With the Roman Anthony extension, the Red Sox could enter the empire business

Amid the darkness of a cool, crisp, and electric October evening in 2003, the most memorable moment of one of the most memorable games in MLB history stabbed New Englanders in the heart shortly after midnight. It was somehow both shocking and predictable all at the same time.

Aaron Boone’s moonshot launched off Tim Wakefield’s knuckleball in the bottom of the 11th inning of Game 7 of the ALCS wasn’t just about what happened that night, or even in that series. It was so much bigger. It was the latest in a relentlessly long line of stomach turning defeats. It further strengthened the notion that the Red Sox were never going to beat the Yankees when it mattered, and that Boston would always be defined by its curse.

But with the benefit of hindsight, we now know this moment wasn’t a new pillar further entrenching a reality destined to stay in place forever, but rather, the last gasp of a seemingly stable status quo. Instead of the bedlam in New York that night signaling a continuation of the 1920-2003 baseball world order, it alternatively served as a catalyst for massive upheaval. Over the next twelve months, the Red Sox matched the Yankees in an epic arms race, and the following fall (as we all know), they toppled the empire that had squashed them for so long.

Now, with the benefit of ever more hindsight, this period in Red Sox history somehow keeps getting better, because in addition to the Red Sox spending 2004 finally taking down the Yankees, something else extremely important happened: Roman Anthony was born.

For as far back as anybody can remember, the Red Sox have been as much about their past as they have their future. They play at the oldest ballpark in major North American sports, their curse followed them around like a shadow for eight and a half decades, and despite some pretty dramatic changes between 2004 and 2018, everything always felt connected back to their biggest and most important championship from that era, particularly through 2016 while David Ortiz was still suiting it up.

But all of that is starting to change. After losing their way, failing to make the playoffs five times in six seasons, botching the bad campaigns so embarrassingly they finished in last place of six times, and a new core slowly starting to emerge from the ashes in 2025, the Red Sox feel as much about their compelling future right now as they do their compelling past. For the first time, there’s a solid buffer between the post 2004 party that lasted through the 2018 championship season and wherever we’re headed now, and that’s exciting!

To put a microscope on it, this brand of excitement is different. Something I haven’t experienced as a Red Sox fan before. Not solely because of Roman Anthony, but rather because he’s entering the scene as part of a large, collective core that includes Garrett Crochet, Ceddanne Rafaela, Brayan Bello, Marcelo Mayer, Kristian Campbell, and hopefully more guys joining from Worcester soon.

If it all goes right though, Roman Anthony will become the leader and frontline man of the group. He oozes maturity, superstar potential, nerd stat upside, a love of Boston, and early indications of being able to handle clutch at-bats. When you put it all together, he just has a general aura about him. And now, with a near decade long extension complete, every important conversation about Roman Anthony becomes entirely about baseball! No more service time talks, no more worrying about going year to year on a contract, no agonizing about if he’s going to go down the same road as Mookie Betts. He’s here, he’s ours, and he’s wonderful!

But of course, one guy doesn’t make a championship contender. The two greatest hitters of the last 90 years (Ted Williams and Barry Bonds) have a combined zero World Series titles between them. What makes the Roman Anthony extension so special is that it comes in the middle of the Sox locking up and promoting other guys as well. He’s not just a young potential superstar, he’s a young potential superstar with a young supporting cast that’s likely to stay together for years, and surprisingly, even with all their post 2004 success, this is something the Red Sox just haven’t had in decades.

To further illustrate this point, let’s take a look at the top ten players by rWAR (baseball reference WAR) of the four modern Red Sox World Series teams.

There are 40 names listed there, and 36 of them are different. Ortiz obviously appears the most (three times), and then there’s Dustin Pedroia and Curt Schilling each appearing twice, but other than that, there’s no carry over. In fact, the 2018 squad has zero carry over from the 2013 group listed here. This is incredibly rare for a franchise winning four World Series titles in a 15 year span. Pretty much any other example of that kind of success over that short a period of time is going to include more connective tissue between the championships.

Amazingly, the Red Sox managed to knock it down and build it back up three separates times after 2004 in just a 15 year period after not being able to do it once for 86 years. Baseball remains weird, wild and beautiful!

But now, as we leave that era behind for good, look at where the current situation is leading us. Despite all the losing in recent seasons, the Red Sox still find themselves with more championships than any other team in MLB so far this century. It’s the same place they found themselves in 100 years ago before they sold the best player in the sport and paid for it by handing the team of the century title off to the Yankees. Almost unbelievably, they might have done a smaller version of that by trading Mookie Betts off to the Dodgers in 2020, but we’ll have to wait and see how that plays out.

What is very different this time however is what the Sox are building in the years following the awful trade. The post-Babe Ruth Red Sox didn’t have a winning season again until 1935. These Red Sox seem on the verge of being legit contenders for years to come with the current core they’re locking up. Furthermore, and this is where it matters for the modern fan, we’re not just talking about being good most years and having a chance to win multiple World Series titles like they did from 2004 to 2018, but rather being good with the same sustainable group of guys that will be there year in and year out.

In other words, they have a future.

And with that future comes some pretty enormous stakes.

About midway through the greatest season of the greatest show ever created, Jesse Pinkman asks an arrogant Walter White if he’s in the meth business or the money making business. Overlooking the morality of the situation, Red Sox fans should be asking John Henry the same general question. John, are you in the baseball business, or the money making business?

Unfortunately, the answer at this point in his tenure is probably more the second option, and that’s a real shame because to quote Walter White from that season, “there’s gold in the streets just waiting for somebody to come pick it up.” If the Red Sox start behaving like a major market club again and add a huge spending element to this core, the ceiling becomes a dynasty. And if you stack a dynasty on top of the four championships they already have since they got walked off on that fateful night in 2003, you’re all of a sudden starting to carve out the inside track for becoming the team of the century.

This is a chance to build on 2004 and expand the legacy of this franchise in a way we never could have dreamed of a quarter of a century ago. While the first major component of 2004 was always going to be putting away the ghosts, avenging fans who spent a lifetime rooting for the Red Sox without ever seeing them win a World Series, and finally punching the Yankees in the face, it now also has a chance to be something else. A chance to build a new empire where the other one stood.

For so long, 2004 has rightfully been about the end of something. The greatest conclusion to one of the greatest sports stories ever told. But if the man born that year ends up becoming a superstar face of the franchise amid a core that’s then repeatedly supplemented with top of the line talent, then we unlock an entirely new reality. If it all goes right, then by the time Roman Anthony’s career is over, most Red Sox fans won’t look at 2004 as a perfect ending to a century long story, but rather, a perfect beginning to it.

And so, if John Henry was asked right now if he’s in the baseball business or the money making business, I hope he’d have Walter White’s ultimate response: “Neither. I’m in the empire business.”