A few pressing questions for the Red Sox….

The duck boats have yet to be parked following Saturday’s celebratory parade, but some pressing business is already upon Red Sox general manager Ben Cherington and his baseball operations staff.

John and Ben share the trophy

In the wake of their third World Series triumph in 10 years, Red Sox players have expressed deep admiration for one another. As much as any team in recent memory, this was a united crew. To a man, they would love to keep it together.

Yet to a man, they understand that business often comes first, and Boston will have a different look when it reconvenes in Fort Myers to begin the process of defending its crown. Red Sox president Larry Lucchino admitted as much Friday morning.

John Tom and Larry Celebrate
“I can’t give you a precise answer as to how many players will come and how many will go,” Lucchino said in an interview on Boston sports radio station WEEI. “We love the core of this team. We know the core of this team will be here and be with us. We know we have some new players who were signed for a couple of years, like Jonny Gomes and David Ross. So we do know that the core of this team will remain. But there’s absolutely no chance that the 25 guys who finished in the World Series will be the same 25 guys who will start Opening Day next year.”

Seven Red Sox players were among the 147 players who officially filed for free agency Thursday: catcher Jarrod Saltalamacchia, first baseman Mike Napoli, outfielder Jacoby Ellsbury, shortstop Stephen Drew, relief pitcher Joel Hanrahan, infielder John McDonald, and pitcher Alfredo Aceves, who was exiled to the minors last season.

Free agents can begin to sign with new teams beginning at 12:01 a.m. ET Tuesday. Until that time, they are not eligible to negotiate contract terms with a new team, although they and their representatives are allowed to talk with any team about a potential match. Teams retain exclusive negotiating rights with their free agents until that time.

But in the interim, the Sox must also decide whether they will extend a qualifying offer to their free agents, which determines whether they will receive draft-pick compensation if a free agent leaves.

Qualifying offers must be extended by 5 p.m. Monday. The value of a qualifying offer has been calculated by formula to be a one-year guarantee of $14.1 million for 2014. Any player accepting a qualifying offer is considered to be a signed player. A free agent has until 5 p.m. on Nov. 11 to accept a qualifying offer. If he declines a qualifying offer and signs with another big league team, his former team receives an amateur draft choice as compensation, while the signing team forfeits its highest available draft pick and the accompanying bonus pool money in the draft.

Stephen DrewWhat do you do with the left side of the infield?  Shortstop Stephen Drew is a free agent and will be coveted in a market that features very little at the position. Because of that fact, he may be inclined to turn down any qualifying offer (one year, $14.1 million) the Red Sox give him and seek a long-term deal elsewhere. If that’s the case, Xander Bogaerts slides right on in, likely leaving Will Middlebrooks to man third base.

But is that ideal for the Sox?

Middlebrooks’ up-and-down (but mostly down) 2013 campaign, coupled with a lackluster October, casts some doubt as to whether he is ready to be an everyday player in the majors. Meanwhile, Bogaerts looked like a 10-year veteran as the club’s third baseman in the World Series. Both he and the organization have said Bogaerts is a shortstop, but another year (at age 21) at the hot corner would not hinder his future at another position.

Xander WS 2013

At the same age, Cal Ripken Jr. played the first half of his first full season at third base. Perhaps if the team finds a way to keep Drew, who doesn’t turn 31 until March, Bogaerts could do the same and Middlebrooks could be dealt or moved across the diamond to first base, if Mike Napoli moves on.

Will Salty return?  Jarrod Saltalamacchia told ESPN prior to Game 6 that he had already wondered if he was spending his final few days as a Red Sox. David Ross, who is signed for next year, was John Farrell’s choice in the final three games of the World Series.

It seems as if we have been hearing his name forever, but Saltalamacchia is still just 28 and is coming off his best all-around offensive season (.273 average, 14 homers, .804 OPS). He fits in the clubhouse and with the pitching staff, and if the Sox see him continuing to improve defensively, a qualifying offer could be in the cards.

That could change if the organization feels that Ryan Lavarnway is ready enough to split time with Ross, or if it makes a push for someone like free agent Brian McCann. Prospect Blake Swihart could be knocking on the door in another year or so, and Christian Vazquez had a solid season at the plate and behind it at Double-A Portland, so more help is on the horizon.

Lester Game 5What’s the long-term future of Jon Lester?  Boston will exercise its option for Lester for next year, which carries with it a $13 million price tag. His value is at an all-time high after a brilliant October (4-1 with a 1.56 ERA in five starts), and discussions of a long-term deal may be forthcoming.  The Sox gave Josh Beckett and Clay Buchholz lengthy, pricy extensions in recent years. They also gave John Lackey a five-year, $82.5 million deal and Ryan Dempster a two-year, $26.5 million contract, then took on Jake Peavy’s $14.5 million salary for 2014. If there’s anything left over, locking up a durable, homegrown ace who is not yet 30 seems like a no-brainer.

What about David Ortiz?  While similar to Lester in some ways, the Ortiz situation is a little murkier. Many observers felt as if the organization had lost its mind when it gave the slugger, at the time 36 and rehabbing from an Achilles injury, a two-year deal that will now total $30 million due to an achieved incentive this year. When that contract expires after the 2014 season, would Ortiz — who would then be approaching 39 — seek one more multiyear deal elsewhere? And do the Sox want to prevent one of the cornerstones of their franchise from leaving?

As crazy as it seemed to lock him up last offseason, it would be awkward to let the World Series MVP go too far into the final year of his deal with an uncertain future. An extension beyond 2014 could be in his future.

