Mailbag: 'What if' questions and more

Editor's note: This is part of an occasional mailbag series on the Red Sox.Click here to ask Curt a question for his next mailbag.

Q. Hey Curt, i know the Sox had a lot of injuries, but even if they were healthy, do you think they would have been a playoff team? I'm not convinced. The Rays are on pace to win 98 games and the Yankees 101. -- Harry (Boston)

A. I don't think they make the playoffs healthy. Their pitching just didn't get consistent this year and I don't think they make those games up. The issue is that same staff could be the game's best next year, or it could be another year of mediocrity. I tend to fall into the camp that it'll be markedly improved next year and, if healthy and a few holes are plugged, should be right on pace to win 95-100.

Q. What do you think the Red Sox's biggest need/issue is this offseason? If you were Theo, what is the first thing you would do? -- Barry V. (Hingham)

A. Shore up the bullpen and decide where Youk should spend the rest of his career. Either trade or sign a long-term fixture for the corner opposite Youk. Figure out how Jacoby is going into next year and where the young outfielders fit into the mix. Sign Tito to an extension.

Q. Hi Curt, how hard is it to play out the season when it looks pretty clear that you're not going to make the playoffs? -- Jerry (Boston)

A. It's never, and I mean NEVER hard if you love the game. Every day you're out there is a chance to do something no one's ever seen before. If you are out of it then you look at the schedule and try and figure out who else you can screw out of an October berth and look at those series as your postseason.

Q. Hey Curt, who do you think will be Boston's opening-day starter at shortstop next year? -- Larry J. (Cape Cod)

A. Scutaro

Q. Hey Curt, what's your take on what the Sox should do with Ortiz this offseason? I want him back, but how many years and how much money can you really give him? -- Billy T. (Hanover, N.H.)

No idea. I would be surprised if the option is not picked up simply because there are some other things to fix/mend/look at. It's basically a one-year deal and you can assess as you go. In this day and age, one-year deals are gold to teams that spend money because they are never more than a season from having that money freed up.

Q. Curt, do you expect Jason Varitek to be back with the Red Sox next season? -- KT (Texas)

A. That has everything to do with what they do with Victor. I think he's come a long way this year, but I don't know what they feel internally. If he is the option they go with, then that means they need someone to catch 40-50 games next year since it's clear (to me, anyway) his offense is directly tied to him NOT catching 145 games a season, and instead being DH and playing first base one to two times a week.

Q. Hi Curt, do you think Tim Wakefield is pitching his final season with the Red Sox? -- JT (California)

A. No idea. Either way, it's been a phenomenal run. He's been a guy who's worn every hat and performed admirably doing it. He's also getting to an age where you aren't doing him nor the team any favors by not having a fixed role for him to pitch every X days. I still think there is merit to going to a 5.5- to 6-man rotation over the course of a season if you have the arms. The Sox are one of the few organizations that actually had the arms to do it.

Curt Schilling, who pitched for the Red Sox from 2004-08, is a three-time World Series champion, six-time MLB All-Star and founded 38 Studios. Curt and his wife, Shonda, have raised money to fight ALS (Lou Gehrig's disease) through Curt's Pitch for ALS, and have encouraged awareness for sun protection through the SHADE Foundation. They recently announced their support for the Asperger's Association of New England after their third child was diagnosed with Asperger's Syndrome.