On Monday, the Red Sox (89-73) held their annual end of season press conference, with manager Alex Cora, chief baseball officer Craig Breslow and team president Sam Kennedy all on stage to answer questions from the assembled local media.

After a disappointing exit in the Wild Card round at the hands of the Yankees (94-68) - a team now with +1500 odds to win the World Series down 2-0 in the ALDS - Boston’s front office is faced with a bevy of questions as they look ahead to 2026.

The organization was finally able to get over the hump and return to postseason play for the first time since 2021. That’s great! But now it’s time for one of the only real name-brands in all of baseball to start competing like the blue blood they are again.

The Red Sox have all the ability in the world to field a World Series-caliber team every single year.

What will they do this offseason to get themselves back into that echelon for 2026?

Two decisions currently out of their hands belong to third baseman Alex Bregman and shortstop Trevor Story, with both players having the ability to opt out of their current deals this offseason.

My Roundtable colleague Brady Farkas put it best when writing about Bregman and Story for the website on Friday afternoon.

Here’s a sampling, but I encourage you to check out the full piece:

“[Trevor] Story signed a six-year deal before the 2022 season. Though he spent much of the first three years hurt, he rebounded in a big way this season, hitting .263 with 25 home runs, 96 RBIs and 31 stolen bases. He's got two years and $50 million guaranteed on his deal. At 32 years old, does he think he can get one more contract that is bigger than that, or does he want to take the sure money?

“Bregman signed a three-year, $120 million last offseason, but he has opt-outs after each of the first two seasons. Two years and $80 million is hard to walk away from, but he could be looking at a bigger deal on the market after his .273, 18-homer season. He's 31 years old, almost 32, and has been to the playoffs nine times in 10 years.”

There are strong arguments to be made for both keeping Story and Bregman, as well as letting either player walk.

Story Pros - He was arguably your Team MVP this season, showing both durability and consistency after a slow start to the season

Story Cons - You got the best possible version of the player, and he will regress back to who he’s been most of his time in Boston, with injury concerns constantly looming

Bregman Pros - He gave you an All-Star level performance for most of the season, both at the plate and in the field, and was easily the leader in the clubhouse on every level

Bregman Cons - His performance waned down the stretch, and he missed a big chunk of the season with a quad injury. As he climbs in age, the juice might not be worth the squeeze

The entire fate of the left side of the infield completely hangs in the balance in the wake of key forthcoming decisions for both players.

And on Monday, Breslow gave us zero insight into where things stand with either player.

Here’s everything Craig Breslow had to say about Trevor Story and Alex Bregman:

Question: Do you expect to approach Bregman and [Scott] Boras in the next month before free agency, and before the opt out decision about a new contract?

Craig Breslow: “You know, I think best to keep those conversations internal. Obviously, Alex has the right, as structured in his contract, to opt out. And he's going to do what's best for his family.

“At the same time, I will not miss an opportunity to talk about his contributions on the field, in the clubhouse, to the coaching staff, to the front office. Every conversation we've had, I learned something. I think that impact and influence has rubbed off on his teammates, and by all accounts, he's loved his time in Boston.”

Q: To that end, then what is the significance to the 2026 Red Sox to keeping him?

CB: “We'll let that play out, but the significance would be having a great player, a proven winner, a strong defender, someone who fits this park really well on our roster.”

Q: When you look at his decision and Trevor's decision, have they given you any indication on which way they're leaning at this point?

CB: “I have not had the chance to draw conclusions about those things. Those are obviously decisions for them to make. At this time, I think everyone will say that they were focused on trying to do everything we could to advance in the postseason.”

Q: Alex’s stats pre-injury and post-injury were dramatically different. How do you quantify that, going to the offseason and trying to figure out what he is?

CB: “Yeah, look - I think Alex did everything he could to get back on the field as soon as possible, including playing before he was 100%. And that deserves a ton of appreciation, because he knew what was at stake, and he knew his role on the team. And we were a better team with Alex at 80% of his sprint-speed than we are without him at all.

“Did that have an impact on his performance? Probably a better question for Alex. But our medical staff, Alex and [Cora] had a great plan to keep him on the field as much as we possibly could, and we were able to execute on that successfully.”

Stay locked in to Roundtable as the story surrounding Story (no pun intended) and Bregman develops.

Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.