1. Jason Bay: As everyone not in a coma knows, the Red Sox leftfielder is a free agent this offseason. He and his agents were unable to come to an agreement with the Sox during the season, but Bay seems like a reasonable guy who has enjoyed playing for a contender. Theo's not going to overpay, but I'd say something like four years, $60 million should get things done.
2. The revolving door at the shortstop position: It's no secret that shortstop has been a bit of a problem since about... ohhh... 2005? Now, most of the fans I've talked too support picking up Alex Gonzalez's $6 million option for next season, but Theo recently made comments on WEEI that insinuated he is less than impressed. Gonzo has hit very well with us, but above his usual production. I've heard rumors about Stephen Drew (JD's younger brother, currently with the Diamondbacks), who is just Theos type. Throughout his career, his strikeout numbers have consistently declined, while the walks have steadily increased. I would be okay with another Drew on the team.
3. What's going to happen behind the plate: It's no secret that Captain Varitek had a BRUTAL second half. We can only assume the team will decline to pick up his $5 million option, but Jason has a player option he can activate for $3 million. I for one hope Varitek sees the light, swallows his pride, and calls it a career: the Sox would do well to hire him as a coach, though he's said in the past that coaching doesn't interest him. Victor Martinez had an electric bat for the Red Sox down the stretch, but he's essentially a younger Varitek: good game calling skills, good repertoire with the pitching staff, quality bat for a backstop, but not so good at throwing out basestealers. VMart has a club option, and I'm guessing that Theo will pick it up, while poking around for other possibilities... Joe Mauer would be the definition of a long shot, but a girl can dream, right?
4. The aging meat of the lineup: David Ortiz will be thirty-four next season (if you're cynical, like me, you might speculate he's a bit older, like many Dominican players), while Mikey Lowell turns thirty-six in February. Mike's bat looked fine this season, but his range was severely diminished due to the labrum surgery he had last offseason; the rest he had down the stretch seemed to help, but he didn't like sitting. Papi managed to finish with almost respectable numbers, but looked positively anemic in the short ALDS. We need both of them at their best, or the lineup won't be nearly deep enough.
5. Who's manning the bench: Baldelli was signed to a one-year deal last year, and he's been less than dependable. Kotchman plays a steady first base, but if Lowell can't go every day we'll need someone really good to hold down first base while Youk slides to third. I trust Theo will find a gem somewhere.
6. The back of the rotation: Tim Wakefield is forty-three years old, with a balky back, and minor shoulder problems. While the shoulder issue is old news (Wake plans to have it surgically repaired after he retires), the back is more problematic. However, Tim isn't the type to come back if he doesn't feel he can contribute, but if he can get the back fixed, I'd say he's as good an option (for the first half, anyway) as anyone, and at $4 million, it's reasonable.
7. What's going on with the bullpen: Obviously, Paps picked a TERRIBLE time to have a meltdown, but he's still a premier closer. In the same game that Cinco Ocho besmirched his postseason ERA, Daniel Bard proved he could be cool under pressure: coming into a bases loaded situation with no outs in an elimination game, and giving up just one run (on a double play ball). If the Sox development machine thinks Bard is ready to be a closer, I wouldn't be shocked if Theo traded the bigmouthed Papelbon for a big bat (Prince Fielder is rumored to be available).
8. Daisuke's offseason regimen: Matsuzaka came into camp in terrible shape, and then there was that public disagreement with the Red Sox strengthening program. However, he seemed genuinely contrite when he got back from the Disabled List in September. I'd like to think he'll be more responsible this winter... otherwise, I say the Japanese WBC team can pay his salary.
9. Tito's health: This one went under the radar this season, but the manager is far from perfectly healthy. I have nothing but the highest esteem for the Red Sox manager, and I know he'll use the offseason to get himself rested and ready for next year... But how long is he going to hold out? Is John Farrell staying on in his job as pitching coach because he knows that Tito is planning to step down in the next few years? This is wild speculation, but you have to admit, it makes sense...