Red Sox offseason schedule: Key upcoming deadlines to monitor

Red Sox Chief Baseball Officer Chaim Bloom. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
Red Sox Chief Baseball Officer Chaim Bloom. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

Upcoming deadlines for the Boston Red Sox as the offseason begins.

The World Series is over and the offseason is officially underway. It’s time to brush aside a miserable 2020 season and look forward to how the Boston Red Sox can make improvements for next year.

While we’re all eager for Chaim Bloom to get started on rebuilding the roster, the offseason is a process that unfolds in stages based on various deadlines. With the Los Angeles Dodgers wrapping up their World Series victory last night, we have now entered a five-day moratorium period before free agency begins.

During this period, the Red Sox need to decide if they are going to pick up the team option on the contract of any eligible players. This includes the $6.85 million option they hold for Martin Perez. Players with opt-out clauses must decide if they are going to exercise that option to test free agency or remain locked into their current deal. J.D. Martinez is expected to opt in to stay with the Red Sox but we’ll know for sure very soon.

Once we reach the end of this moratorium period, the excitement of the offseason begins to build. Let’s take a look at some key upcoming dates for the Red Sox.

November 1: Qualifying offers due

Players entering free agency can receive a qualifying offer from their current team. Accepting the offer means the player agrees to stay with the team on a one-year deal at a price determined by the average salary of MLB’s 125 highest-paid players. The amount this year is set at $18.9 million.

If the player declines the offer, the team receives a compensation pick in next year’s draft. The team that signs that player in free agency will forfeit their second-highest pick in the draft.

The Red Sox don’t have any likely candidates to receive a qualifying offer. There’s an outside shot they could offer one to Jackie Bradley Jr. if they believe he’ll garner enough interest on the open market to discourage him from accepting so that Boston can recoup a draft pick.

November 2: Free agency begins

Teams can begin negotiations with players who have entered free agency. Recent years have produced a cool market that can move slowly and that can be expected to continue considering the loss of revenue in the pandemic-shortened season squeezing the budgets of most teams.

Fresh off resetting the luxury tax penalties, the Red Sox should be eager to spend but players might be content to wait and see how the market develops. Don’t expect a big slash on Day 1 of free agency but the rumor mill will begin to heat up.

In addition to Bradley, Rusney Castillo and Collin McHugh are also now eligible for free agency.

November 20: Rule 5 draft protection

This is the deadline for when prospects must be added to the 40-man roster in order to protect them from being selected in the Rule 5 draft, which will be held on December 10.

Jay Groome, Bryan Mata, Connor Wong, Connor Seabold, Hudson Potts, and Jeisson Rosario are all candidates to be added to the roster. The first two are among the top pitching prospects in the organization while the others were acquired via trade within the past year.

The Red Sox will have a full 40-man roster once they account for activating players who finished the season on the 60-day injured list. They will need to clear some room in order to add these prospects, plus any other moves they make in free agency or on the trade market.

December 2: Non-tender deadline

This is the deadline to cut bait with players who are under team control but not locked into a contract. Declining to tender those players a contract allows them to become free-agents. Otherwise, they will remain under team control at a pre-arbitration salary or enter the arbitration process if they are eligible.

There are several candidates who the Red Sox could choose to non-tender. Jose Peraza is the most notable since nothing about his production this year warrants keeping him on the roster or paying his projected arbitration salary. Ryan Weber falls in the same category, although he’s projected to be cheaper in his first year of arbitration so that might give him slightly more security.

Several of the pre-arbitration eligible players might be let go in order to clear roster space for prospects and other offseason additions.

January 15: Arbitration figures due

Players who are eligible based on service time can negotiate with their team on their salary for next season. This is the deadline for when both sides must submit those figures to MLB. If the sides can’t reach an agreement, they will go before an arbitration panel that will determine which side has the fairest offer.

The Red Sox have eight arbitration-eligible players, some of whom are non-tender candidates. The most notable players in this group that we can safely say will be tendered a contract are Eduardo Rodriguez and Rafael Devers.

How much these players earn in arbitration will be a significant factor in determining the offseason budget. MLB Trade Rumors provides an annual projection of arbitration salaries that tends to be fairly accurate, giving the Red Sox a solid idea of where their payroll stands.

Five free-agents that must be avoided. dark. Next

This should be a busy offseason for the Red Sox as they look to build back up to contention. Fixing this roster can’t happen all at once though. It’s a process that needs to be taken one step at a time. Keep an eye on how the front office approaches each phase of the offseason since the decisions they make could tell us quite a bit about their plans for the next steps.