Copyright The Boston Herald

As the World Series winds down the baseball offseason is about to kick into high gear, and in the coming days we’ll start having clarity on important offseason business like who will opt out, whose options will be picked up or declined, who will hit free agency, and a whole lot more. What can fans expect as the offseason begins, and what should be the Red Sox’s top priorities? The Herald’s Red Sox reporters, Mac Cerullo and Gabrielle Starr, discuss. Should Sox bring back Giolito? Mac Cerullo: Well Gabrielle, October is nearly over and the hot stove is about to heat up. We should start seeing a flurry of activity over the next week or so, but there’s one order of business I think we should start with, and that is Lucas Giolito. Giolito was one of Boston’s most important players last season and the Red Sox wouldn’t have made the playoffs without him, but he also got hurt again right before the postseason and has a mutual option that will almost certainly be declined. So assuming Giolito hits free agency, should the Red Sox try to bring him back? Gabrielle Starr: If the mutual option is declined, which, as you said, is likely, Giolito will certainly be among the most intriguing starting pitchers on the free agent market. He was largely excellent this year, but he was struggling down the stretch for a few weeks before any injury announcement, and he missed all of last season due to elbow surgery, as well. It will be interesting to see how prospective teams balance the bulk of his career as a largely healthy player with the inevitable recency bias from his two injury-impacted seasons in Boston. I know the Red Sox like Giolito a lot, both as a pitcher and a clubhouse man, but something tells me the risks involved with signing him will limit how far they will be willing to go to re-sign him. What do you think? MC: I think a best-case scenario would be something like what happened with Nick Pivetta last offseason. The Red Sox extend him a qualifying offer, he declines and then winds up signing with another team. That way the Red Sox get an extra draft pick and have both a rotation spot and Giolito’s salary freed up to pursue another option. Giolito had a great season, but if the goal is to add a No. 2 starter and improve the starting rotation, the idea should be to bring in someone better than Brayan Bello and Giolito. The Red Sox have enough rotation depth that there wouldn’t be much of a point in adding a No. 2 and keeping Giolito, so if he declines the qualifying offer I feel like the Red Sox would be content to let him walk. GS: Agreed, though in terms of leadership and his baseball mind, I think he brings more value to a team than people realize. Especially a team with so many young pitchers. What if Trevor Story opts out? GS: It feels like Alex Bregman’s impending opt-out is totally overshadowing the fact that Trevor Story can opt out this offseason, too. MC: That’s an interesting one, and it’s a little more complicated than Bregman since the Red Sox could void Story’s opt-out by adding an extra year to the end of his contract. Would they do that? Would Story still opt out knowing that third year might be the best he could get rather than a real crack at free agency? I think regardless of the specifics, Story will be back next year. He was arguably the team’s best all-around position player last season and given Marcelo Mayer’s health concerns and the club’s overall lack of power, the Red Sox really can’t afford to be without Story. GS: I think Story feels a strong sense of loyalty to the Red Sox for standing by him through all of the injuries and on-field struggles, which is why he always seemed less likely to opt out than Bregman. That said, it’s hard to imagine Story being better positioned to test free agency than he is right now, after his highest game total since 2018, and leading the team in a multitude of offensive metrics. I also think there will be many players looking for the security of longer-term deals this offseason before the Collective Bargaining Agreement expires next year and brings unforeseen changes to the game’s financial structures. The last round of CBA negotiations and the 99-day lockout were pretty disastrous, and it’s hard to envision smoother sailing next offseason. MC: Story knows that better than anyone. He didn’t sign his deal with the Red Sox until late March thanks to the lockout. Can you believe he basically had no spring training and welcomed a child during that first week in Boston? What a whirlwind. That is a good point about now being the best time to strike. I guess the question Story has to ask himself is can he beat three years and $75 million on the open market? If he opts out, the Red Sox don’t pick up his option and he can’t get more in free agency, then he’d probably be better off riding things out. But given his production this past season and the relative dearth of middle infield options on the market, my guess is he could get at least that much from another team, which would make opting out kind of a no-brainer. Red Sox trade