Though the season still feels very young, the Red Sox are 37 games into their schedule, and the 2014 season is closing in on the quarter-pole. There is still plenty of time left in the season, of course, and many things are going to change as the season moves on. Still, for members of the front office, looking to the future is always important, and it's never too early to start a rough plan for what to do in the coming offseason. With that in mind, let's look at the players on the roster currently set to hit free agency at season's end, and what the plan could be with them come next winter.
Easily the most notable player on this list, Lester has been hounded with questions about an extension since last season ended. Of course, to this point, nothing has gotten done, and by the reports out there, the two sides don't appear to be all that close to concluding the drama. The left-hander faced some criticism regarding his inconsistencies over the past two years (some of that from myself), but has done his best to quell those doubts with a phenomenal start this season. There's an argument that he has been the most valuable player for the Red Sox through the first month-plus of the year. With eight starts under his belt, Lester has tossed 55-2/3 innings (just short of seven innings per start), has a 2.75 ERA with a 2.12 FIP, and is striking out 30 percent of opposing batters while walking just six percent. He's done nothing but boost his monetary value as he approaches free agency, and is going to be one of the highest-paid players next winter. If he can keep up some semblance of this performance, it would be tough to see Ben Cherington let him pitch for another team in the foreseeable future.
Both members of Boston's catching tandem are set to hit the open market this winter, so I'm pairing them together. Pierzynski and Ross are both veteran players who are quickly approaching the end of their major-league careers. The former made the worst imaginable first impression here in Boston, but has started to come around with the bat. As of today, he is hitting .277/.318/.396, good for a 92 wRC+. He's no Jarrod Saltalamacchia (yes, I'm still upset about that one), but he's been fine offensively. With that being said, it's tough to imagine he will be brought back. He was brought in to be a one-year stopgap, and I can't imagine he'll be capable of doing anything to change that. As for Ross, he hasn't been great in his short time in Boston, and has just a 67 wRC+ this season. He is still a very good defensive backstop, though, and is a perfect fit for a backup role. Depending on how they feel about Christian Vazquez - and to a lesser extend, Daniel Butler - after this season, I could see him brought back to serve as a mentor as the younger catchers start to get phased into their major-league playing careers.
After the role he played in last year's World Series, it feels like Jonny Gomes has been more of a fixture on Red Sox rosters than he has been. He's in the final year of a two-year deal, and it's approaching the time to see how Boston's front office values his intangibles and clubhouse presence, along with his platoon abilities. While Gomes is nowhere near good enough to be a true everyday player, he is fully capable of being a key player with the way he can mash against lefties. And since the Red Sox's left field situation is currently cluttered with left-handed bats like Daniel Nava, Mike Carp, Grady Sizemore, that is a valuable thing. Still, there's a reason that Gomes has played five different teams in his career. It's a role that can be relatively easily filled. For Boston, that hope comes in the form of Bryce Brentz. Like Gomes, Brentz doesn't figure to be a true everyday player during his career. However, he is a right-handed power bat, plus he's much more reliable defensive player. He's paid his dues at AAA, and the Red Sox can use the money they'd spend of Gomes to shore up other areas, probably in the form of paying Lester a bunch of money.
I think this is probably the hardest one of these to write, because no one knows who the hell Grady Sizemore is at this point. He stole our hearts in spring training, then tore them up with a really bad stretch in April, and now he's hitting again and we're just getting sick of him leading us on like this. With a player like Sizemore, the allure of his potential will never be easy to give up, but the fact is that he's hitting just .227/.296/.361 (79 wRC+), right now. His .263 batting average on balls in play could be chalked up to bad luck, but maybe he's just a low BABIP hitter now. The point is, we really have no idea what kind of player he is, and its tough to make future plans on that kind of player.
Peavy, of course, came over in last year's biggest trade for the Red Sox, when they dealt Jose Iglesias to get the right-hander. The move worked out, as it gave the team some needed pitching depth, and helped win them a World Series. This year, the results have been pretty good, but they certainly don't seem sustainable. A quick look at his 3.09 ERA would lead to positive thoughts, but a deeper look, specifically at that 13.5 percent walk-rate, is a bit of a downer. In fact, Peavy has walked at least four batters in five of his seven starts in 2014. Given his track record, I'd expect that walk-rate to drop soon, but there are other worries. Most notably are the home runs. As a fly ball pitcher, he was able to thrive in his early days in San Diego, but in the AL East and its smaller ballparks, that is a tougher task. He's an important part of the 2014 team, and should keep his rotation spot all season, but on Opening Day 2015 I'd expect to see him in a different uniform. The Red Sox just have too many up-and-coming starting pitchers, and Peavy is the easiest spot in the rotation to open up right now.
For most of last season, we assumed that Uehara was set to hit the open market after last season, as it appearaed that his contract was just a one-year deal. However, in a surprising turn of events, it turned out that he had a vesting option that added this 2014 season onto his deal, and the Red Sox got another bargain season from one of the more dominant relief pitchers in the league. He hasn't been quite as amazing this season, but his 1.15 ERA and 24/3 K/BB ratio is still pretty incredible, especially considering he says he hasn't felt like his mechanics are right. Health is always a concern for a pitcher of his age, but as long as he can pitch, the Red Sox should keep him. He's quickly become a fan favorite, and the team is much better with that kind of reliable arm pitching at the ends of games. I'd expect him back in 2015.
Miller is probably my favorite player on the Red Sox right now, so I'm going to get this out of the way and say I'm a little biased. I want him extended today. Of course, that's probably not the road to take with a middle reliever who has had control problems throughout his career. Despite the control issues, the big lefty has made huge strides since converting full-time as a reliever, and has used that success to catapult him into a setup role in the current bullpen. His success is carried by his incredible strikeout rate (35 percent last year, 36 percent this year) that makes him a dominant force in pressure situations. When the team needs a big strikeout late in a game, there is no better man to call on than Miller. At the moment, he has walked just 6.4 percent of the batters he's faced, and if he keeps that up, the case to keep him around becomes pretty straight forward. At his best, he is an incredibly useful asset, and a perfect complement for Junichi Tazawa in the seventh and eighth innings. While Boston has many arms coming up, none of them are lefties with the type of stuff that Miller has. He has a very good chance of convincing the Red Sox to keep him around beyond this season.
There is still plenty of time remaining on the Red Sox's schedule, and opinions about these players will likely change as we approach the later months. However, the cases for a lot of them are pretty straight forward. To me, the only players' whose cases are up in the air are Sizemore and Miller, and possibly Uehara depending solely on his health. The roster is always a fluid situation, but you can bet that Ben Cherington is paying extra close attention to these players this season.