Red Sox chief baseball officer Chaim Bloom is in full planning mode with the goal of putting together a much-improved roster compared to the one that finished in last place in the American League East in 2020. There are many key dates and decisions over the coming weeks. Here is a primer.

Which players are free agents?
Center fielder Jackie Bradley Jr. and right-handed pitcher Collin McHugh.

Did either of them receive qualifying offers?
There was an argument to be made for the Red Sox extending a qualifying offer to Bradley to make sure they get Draft compensation should he sign elsewhere, but they did not do so before the deadline.

Which players had options and when did those need to be decided?
The Red Sox held a $6.25 million option on lefty Martín Pérez, which they declined to pick up. Pérez is someone who can take the ball every fifth day, so letting Pérez go adds more weight to Boston's offseason pitching search.

Did anyone have an opt-out clause?
For the second consecutive year, slugger J.D. Martinez had an opt-out clause. He didn’t exercise it last year after an All-Star season and it's no shock MLB Network insider Jon Heyman reported Martinez made the same choice in 2020 -- which was one of the worst seasons of his career. Martinez will now stay in Boston and restore his value. If he has a big year, he could potentially opt out again after 2021.

Who needs to be added to the 40-man roster this offseason to avoid the Rule 5 Draft, and do they have a crunch for roster spots?
The Red Sox have several of their Top 30 Prospects, as ranked by MLB Pipeline, who need to be moved to the 40-man roster this offseason. The list is led by righty Bryan Mata (No. 4), lefty Jay Groome (No. 7), outfielder Jeisson Rosario (No. 16), catcher Connor Wong (No. 19), infielder Hudson Potts (No. 20) and righty Connor Seabold (No. 23). The last four players were all acquired in trades by Bloom within the last year.

Given the subpar performances in 2020 by many of the pitchers on the 40-man roster, it shouldn’t be too tough for Bloom to carve out space. One interesting thing to watch is if Dustin Pedroia again takes up a 40-man roster spot for the entire offseason, even though it seems highly unlikely he will play again. Pedroia has one year left on his contract. Teams must reset their 40-man roster by Nov. 20.

• 5 biggest questions facing Red Sox this offseason

What kind of help do they need? Will they be active in free agency? Who might they target?
In case you hadn’t heard, the Red Sox need pitching of all kinds. The entire feel of the team would change if it had more stability with the starting rotation. The outspoken Trevor Bauer, who also happens to be an excellent pitcher, is an enticing free-agent candidate if Boston is willing to spend. How about a reunion with Jon Lester? The Cubs and Lester hold a mutual option of $25 million for 2021 that includes a $10 million buyout. Charlie Morton, the righty Bloom is plenty familiar with from the one season they overlapped with the Rays, could also help.