Ells Fenway WSBid adieu to Jacoby Ellsbury?  There have been whispers for months that the two sides are far apart in negotiations. ESPN’s Buster Olney reported this week that a $30 million gap existed after Ellsbury’s phenomenal 2011 season and that the sides could not get together again after his down 2012. With Ellsbury a Scott Boras guy, the long-held assumption has been that the center fielder has been waiting to test the free-agent waters. Coming off a much better 2013 (.298 average, 52 steals) seems like a great time to do so.

Boston’s aggressiveness in this matter rests largely in its opinion of Jackie Bradley Jr. The youngster had a rough time in his first stint in the big leagues in April but looked a bit more comfortable in his Red Sox skin once he was called up again in September, even getting support from some to be included on the postseason roster.

Bradley will not disappoint in the field; he has range and a great arm. Enduring some growing pains at the plate would hurt much less than paying Ellsbury upward of $18 million when he is 36 and beginning to break down. Not saying that would necessarily happen, but it’s the risk you run with big-money long-term deals, and Bradley will come at a pittance as he approaches his prime.

Who’s on the bench?  The 2013 Red Sox did not have many holes. However, there were times when it felt as if they needed one more utility guy in the infield. Brock Holt and Brandon Snyder did not impress in their brief stints, and once Jose Iglesias left, there was a relative lack of options some nights if one of the starters went down.

To illustrate the conundrum, Middlebrooks stood as Dustin Pedroia’s backup for a handful of games. Veteran John McDonald was brought in late to add an extra hand, and Bogaerts’ call-up gave the club another option, but the organization would do well to bring in an Alex Cora-type who can ably back up multiple spots. Someone with speed who can play center would help even more if Ellsbury leaves and Bradley needs a backup.

Buch delivers WSLester-Buchholz-Lackey-Peavy-?  Pencil in Lester, Buchholz, Lackey and Peavy as the top four starters. Who gets the No. 5 spot? Felix Doubront made strides in 2013 and figures to have earned it, but Dempster is on the books for $13.25 million. Also, waiting in the wings are a few young, intriguing arms who could make a push, including Allen Webster and Anthony Ranaudo.

Chances are Doubront gets a spot, Dempster serves as an expensive long man/spot starter, a la Tim Wakefield late in his career, or gets traded, and the youngsters are given more time to prepare for when somebody goes down.

And somebody will go down.

Felix in the 2013 WS
The Sox were actually quite fortunate to suffer only one long-term injury among starters, that being Buchholz’s three-month absence. There will be injuries, and having the depth to atone for them is as important as anything through the course of a long season.

Nap rounds the bagsBring back Nap?  “I want to be here. I love this place.”

That was Mike Napoli after the World Series triumph. Lines like that one are thrown around like empty beer cans during such celebrations, but it is clear that Napoli has been a nice fit in Boston.

Napoli’s agent told the Boston Globe that his client would not accept another one-year deal, and that the club would analyze the condition of Napoli’s hips to see if there has been any significant wear and tear since the last checkup. With a clean bill of health, perhaps something like the three-year, $39-million deal that the two sides reportedly agreed on last offseason — before the discovery of the hip condition altered things — could become a reality. Napoli agreed to a $5 million base salary for 2013 but earned the full $13 million with incentives.

Napoli 2013 WS

The Sox will likely make a qualifying offer to Napoli and receive a draft pick if he elects to move on, but expect the man who ranked second on the team in home runs (23) and RBIs (92), and who surprised some with a quality showing at first base, to return.

The easy decisions on making qualifying offers include Ellsbury, who is expected to be one of the most highly sought free agents on the market, and Napoli, one of the few power bats available on the market. Neither is likely to accept a qualifying offer, given the certainty of receiving multi-year offers from multiple teams.

McDonald and Aceves, whose value falls far below the $14.1 million qualifying mark, will not receive qualifying offers. The Sox also will not tender a qualifying offer to Hanrahan, who said in October he had just begun throwing 60 feet and will not be ready for the start of the season after undergoing reconstructive elbow surgery in May.

That leaves two players, shortstop Drew and catcher Saltalamacchia. First, Saltalamacchia: At 28, he is the youngest catcher on the free-agent list, and unless the Sox decide to go all-in on free agent Brian McCann, a qualifying offer makes sense, which would buy some time while prospects like Blake Swihart and Christian Vazquez develop, yet spare them from a long-term commitment. It also would assure them of draft-pick compensation if Salty leaves. Drew is also one of the better options in a light shortstop market, and while the Sox have his replacement in the wings in Xander Bogaerts, there would seem to be little downside to extending a qualifying offer.

Will the coaching staff remain intact?  Those who toiled under Farrell received loads of credit this year, particularly Juan Nieves for his work in turning around the pitching staff, Brian Butterfield for his defensive genius and Torey Lovullo for his overall work in helping to create the most complete team in all of baseball.

Lovullo is being linked to the Chicago Cubs’ managerial vacancy. Cubs president Theo Epstein is obviously familiar with Lovullo, who has interviewed for jobs in the past. Farrell said earlier in the World Series that he expects Lovullo, and others, to get their shots.

Farrell and Butterfield worked together in Toronto, and Butterfield was brought over after Farrell got the managerial job in Boston. He has also interviewed for vacancies, but perhaps these two will establish something like the Terry Francona-Brad Mills partnership that survived many years in Boston and was rekindled this season in Cleveland.

On Nov. 11, the general managers’ meetings begin in Orlando, where talks about potential trades often percolate, with the winter meetings following a month later, also in Orlando.

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