The Red Sox have just begun the first mile on a long road to a title defense. The 2013 World Champions are entering the 2014 campaign with a club that is essentially the same as last year’s but with many unanswered questions about the future. Tony Massarotti might, more than anyone else in Boston, have some of those answers. The former Boston Globe columnist and current co-host of Felger and Massorotti on 98.5 The Sports Hub is widely regarded as one of the brightest baseball minds in Boston, and the Mass Media recently spoke with him about some of the conundrums that are on the minds of Red Sox Nation members.
Right now, the talk of the town in Ft. Myers is David Ortiz. The 38-year-old DH has made it clear that he wants another year on his deal, which has stirred up a debate amongst members of the media who are extremely loyal to Ortiz and those that believe that he should play out the remainder of his current deal before he asks for another one.
Massarotti said, “Ortiz is certainly entitled to ask for the contract. I just feel like this has become an annual issue, and the Red Sox addressed that last year with the idea that they would address it again at the end of 2014.” He added, “it’s nothing personal, it’s just that he’s an older player and they didn’t have to give him a two year deal last year but they did. I don’t understand why there has to be a two year cushion. A lot of great players play on one year deals when they get to the end of their careers.”
When asked about whether he could picture Ortiz ever dawning the jersey of a team other than the Red Sox, Massarotti said, “I think we’d be naive to think that a guy could only play in one place, but I think part of what works against Ortiz in this discussion is that he has demonstrated no real willingness to leave Boston. I don’t want him to leave either but oftentimes in order to get the big pay day you have to leave to get it.” However, he did say, “National League teams aren’t going to extend for him at his age, so half the market is gone right away. You factor that in and the type of salary you’re talking about, there just aren’t that many places for him to go. If he was willing to change teams five years ago there would’ve been someone out there who was willing to pay him tons of money, but he wanted to stay here.”
Jon Lester has been another Red Sox whose contract has been discussed ad nauseam this offseason. The 30 year-old left-hander is coming off of a career year, and his deal will be up at the end of the season. He did say that he’d be willing to take a hometown discount, but the deal will still be extremely lucrative.
Massarotti said, “I think he’s being sincere about taking less, but the question is less than what? If Lester thinks that he is Clayton Kershaw’s equal, then less means less than $30 million a year. If he thinks that he is Cole Hamels’s equal, then less means less than $24 million. The whole discount thing is a great term, but a discount from what? The real question is  who does he deem as a peer?” He also said, “he’s saying the right things at the moment and there’s enough reason for people to be optimistic about it, but negotiations are always complicated and you’re talking about a pitcher getting into his thirties, there will be a real risk for any team that wants to sign him.”
When asked about Brandon Workman’s potential role as a starter this year, Massarotti said, “with Dempster out of the mix, certainly there’s an opening for them, although when they go out and sign a veteran pitcher like Chris Capuano it makes you think that they really have designs of putting Workman in the bullpen. I feel like if there’s an injury he will start, but it seems like they are angling him to the bullpen.”
The left side of the infield is the final area where most of the questions lie. As of now, Xander Bogaerts is slated to begin the year at shortstop as Stephen Drew remains unsigned after rejecting a one year, $14 million qualifying offer. Will Middlebrooks is penciled in at third base for now but it is speculated that the club is not 100% committed to him at this point.
When asked if not signing Drew is an indicator for how the Sox feel about Middlebrooks, Massarotti said, “the more I think about this, the more I believe that it’s not an indicator. I feel like they feel like they have a plan B in Garin Cecchini, who was in Double A at the end of last year. If Middlebrooks can’t play, they’ll move on to the next young guy. I think that that’s how they want to operate. Cecchini by all accounts is off to a nice start at camp, not that you can tell that much at this stage.” He added, “they really do like him. If they give Middlebrooks a half-season and he doesn’t play well, Cecchini might be ready by then. I think that third base is positioned pretty well. It’s part of the reason they moved Jose Iglesias last year.”
As many unknowns as there are going into this season, the very least that can be set is that this year’s club is filled with winners. The 2013 Red Sox were a “remarkable gift of a season,” but for the 2014 team, the expectations have never been higher. Only time will tell if Boston can match them.
Felger and Massarotti airs from 2-6 p.m. weekdays on 98.5 the Sports Hub and Comcast Sports Net.