Triston Casas is one of the young stars Boston should think about giving a contract extension to before the price to keep him becomes something the team is not willing to pay. Reed Hoffmann/Associated Press

BOSTON — With Boston Red Sox pitchers and catchers reporting to Fort Myers, Florida, in just two weeks, let’s take a look at some questions surrounding the team:

1. When will the Red Sox begin extending their young stars?

Over the last several years, members of Red Sox leadership have expressed regret about their failure to extend homegrown stars earlier in their years of club control. Perhaps Mookie Betts would still be in Boston. They probably would have saved at least $50 million on Rafael Devers if they hadn’t waited until his final year of arbitration.

Concurrently, the Atlanta Braves put together an interesting model for building a perennial contender. Since 2019 they’ve committed at least $735 million – $895 million including all options – among seven contract extensions for a young core that includes five members of the 2023 All-MLB team: Ronald Acuña Jr., Austin Riley, Spencer Strider, Matt Olson and Ozzie Albies. Olson, Riley and Acuña Jr. also took home Silver Slugger Awards, and Acuña Jr. is the reigning NL MVP. His eight-year, $100 million deal, which can go up to 10 years, $134 million, now looks like the steal of the decade.

Other teams are beginning to follow suit. On Sunday, the Tigers announced that they signed Colten Keith to a six-year extension through the ’29 season with club options for the following three years and approximately $15 million in escalators. The infielder has yet to make his major league debut, but is expected to be Detroit’s Opening Day second baseman.

Extending a player before their first big-league game is a significant risk – Scott Kingery didn’t pay off for the Philadelphia Phillies – but what about someone like Triston Casas, who just finished his first full season in the majors as a Rookie of the Year finalist? At Winter Weekend, Werner answered “absolutely” when asked if the Red Sox plan to try and lock in young players earlier. They might be waiting out a bridge year, but shouldn’t wait too long to lock up their brightest stars. Not again.


Angels Rangers Baseball

Jordan Montgomery, who helped the Rangers win the World Series, is still available as a free agent. He has ties to Boston and would be a good fit with the Red Sox. Tony Gutierrez/Associated Press

2. Why won’t the Red Sox go for Jordan Montgomery?

Jordan Montgomery remains a free agent and the Red Sox remain unwilling to take the plunge.

“It’s almost inexplicable the Red Sox are not seizing the moment,” wrote The Athletic’s Ken Rosenthal. “The Red Sox, though, continue to show little inclination to spend big.”

Why not? A frontline starter has been Boston’s obvious need since Day 1 of the offseason. Their financial commitments or lack thereof are public knowledge, and there’s nothing stopping them from giving out a deferral-heavy deal, either; the Los Angeles Dodgers already shattered the mold with Shohei Ohtani’s unprecedented contract.

Montgomery is a reigning World Series champion with years of American League East experience. His wife, McKenzie, is doing her dermatology residency at a Boston area hospital, so they probably would welcome an offer from the local baseball team.

The Red Sox shouldn’t be treading water if they truly expect top prospects such as Roman Anthony, Kyle Teel and Marcelo Mayer to arrive within the next two seasons. There’s little elite starting pitching talent in the upper levels of the minors; the front office should be building a rotation to complement their burgeoning core.


3. What will this year’s 2004 20th anniversary celebrations look like without Tim Wakefield?

That Tim Wakefield died at 57 the year before the 20th anniversary of the historic 2004 season is unbelievably sad and unfair. The celebrations sure to come this year will be bittersweet without the knuckleballer, who endured the ultimate heartbreak in Game 7 of the ’03 ALCS, and was redeemed when the Red Sox finally overcame the Yankees the following October.

How will the Red Sox honor him? Will the team wear No. 49 patches this season? Will the number be retired altogether? The club has been tightlipped about specifics, but Werner pointed to the April 9 home opener, or 4/9, as a notable day in this regard.

4. Will Curt Schilling be invited?

Curt Schilling’s inclusion in ’04 anniversary celebrations was already in jeopardy before he made both Tim and Stacy Wakefield’s cancer diagnoses public days before his former teammate’s death.

To make matters worse, Schilling admitted he didn’t have their permission to reveal their situation, and he didn’t know if they wanted people to know. The Red Sox, the Wakefields’ loved ones, and fans were outraged.


Schilling has yet to publicly apologize or make any statement. He’s been embroiled in countless controversies over the years but none were a bridge too far in the eyes of people who believe in a strict separation of on- and off-field behavior. His treatment of the Wakefields seems to have destroyed any remaining goodwill he had in Boston.

Sam Kennedy, the team president and CEO. declined to answer when asked if Schilling would be included in any ’04 festivities in the end-of-year press conference, but it’s unfathomable that Schilling could be celebrated at Fenway. If the Red Sox want to honor Wakefield, not inviting the person who brought him so much pain in his final days is an obvious way to start.


5. How will Dr. James Andrews’ retirement impact sports?

If one were to list the most influential figures in the last half-century of sports, a doctor probably wouldn’t immediately come to mind. (Well, perhaps Julius “Dr. J” Erving.)

Dr. James Andrews, who made one of the most significant contributions in sports history, announced his retirement last week.

It’s impossible to measure the impact of a man who revolutionized sports medicine, and treated everyone from Michael Jordan, to Bo Jackson, to Tom Brady and Drew Brees.


In recent years, Andrews worked with Chris Sale, David Price, Christian Vázquez, Josh Beckett and Clay Buchholz, but his Red Sox ties date back nearly 40 years. In 1985 he used arthroscopic surgery, still a relatively new method, to repair a second-year pitcher’s previously undiagnosed torn labrum, and devised a rehab program. Roger Clemens went on to have a decorated career, and because he raved about Andrews to every athlete he met, the doctor became sports stars’ go-to.

Where would sports medicine be without Andrews?

6. Are the Red Sox setting themselves up for trouble with top prospects?

With little active-player star power in attendance at Winter Weekend, the Red Sox put their top prospects under a bright spotlight.

Will the front office’s effusive praise and focus on Mayer, Teel and Anthony come back to bite them? Expectations are already through the roof; proclaiming them as the harbingers of contention only ups the immense pressure.

7. Will anyone show up for Truck Day?

Truck Day is next Monday.

In previous years, fans would show up at Fenway Park to send the equipment truck on its annual journey to Fort Myers, Florida. The way this offseason is going though, there seems little enthusiasm to spare.

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