Boston Red Sox

The problem, obviously, is that there are far more questions than answers – and the clock is already ticking. The Red Sox have now finished last twice in three years, five times in the last 11. They are 194-190 over the last three seasons and 278-268 over the last four, and we all know the oldest truth.

If you’re not getting better, you’re getting worse.

As such, the rest of the American League East (and then some) has passed them by.

Above all else, here are the biggest and most frequent questions Red Sox fans have asked these last several months: what is the direction of the franchise? Where is this all going? And the answer: we don’t know. And that uncertainty is extremely unsettling, which makes the next 3-6 months one of the more pivotal times of the John Henry-Tom Werner ownership era.

Over the last couple of days, Red Sox officials answered an array of questions regarding the many questions facing the team. Here are the unanswered ones that should concern you the most.

  • Are Sox leaders all on the same page?

    BOSTON, MASSACHUSETTS - AUGUST 23: Boston Red Sox manager Alex Cora looks on during the third inning at Fenway Park on August 23, 2022 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)

    BOSTON, MASSACHUSETTS – AUGUST 23: Boston Red Sox manager Alex Cora looks on during the third inning at Fenway Park on August 23, 2022 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)

    I’ve said this a million times and I’ll say it again: the most important relationship in the organization is the one between the manager and the general manager or chief baseball officer, in this case Alex Cora and Chaim Bloom. Cora’s comments before Game 162 spoke volumes about he felt about the season and the overall decision-making, which left too many holes on the roster and sent too many mixed signals.

    “One of the things that I really want is a sense of urgency. It’s something that, as an organization, we’ve done it throughout the years and we have to push hard in the offseason,” he said. “The message is going to be now. I love the future, we love the past – we don’t like this past (in 2022), right? – but I think that living in the present and pushing hard is something we’re going to talk a lot (about). I think it’s something that, it pushes you to be great. And it’s not that we didn’t do it this year, but I think the message should be louder.”

    We don’t need to rehash everything that took place during the course of the year, but suffice it to say this: it too often felt like the Red Sox in general – or maybe Bloom in particular – were prioritizing the long-term over the short. There has to be a better balance there. The Red Sox aren’t a 4A team. They’re a big league club. Only a limited amount of player development can take place in Boston. In the big leagues, you play to win.

    In Cora’s mind, undoubtedly, this is not what he signed up for. He came to Boston in 2018 to get the Red Sox over the hump. They threw him a lifeline after his suspension in 2020, but he’s paid his debt – and they wanted him back as much as he wanted them. The fact that Cora made the above comment publicly suggests he had expressed the same sentiments behind closed doors. If he hadn’t, there is still a bridge to gap and that should concern you.

  • How big a step can Chaim Bloom take as an executive?

    BOSTON, MASSACHUSETTS - JANUARY 15: Red Sox Chief Baseball Officer Chaim Bloom looks on during a press conference addressing the departure of Alex Cora as manager of the Boston Red Sox at Fenway Park on January 15, 2020 in Boston, Massachusetts. A MLB investigation concluded that Cora was involved in the Houston Astros sign stealing operation in 2017 while he was the bench coach.  (Photo by Maddie Meyer/Getty Images)

    BOSTON, MASSACHUSETTS – JANUARY 15: Red Sox Chief Baseball Officer Chaim Bloom looks on during a press conference addressing the departure of Alex Cora as manager of the Boston Red Sox at Fenway Park on January 15, 2020 in Boston, Massachusetts. A MLB investigation concluded that Cora was involved in the Houston Astros sign stealing operation in 2017 while he was the bench coach. (Photo by Maddie Meyer/Getty Images)

    Let’s make something clear here: just because Bloom came from the Tampa Bay Rays doesn’t mean he built that organization. He was an assistant there. Until now, he’d never run an organization from the top.

