleveland a discount. You have to jump at the opportunity.
3) The Core - Michael Brantley, Jason Kipnis, Nick Swisher, Carlos Santana, Michael Bourn, Lonnie Chisenhall, and Bryan Shaw are all under team control through 2017. Danny Salazar, Corey Kluber, Zack McCallister, Vinnie Pestano, Cody Allen, Trevor Bauer, Carlos Carrasco, and Yan Gomes are under team control beyond that. Signing Masterson to a three or four year extension means the Indians would have their entire core in place through at least 2017. How many teams coming off of a playoff appearance can say that?
4) The Fans - For the first time in a long time, the Indians have the fans' attention. The Cavs are still struggling, the Browns are always struggling, and this city is desperately searching for a sports team to love. The Indians could be that. First and most importantly, they're a damn good team. Second, they are a fun team to follow with plenty of fan-favorites. It would be a major move for the front office to show they are seriously committed to bringing a World Series to Cleveland by letting the same fans who watched C.C. Sabathia and Cliff Lee walk away in consecutive years see the team lock up their top starter. I'm not a "Discount Dolan" type and I rarely bash the Indians when players walk - usually the contracts aren't worth the risk. But this is a unique situation, and signing Masterson is absolutely worth it. For a fan base afraid to buy jerseys with names on the back of them, being able to show them you're going to put a good product on the field for at least the next four seasons could go a long way for this franchise and its support from the fans of Cleveland.