Craig Breslow will be introduced as the Red Sox new chief baseball officer on Thursday, and once those formalities are out of the way he’ll pretty much have to hit the ground running.

The World Series could wrap up as soon as Thursday night, and once it does the offseason will rapidly accelerate as free agency kicks off, the trade market re-opens and clubs face a series of important deadlines.

First up, free agency and the trade market officially open the day after the World Series ends, but free agents won’t be able to sign with new teams until five days afterwards. That means clubs will have an exclusive window to re-sign their own players.

All option decisions must be finalized within that five-day window as well, so Breslow’s first order of business will be figuring out a plan for the five Red Sox players who are either pending free agents or likely to become one.

Will they stay? Will they go? Do the Red Sox have any candidates for a qualifying offer? Here’s where things stand with each player.

Justin Turner, 1B/DH

Turner was one of Boston’s most valuable players last season, but his situation is complex and navigating it will be one of the most important challenges Breslow faces this winter.

Turner has a $13.4 million player option with a $6.7 million buyout, which means if he declines his option he’d only need to land a one-year deal worth approximately $7 million to exceed the money he’d make exercising the option. He should top that easily after batting .276 with an .800 OPS, 23 home runs and a career-high 96 RBI, so the question isn’t whether Turner will become a free agent, but how the Red Sox should proceed once he does.

On one hand, Turner established himself as a clubhouse leader and was one of Boston’s most productive offensive players, so if he leaves the Red Sox will have a big hole to fill. On the other hand, he’s about to turn 39 and at this point is best utilized as a full-time DH, which will restrict the club’s roster flexibility and make it harder to improve defensively.

There are pros and cons to either approach, but one thing that isn’t likely is the Red Sox extending Turner a qualifying offer. That would amount to a one-year, $20.5 million deal, which Turner would almost certainly accept, guaranteeing himself over $27 million for 2024 factoring his option buyout. It’s hard to imagine the Red Sox extending any of their other free agents a qualifying offer this year either.

Adam Duvall, OF

Duvall signed with the Red Sox on a one-year, $7 million deal and for the most part lived up to expectations. Though he missed two months due to a broken wrist, Duvall also hit 21 home runs and posted an .834 OPS, providing the right-handed pop the Red Sox hoped for.

Will he come back? That’ll depend in large part on what else the Red Sox do with their outfield this winter.

For much of the season the Red Sox had four outfielders seeing regular playing time, those being Duvall, Alex Verdugo, Masataka Yoshida and Jarren Duran. The simplest thing the Red Sox could do to clear that logjam is let Duvall walk and go into next season with an outfield of Yoshida, Duran and Verdugo. However, they could also trade Verdugo, move Yoshida to full-time DH or shake things up in some other way where Duvall might make sense to bring back on another one-year deal.

James Paxton, LHP

After missing all of 2022 due to injury, Paxton came back to the Red Sox on a one-year, $4 million player option and wound up becoming one of the best bargains in baseball. The veteran lefty emerged as one of Boston’s best arms following his return in May, but he ran out of gas in the second half and missed the final month of the season.

Paxton deserves a lot of credit for coming back after nearly three years away and should garner interest in free agency, but it’s difficult to imagine the Red Sox re-signing the oft-injured veteran when what they need most is reliable inning-eaters to bolster their rotation.

Joely Rodriguez, LHP

Rodriguez was the first free agent signing the Red Sox made last winter, but the talented lefty couldn’t stay on the mound. Rodriguez only appeared in 11 games for Boston and posted a 6.55 ERA, and those handful of outings came interspersed between three separate trips to the injured list.

Given that track record and his prior injury history it’s hard to imagine the Red Sox picking up his $4.25 million club option. It’s more likely they’ll pay his $500,000 buyout and let the soon-to-be 32-year-old hit the market.

Corey Kluber, RHP

This one’s a no brainer. Kluber went 3-6 with a 7.04 ERA in 15 games (nine starts) at age 37 and missed the entire second half due to injury. Expect the Red Sox to decline his $11 million club option and look to invest that money elsewhere.