Imagine, on New Year’s Day at the turn of the millennium, being told how the next quarter-century would unfold for the Boston Red Sox.

Would you believe it?

Would you believe the team would soon be sold? How about Aaron Boone in ’03? Or the Red Sox finally reversing the 86-year Curse of the Bambino in ’04? Three more championships after that? David Ortiz?

Would you believe the Red Sox would make another Babe Ruth-esque trade, almost exactly a century later, in Mookie Betts? That there would be a 60-game 2020 season due to a global pandemic? Or how Rafael Devers’ Boston tenure would end? No one would have believed that last January, much less 25 years ago when he was 4 years old.

How about the number of managers (nine, including Alex Cora’s two stints) and top baseball operations executives the Red Sox would cycle through?

Trying to predict a quarter-century of anything is impossible, but especially baseball, which is so marvelously unpredictable.

Yet, at the start of a new quarter-century, the Herald’s Red Sox reporters, Gabrielle Starr and Mac Cerullo, are here to attempt just that.

STARR’S PREDICTIONS
Top-level turnover

In the last quarter-century, the Red Sox were led by seven general managers, two chief baseball officers, including current boss Craig Breslow, and one president of baseball operations.

Do with that precedent what you will.

A sale of the team

One thing that makes the last quarter-century of Red Sox history so fascinating is current ownership’s meteoric rise and subsequent self-defenestration from grace.

When principal owner John Henry and his partners purchased the Boston ball club in ’02, they proved themselves unusually committed to the venture.

The most stunning impact was in October, which for over eight decades had been the most heartbreaking month for Boston baseball.

Upon arrival, the first non-Yawkey family Red Sox ownership since the 1930s asked a fan base that had learned to expect nothing but tragedy to believe in magic. And then their teams made magic. With World Series wins in ’04, ’07, ’13 and ’18, the Red Sox have the most championships in the league this century.

Perception and reality have certainly changed since that last trophy, but will Fenway Sports Group ever actually sell the goose that has laid them so many golden eggs?

When profiled by the Financial Times in June ’24, Henry said, “We are committed to the city, the region. So the Sox are not going to come up for sale. We generally don’t sell assets.”

It’s a far cry from the message he gave reporters for Red Sox fans in January ’02, when the sale was approved: “Baseball runs in our veins, just like it runs in yours.”

But it’s unlikely this ‘asset’ will be sold any time soon.

Decision time for Fenway Park

Many will hate this one – myself included – but it’s impossible to ignore.

Fenway will not stand forever. It may have been one of the first steel-and-concrete ballparks in the majors and therefore quite innovative for its time, but with all due respect to Osborn Engineering – the engineering firm that built Fenway and several other ballparks and is still a top sports architecture firm – it’s definitely not as durable as the Parthenon or Colosseum (the one in Rome, not Oakland).

At spring training ’11, after the Red Sox completed a decade-long, $285 million Fenway renovation and refurbishment project, then-team president Larry Lucchino, who passed away in April ’24, told reporters, “If you’re waiting for a new ballpark you’re going to be waiting for a long time.”

FSG has continued to commit millions to further preservation and modernization of the little emerald cathedral.

Yet much like anti-aging skincare, there is only so much anyone can do to delay the inevitable. In 2009, Lucchino told reporters that architects and engineers assured ownership Fenway would be usable for “the next 40 to 50 years.”

You do the math.

CERULLO’S PREDICTIONS
All-Star Game returns to Fenway

This one is probably a lay-up. It’s been nearly three decades since Fenway Park last hosted an All-Star Game in 1999, and it shouldn’t be much longer before the Midsummer Classic returns.

As it stands the All-Star Game will be held in Philadelphia this summer and Chicago’s Wrigley Field in 2027. Beyond that Toronto and Baltimore have each waited longer than Boston and at some point MLB will likely want to showcase the forthcoming new ballparks in Las Vegas and Tampa Bay once those open.

But Fenway’s time should be coming soon, and it would make a lot of sense to bring the All-Star Game back once the Fenway Corners redevelopment project surrounding the ballpark is finished by the end of the decade. That work will complete the ballpark’s decades-long transformation, which began shortly after the last All-Star Game in 1999 following Fenway Sports Group’s purchase of the franchise in 2002.

My guess is Boston will get its next game in 2029, which would coincide with the 30th anniversary of the last All-Star Game.

Sox win World Series within next 10 years

Under the club’s ownership the Red Sox have averaged two championships per decade. Obviously Red Sox fans know better than anyone that nothing is guaranteed and long droughts are possible, but coming out of a five-year rebuild the club looks as well positioned over the next few years as anyone outside of the Dodgers.

Obviously we’ll see what the future holds, but if the club’s young core continues to develop and everyone stays healthy, this group should get a couple of bites at the apple over the next few years.

Anthony has number retired

The Red Sox made a catastrophic mistake letting Betts suit up for another team. To their credit they learned from that mistake and made sure not to repeat it with Roman Anthony.

Anthony has the makings of a superstar, and with his contract extension he’ll remain under club control in Boston through 2034. That’s essentially a whole decade to write his story at Fenway Park, and if he reaches his full potential then it wouldn’t be a shock to see his No. 19 one day adorn the right field deck alongside Ted Williams, Pedro Martinez, David Ortiz and the rest of the club’s all-time greats.

Will Anthony spend his entire career in Boston? We can worry about the back half of his career later, but barring unforeseen circumstances he’ll be one of the defining players of this next quarter-century, and that’s something Red Sox everywhere should look forward to.