A fourth last-place finish in the last nine seasons leaves the Red Sox with a busy offseason of trying to get this proud franchise back to a period of sustained success.

With that in mind, many questions face chief baseball officer Chaim Bloom as he begins his first full offseason with the club.

1) Who will manage?

Now that the World Series is over, Bloom can decide if bringing back Alex Cora to manage is the right thing to do. Cora’s suspension for his role in the Astros’ sign-stealing investigation during the 2017 season -- at which point he was bench coach -- expired once the World Series ended.

Up to this point, Bloom has been evasive when asked about bringing Cora back. If Cora did come back, it would be a popular move in the clubhouse, where he earned many backers during his two seasons as manager. It would also provide some fan excitement at a time the Sox are coming off a last-place season.

Bloom has already interviewed Cubs third-base coach Will Venable, Pirates bench coach Don Kelly, D-backs bench coach Luis Urueta and Marlins bench coach/offensive coordinator James Rowson, among others. Phillies director of integrative baseball performance Sam Fuld and Athletics quality control coach Mark Kotsay are two others who could get a look. 

2) Who will form the rotation?

To say the Red Sox’s rotation was depleted in 2020 would be a huge understatement. With Chris Sale lost for the season due to Tommy John surgery and Eduardo Rodriguez also not throwing a pitch due to myocarditis (inflammation of the heart), the Red Sox spent most of the season with Nathan Eovaldi and Martín Pérez as the only real starters. Roenicke had the unenviable task of filling in the other three spots with a combination of openers and bullpen games. By season’s end, the team’s No. 10 prospect as rated by MLB Pipeline -- righty Tanner Houck -- turned in three stellar outings. Nick Pivetta, the 27-year-old righty acquired in the Brandon Workman-Heath Hembree trade, was impressive in two late-season starts.

In a best-case scenario, Sale will return by June and be back to his vintage self. Rodriguez could be ready by the start of Spring Training, but the Red Sox acknowledge he is coming off an unprecedented health matter for a pitcher. The club holds a $6.25 million option on Pérez, which seems like a no-brainer given his mostly solid body of work in 2020. Eovaldi is on the books for another two seasons and pitched brilliantly late in the season. Expect Bloom to deepen his rotation. The question is whether he would make a major splash and try to sign a free agent like Trevor Bauer. Stay tuned.

3) Will JBJ come back?

For the last seven years, the Red Sox have had the comfort of knowing they had an elite defender in center field -- one who was also a threat at the plate at times. Now, they face uncertainty. Jackie Bradley Jr. is headed to free agency for the first time in his career, and he’s made it clear he will explore his options. As a Virginia native, Bradley could look for a landing spot closer to home.

If Bradley departs, Alex Verdugo certainly has the ability to slide over to center field. But that would leave a sizable void in right field. Fenway Park has a very challenging patch of ground to cover in both center and right, so the Red Sox always preferred to have two plus defenders at those spots. The challenge would get harder if Bradley isn’t re-signed.

4) Can Benintendi rebound?

Left fielder Andrew Benintendi’s swing was almost unrecognizable (4-for-39) before he was lost to the season due to a strained right ribcage. He looked solid at the plate in both Spring Training and Summer Camp, which made his shaky start so surprising.

In his last 827 plate appearances dating back to Aug. 14, 2018, Benintendi has a disappointing line of .256/.335/.396 with 14 homers and 86 RBIs. That said, Benintendi is still young. Next season will be his age-27 season.

“This guy has great all-around ability. It's just unfortunate how the year started,” said Bloom. “He actually looked great in Summer Camp, and then for whatever reason when the season opened he wasn't firing on all cylinders, had a couple of bad weeks and then got hurt. So I wouldn't let that change anyone's mind. This is a guy who has shown the ability to perform at a really high level including in some really critical situations. Still young. Still has all that ability. It's just a shame his year kind of got wiped out.”

5) Who’s on second?

Dustin Pedroia, other than an assorted game here or there, essentially hasn’t played for the Red Sox for the last three seasons due to his troublesome left knee. Pedroia still has one year left on his contract, but nobody seems to expect he will play again.

During Pedroia’s lengthy absence, the team has been unable to find a second baseman with staying power. That’s what makes Christian Arroyo’s finish to the season so intriguing. Arroyo was a first-round pick by the Giants in the 2013 Draft but has been most limited by inconsistency and injuries in his career. But in his late-season cameo for Boston, Arroyo looked excellent on defense and showed some glimpses at the plate, clocking three home runs in his final 11 games.

It would take a leap of faith for the Sox to just hand the job to Arroyo in Spring Training, so look for some competition to be brought in. Michael Chavis had a disappointing season at the plate, but he could also be part of the solution at second.