candidates? GS: The Red Sox kept most of their quote-unquote core intact last offseason, but I don’t see that being the case this year. The core changed a lot during the season, with the Rafael Devers trade, Roman Anthony making his long-awaited debut and signing his extension, and all the injuries. If Craig Breslow takes a page out of Dave Dombrowski’s 2016-18 offseason playbook, he will look to build on this year’s success by adding proven major league talent, in particular, a big bat and a No. 2 starter. Integral to that process will be clearing some of the roster logjams, especially in the outfield. I’ve been told the Red Sox will look to trade either Jarren Duran or Wilyer Abreu. I also think they have to at least attempt to trade Masataka Yoshida, whom they don’t seem to want playing the outfield, which essentially makes him Devers 2.0 in the designated hitter role. Who could you see them trading? MC: Some combination of those three are kind of no-brainers, but I think a much more interesting possibility is who the Red Sox could trade from their pitching staff. Think about it. Suppose the rotation next year includes Garrett Crochet, Brayan Bello and either Lucas Giolito or an external addition. That means the rest of the rotation would include two of Kutter Crawford, Patrick Sandoval, Hunter Dobbins, Richard Fitts, Kyle Harrison, Connelly Early or Payton Tolle. They may not even have enough room to accommodate all of those guys in the WooSox rotation! So I could absolutely see the Red Sox trading from that group, particularly one of Fitts, Dobbins or Harrison, all of whom have shown promise but who might not have a clear lane in Boston. GS: See, this is also why I keep telling everyone that the Red Sox need a big bat far more than they need more pitching! Obviously, they will look to improve pitching quality this offseason, but the quantity is very clearly there, and I, too, could see them moving at least one of the arms you mentioned. A big-league ready-ish pitcher with several years of club control would definitely pair nicely with Yoshida in a trade package. MC: Plus, let’s not forget about all of the pitching prospects the Red Sox have drafted recently. The system is bursting at the seams with talented young arms, so if acquiring a big bat or a No. 2 starter meant parting with a top recent pick like Brandon Clarke or Marcus Phillips, the Red Sox are better equipped to give up a talent like that than they’ve probably ever been. Under the radar targets? MC: So obviously everyone knows about the big names who would be obvious fits in Boston, people like Pete Alonso, Kyle Schwarber or Joe Ryan. But the Red Sox have less obvious needs as well, and last year the club’s first acquisition wasn’t Crochet or Bregman, but veteran lefty Justin Wilson. Care to take a crack at who the Red Sox might target first this year? GS: Funny enough, I think one priority is someone close to home: Rob Refsnyder. If the Red Sox plan to trade from their outfield core, they will need the depth he provides, and his ability to absolutely torment left-handed pitching is incredibly important. I don’t think people realize how different this season would have gone without him in the lineup against southpaws. Refsnyder is also one of the most respected veteran voices on a very young team that could be losing as many as three vets in Bregman, Story, and Giolito. MC: I could see that. In terms of external additions, the Red Sox have a couple of lefty relievers due to hit the open market. If Wilson or Matz don’t return, I wouldn’t hate it if the Red Sox went out and got Gregory Soto. He’s a two-time All-Star with closer experience, and while his past couple of seasons haven’t been stellar, he still has great Statcast metrics and with some fine-tuning could re-emerge as a high-leverage bullpen piece. GS: Agreed. Lefty relievers were a priority last offseason, and their success would certainly suggest a repeat is due. Since you mentioned Alonso, how do you think the Red Sox tackle the first-base situation this winter? Obviously they have Triston Casas under club control, but after his injuries the last two seasons, Breslow is rightfully taking a noncommittal tone. MC: I think it depends heavily on whether they land Alonso or not. If they get him, that’s your answer and Casas likely becomes the preferred option at DH, with Yoshida likely starting the season there if he’s still with the team and if Casas is still recovering from his injury. Short of that or another high-profile option like Josh Naylor, I could see the Red Sox riding it out at first with a combination of Casas, Romy Gonzalez and Kristian Campbell. As long as the club gets a power bat elsewhere then it still makes sense to give Casas a chance. He’s proven he can produce at a high level when healthy, and if everything clicks he could be a big part of the solution to Boston’s power problem. GS: You’re probably right, but I wouldn’t put it past Breslow to pull off something stunning, either. And after the World Series ends this weekend, the Red Sox can finally get started.