The most challenging offseason in recent Boston Red Sox history technically began Monday, but given the team’s struggles in 2019, the defending World Series champions got a head-start on things.

The Red Sox fell out of contention in August and September, allowing them to turn their focus to an offseason that could be littered with change. Red Sox ownership stated last week the goal is to get the payroll under Major League Baseball’s competitive balance tax, an initiative that coincides with difficult decisions about two of the club’s biggest offensive threats.

J.D. Martinez and Mookie Betts undoubtedly will be the focal points of the offseason for the Red Sox. The club officially will learn in the five days following the World Series whether Martinez will opt out of his contract, while Betts’ lingering contract status — he can hit the open market next winter — means another tough decision is on the horizon.

Can the Red Sox somehow retain both Martinez and Betts for the long term while also getting under the CBT? It’s possible, Sox president and CEO Sam Kennedy said Monday, but it won’t be easy.

“There is a way, but obviously it will be difficult given the nature of the agreements and the contracts we have in place,” Kennedy said Monday at Fenway Park. “We have a very targeted and strategic plan that we’re building now. Some of the dates related to contract decisions come right after the World Series. So we’ve had some time in September to focus on the offseason given where we were in the standings. It is going to be a challenging offseason, but we’re ready to attack it head-on and do everything we can to put a competitive team out there not just for next year but 2021, 2022.”

With Martinez, Kennedy acknowledged the Red Sox are in wait-and-see mode, admitting the club hasn’t engaged in any “specific discussions” with the designated hitter/outfielder. The situation regarding Betts is a little less defined. The 2020 season is the final year of Betts’ first contract, and obviously the two sides haven’t been able to find common ground on a long-term extension. Betts and his representation seem hellbent on reaching free agency, meaning the Red Sox might have to blow away the Betts camp with a huge offer to keep in him Boston for the long term. Of course, that would appear to run counter to getting the club under the CBT — even if Martinez leaves.

“It’s not frustrating because I think it speaks to Mookie’s confidence and how special of a player he is,” Kennedy said. “He really does love it here. He told me he loves it here. He told (senior vice president of baseball operations) Raquel Ferreira he loves it here. He told (manager Alex Cora) he loves it here. You can see with the joy and energy and enthusiasm in which he approaches playing baseball at Fenway Park — the fans love him.”

Kennedy acknowledged the goal is to reduce payroll but that it isn’t a hard-and-fast mandate.

“John (Henry) said there is a goal to try to get under the CBT in 2020. But he also said, and Tom (Werner) followed up and clarified, that that’s a goal and not a mandate,” Kennedy said. “We spent some time over the weekend as a group with the baseball ops transition team about different scenarios where you can see the possibility if there are strategic decisions that would cause us to go over that could be a possibility.”

Finding a way to keep both Betts and Martinez long term seems like it would fall under those “strategic decisions,” but that’s easier said than done at this point.

Thumbnail photo via Raj Mehta/USA TODAY Sports