    BOSTON, MASSACHUSETTS - JANUARY 15: Red Sox CEO Sam Kennedy looks on during a press conference addressing the departure of Alex Cora as manager of the Boston Red Sox at Fenway Park on January 15, 2020 in Boston, Massachusetts. A MLB investigation concluded that Cora was involved in the Houston Astros sign stealing operation in 2017 while he was the bench coach.  (Photo by Maddie Meyer/Getty Images)

    BOSTON, MASSACHUSETTS – JANUARY 15: Red Sox CEO Sam Kennedy looks on during a press conference addressing the departure of Alex Cora as manager of the Boston Red Sox at Fenway Park on January 15, 2020 in Boston, Massachusetts. A MLB investigation concluded that Cora was involved in the Houston Astros sign stealing operation in 2017 while he was the bench coach. (Photo by Maddie Meyer/Getty Images)

    When Theo Epstein came in as a 28-year-old, he had baseball lifer Bill Lajoie at his side and pit bull Larry Lucchino over his shoulder. Neither was afraid to pull the trigger on a big move and both urged Theo to be bold.

    Bloom was reared in a far more conservative operation – out of necessity – and doesn’t have the same mentors.

    This offseason, the Red Sox have a ton of money to spend. They also have a lot of needs to fill, which means they can’t necessarily buy two big-ticket items and solve their problems. There’s some sort of give-and-take there, which brings us to this comment by Bloom.

    “I would be cautious to put too much into what’s out there on the rumor mill. I mean, the fact of the matter is, in any offseason, we should show interest in a lot more guys than we are ultimately going to end up with. If we don’t do that, we’re not doing our jobs,” he said Thursday. “So when you do that, you’re ultimately going to end up with only a small handful of those players. You just have to make sure you end with the right guys – on the right deals.”

    If those last four words are a little concerning to you, they should be. On the right deals. What does that mean? By definition, deals for superstar players are almost never the right deals. They almost always come with dead money at the end. The way to mitigate that is to keep drafting, keep developing, keep scouring for low-cost options that can offset the big tickets. Bloom is deft at that second part of the job. But healthy, productive stars win on the field and at the ticket window. If Bloom and ownership – and let’s not leave out the men with the money – are afraid of that, well, 26 players making $9.5 million each is only going to get you so far.

  • How integral are Xander Bogaerts and Rafael Devers to any success?

    BOSTON, MA - OCTOBER 5: Xander Bogaerts #2 of the Boston Red Sox tips his cap to the crowd after he is removed from the game the seventh inning against the Tampa Bay Rays at Fenway Park on October 5, 2022 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images)

    BOSTON, MA – OCTOBER 5: Xander Bogaerts #2 of the Boston Red Sox tips his cap to the crowd after he is removed from the game the seventh inning against the Tampa Bay Rays at Fenway Park on October 5, 2022 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images)

    Let’s hit this head on, too: we all love what Bogaerts stands for and there’s an obvious emotional attachment there for everyone. But what if the Red Sox can sign Trea Turner for a little less or move Story to shortstop and become a better team by reinvesting the money elsewhere? If the players win, you’ll love them all. That said, there are obvious questions that come along with playing in Boston – or, for that matter, working in Boston (just ask Bloom) – and so Bogaerts comes with some answers already built-in. But you get the point. Don’t get too hung up on one player. (Just to be clear here, I very much want Bogaerts back and he drips with intangibles.)

    That said, Devers, in particular, feels like an absolute must. He’s young and he bats left-handed, produces for average and power, has generally excelled in big situations. Let’s say he can’t play third base in three years. So what? David Ortiz didn’t play a position, either, and he would have been worth whatever the Red Sox paid him. Relatively speaking, the Sox got Ortiz on the cheap. But no one would have bitched if they paid him more money. Because he won.

    According to Sean McAdam of the Boston Sports Journal, the Sox have already engaged with Bogaerts, which should not surprise you. He is merely the first domino to nudge in an offseason lined with them. Where this all takes the Red Sox is anybody’s guess, but the goals for the Red Sox this offseason are best if kept simple.

    Get on the same page.

    Be bold.

    And do what is best for your team.