Revisiting Potential Red Sox Direction After Jordan Montgomery Decision

The Boston Red Sox entered the offseason with the potential to spend big on free-agent pitchers to upgrade the rotation and set up the chance for contention in 2024.

The lone addition ended up being Lucas Giolito, who had previously been as durable as any starter in the league before suffering a season-ending elbow injury. The final chance for an impact signing vanished when Jordan Montgomery reportedly signed with the Arizona Diamondbacks on Tuesday night.

The developments of the offseason make comments from Red Sox president Sam Kennedy’s availability at Winter Weekend worthy of revisiting.

“We didn’t match up on a couple of the high-profile free-agent pitchers,” Kennedy told reporters at MassMutual Center back in January. “… Excited about Craig Breslow’s ability to identify pitching and develop pitching and institute pitching infrastructure that will help get us there. We recognize that we haven’t matched up on the big name, high-profile free agents. We’re gonna let the build of our team sort of dictate what we do as we go forward.”

The Red Sox are in an interesting position with the offseason basically over with the calendar nearly ready to flip to April. Boston has talent at the big-league level and will certainly take a step forward when its next wave of talent makes the leap from the minor leagues.

“We’re going to stay disciplined with this approach to make sure we have this growing core of young players,” Kennedy added. “That’s really important because we think that’s going to position us for the best chance to be successful for the long term.”

Kennedy added: “We’ve always had success when we’ve had a core of young, homegrown, talented players matched up with high-profile free agents. Impact players that come from outside of the organization. That is something that will not change. That said, we have not matched up this offseason. We recognize that. The philosophy has not changed. We need to have a robust (core) of homegrown, talented players. There will be a day where we match up again on a high-profile free-agent deal. It hasn’t happened this offseason.”

That seems like a simple message to understand on paper: when the young core is ready for the push to the finish line, spending will make sense. That was the message in January and is ready for context with Opening Day for the 2024 season just two days away.

So, what will it take to reach that point for the Red Sox?

Some of the young building blocks have already cemented their roles at the big-league level, from first baseman Triston Casas slugging in the middle of the Red Sox order to Brayan Bello eating innings in the rotation. Jarren Duran remains youthful as a sparkplug at the top of the order. With that base to build on, the timetable for prospects such as Kyle Teel, Roman Anthony and Marcelo Mayer being able to soar becomes that much more important. The realistic scenario is that one of those three could debut in 2024 and the goal is for the entire trio to be in Boston to start the 2025 season.

If the established big-leaguers keep improving and the “Big Three” prospects can reach Fenway Park by then, will that be the phase of the build that would enact spending habits of the past that have assembled championship teams for the Red Sox?

The future investment in free agency, particularly with a strong class next winter, could be on the line this season. Based on the messages of ownership, it’s up to the top trio of Red Sox prospects along with the big-league core to overamplify that the team is ready for its next splash addition on a championship path.