by Jacob Gurvis

Now that the calendar has flipped to November, it’s back to work for the Red Sox. While it has only been a little while since they won the World Series, there is work to be done. As shown in the disappointing years after Boston’s last two championships, 2005 and 2008, it is important not to forget about “the next season.”

With 2014 just around the corner, four major free agents, Stephen Drew, Jacoby Ellsbury, Mike Napoli, and Jarrod Saltalamacchia, are all looking for new deals. The Sox have tough decisions to make, as they could be looking for new players to fill centerfield, first base, and catcher.

Shortstop is less of a necessity, with the impressive Xander Bogaerts waiting for his turn. However, Bogaerts played only third base for the Sox last year, and they want Drew back.

The Red Sox have extended qualifying offers of 1 year/14.1 million to Drew, Ellsbury, and Napoli. All three players have declined the offers, as they all look for more money. Napoli is reportedly looking to explore free agency, despite having a multi-year offer from Boston.

The odd player out was Saltalamacchia, who didn’t receive the offer. But that does not mean he will not re-sign. Farrell has said multiple times he wants “Salty” back.

General Manager Ben Cherington said that ideally, all four guys would be back next season (and beyond.) In an interview, he said, “Really with all of our free agents, there’s interest in every one of them. I also think it’s unlikely that every one of them will be back, just because that’s the nature of the game. It’s difficult to do that.”

So what to do with them? Very difficult question. In my opinion, I think that all of them should be brought back for the future. In reality, there is no chance all four guys re-sign. It’s even likely that none of them will. And even if they all wanted to come back, they couldn’t afford that. But in a an ideal world, the 2014 Red Sox would be nearly identical to 2013. So let’s look at those four guys one by one.

First, the best and most difficult player, Jacoby Ellsbury. Ellsbury is extremely talented. When he’s healthy, he can be an MVP player. While he has been hurt a lot so far in his career, his 2011 stats prove his skill. He hit 32 homers with 105 Runs Batted In (RBIs) and 39 steals. In 2013, he stole 52 bags. So he’s very good. He also has Scott Boras as his agent, which naturally means he will get overpaid. However, despite many fans’ concerns with giving him a long term deal, I would do it. I would give him somewhere in the 6 year/ 110 million range. Ellsbury is 30, so I think anything more than 6 or 7 is a mistake. He deserves a payday, and he supposedly wants to stay in Boston.

Next, slugger Mike Napoli. Despite contract issues prior to 2013 caused by complications with his physical, Napoli was great. Sure, he struck out a lot (187 times), but he also hit 23 homers and had 92 RBIs. Napoli played an elite first base, and was one of the better fielders at that position in all of baseball in 2013. Napoli is 32, so a relatively short-term deal is really the only option. I would give “Nap” the 3 year/39 million deal he almost got prior to 2013. Sure, he’s a year older. But he proved that he is worth it, and he fit in well with the Sox.

Now Stephen Drew, who presents a difficult decision. With Drew’s success in 2013, it makes sense to bring him back. Drew had a great year, and despite being unfairly hated by many fans, he was very productive both offensively and defensively. Drew hit 13 homers with 67 RBIs, and was stellar on defense. He may strike out a lot (124 times in 2013), but he’s still a solid player. Drew struggled in the playoffs, seemingly striking out every at-bat, but he proved to be a crucial piece to the bottom of the Sox’s order, and secured the shortstop position all season. Drew is 30, and I’d give him around 2 years, 30 million.

Finally, we have Jarrod Saltalamacchia. Salty had another great offensive season in Boston, with 14 homers, 65 RBIs, and 40 doubles. Salty improved his defense from prior seasons, and was a consistent and trusted backstop. He is only 28, and does seem to be getting better. Salty did not receive a qualifying offer, but both Cherington and Farrell have expressed interest in re-signing him. Another free agent catcher, Brian McCann is also drawing interest from the Red Sox. It’s difficult to decide who to sign here. They are very similar players. McCann, 29, is better defensively and slightly better offensively. But Salty may come at a cheaper price, and is already known and loved in Boston. He wants to come back. I would go with Salty here. It’s close. But I’d give him 6 years and around 70 million.

This offseason is important. “The year after” is always a test of a team’s true depth and youth. The Sox have important decisions to make, with four good players hitting the open market. It would be great if they all came back, but that is very unlikely. There’s always Brian McCann, Xander Bogaerts, Will Middlebrooks, Carlos Beltran (who the Sox are making an “aggressive push” for) and many other options for Boston. There are limitless different combinations for how the 2014 Sox could shape up, with returning players, free agents, and trade candidates. There’s no way to predict what will happen this winter. Let’s just hope we see at least a few of these loved champions back in Boston in 2014 and beyond.