Congratulations on making it through the first full week of what is sure to be a very long Red Sox offseason.
Here are seven questions to ponder going into Week 2:
1. How can the Red Sox improve internally?
The Red Sox have relied heavily on internal development in recent years, and chief baseball officer Craig Breslow suggested at this week’s end-of-season press conference that they will continue the practice going into 2027.
“There are a lot of reasons to believe that the existing offense should be better,” Breslow said, pointing to the months-long injuries that sidelined outfielder Roman Anthony, shortstop Trevor Story and infielder Curtis Mead, who suffered a season-ending wrist fracture in his second Red Sox at-bat.
Maybe Breslow is right. But there are also plenty of indicators that the existing offense isn’t enough even at peak health. Such as the fact that even though over half a dozen Red Sox players hit career-highs in home runs this year, they still ranked fourth-worst in the American League in the metric.
But the additional wrinkle this offseason is the impending lockout when the collective bargaining agreement between Major League Baseball and the Players Association expires on Dec. 1. The Red Sox won’t be able to contact any of their players (or make big-league free-agent signings or trades) if the two sides don’t come to an agreement before then. This means no check-ins with Anthony, to see if his hand is improving, or left-hander Garrett Crochet, to find out if he is having a normal offseason as expected.
2. Will the Red Sox be aggressive before potential MLB lockout?
The Red Sox will have roughly one month between the end of the World Series and the CBA expiration in which to act. But will they?
They were not among the teams that combined for an eye-popping $1.4 billion in contractual commitments on the last day before the 2021-22 lockout began, headlined by the Texas Rangers’ blockbuster signings of shortstop Corey Seager (10 years, $325 million) and second baseman Marcus Semien (seven years, $175 million).
Though the Red Sox were technically in rebuild mode at the time, they were also coming off a deep playoff run. They had every reason to try to build on that unexpected success, yet their only pre-lockout moves were trading Hunter Renfroe to the Milwaukee Brewers for Jackie Bradley Jr, and signing veteran pitchers Rich Hill, Michael Wacha and James Paxton as he recovered from Tommy John surgery.
The free-agent pool was also significantly stronger last time around. It will be interesting to see if the dearth of bat power on this year’s market makes the Red Sox more aggressive or even more willing to stand pat than usual.
3. Should MLB shorten the regular season, expand the playoffs, and introduce re-seeding and opponent selection?
Let’s set aside the salary cap for the purpose of this question, because as the union’s public statement noted Thursday, it’s a non-starter: “Unfortunately, the league once again made clear that all of its proposals are contingent on players’ agreement to a salary cap, a system that guts player rights and compensation, as well as its other anti-player proposals.”
MLB this week proposed shortening the regular season from 162 to 154 games, the typical length of the season between 1904-61. Doing so would allow for a weekly Monday off-day, as is customary in the minor leagues. This change would be implemented in 2029.
The league also wants to turn the divisional round from best-of-five to best-of-seven, like the pennant round and World Series.
Now, here’s the weird one: Opponent selection. Starting next year, the highest-seeded teams in the wild card and divisional rounds would be allowed to choose their opponents.
“Allowing the top seeds to select their opponents in the first rounds would create compelling storylines, intensify existing rivalries and create new ones,” MLB spokesman Glen Caplin said in a statement.
Many baseball fans decried this particular item online, and it’s a no for me as well. In addition to the potential for humiliation and calamity should a team choose and lose, this pick-your-poison setup has a gimmicky, manufactured quality.
And it’s wholly unnecessary when baseball spawns these moments organically. Remember the 2018 postseason when Yankees fans chanted “we want Boston” as their team defeated the then-Oakland Athletics in the then-one-game wild card at Yankee Stadium to advance to face the Red Sox in the American League Division Series?
It was real October theater. Aaron Judge blasted “New York, New York” on a speaker as he walked out of Fenway Park after the Yankees took Game 2. Boston responded by winning the next one by a mere 15 runs in the Bronx.
This game is pretty darn compelling as is, without engineered scenarios and constant changes. The league would do well to remember that as it prepares to bring all the growth and enjoyment of the last four years to a screeching halt.
4. What is the best MLB postseason format?
I liked the original one-team Wild Card era (1995-2011), and the two wild cards with a win-or-go-home playoff game (2012-19, ‘21). The latter was particularly thrilling, high-stakes entertainment.
The current format, not so much. That a team can win its division and still have to play in a three-game wild card round is nonsensical.
MLB would never go for this, as they proposed a 14-team playoff format last time before they settled for 12 teams, but I’d like to return to the two-team wild card format and expand it from one game to best of three or five. It would ensure all three division winners get a bye, and shrinking the number of playoff spots would make the regular season more competitive again.
5. How strict are the lockout rules?
Remember how MLB scrubbed all player images and videos from official team and league websites during the last lockout? Get ready for round two this winter.
But the lockout guidelines are far more specific and complex, as outlined in the 34-page memo the league distributed to team owners and executives at the start of the month.
Avoiding players “to the greatest extent possible” is one of several directives. Team employees “should be cordial,” but not discuss baseball if they come across a player in the wild. Likewise if they are attending a player’s wedding.
Another? No holiday cards to players after Dec. 1. Talk about giving the Grinch a run for his money.
6. What have the Yankees become?
This Bostonian certainly is not complaining about the Yankees getting swept out of the playoffs by the Tampa Bay Rays, or their lack of World Series championships since 2009. But the world seems somewhat off-kilter in this era in which making the postseason is enough for the 27-time champions.
As an early-90s baby, I’m old enough to remember how longtime Yankees owner George Steinbrenner ran his team. He would’ve fired someone by now. Probably multiple people.
Instead, Hal Steinbrenner’s Yankees are expected to re-sign longtime general manager Brian Cashman, who will then retain manager Aaron Boone.
Again, no complaints. It’s just a bit baffling.
7. Was the 2026 Red Sox season a success?
My Herald co-reporter Mac Cerullo and I debated this question earlier this week, and we want to know what you think. My inbox awaits your answers.