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John Henry takes stock of the Red Sox’ present and future

The Red Sox’ present and future await definition.

In the present, the team is a contender but hardly a lock for the postseason. The Sox entered Wednesday with the third-best record in the American League East (47-41) and second-best record in the wild-card race, one-half game behind the Rays and a game in front of the Blue Jays.

But the Mariners, Orioles, and Guardians are all within three games of the Red Sox, suggesting that a playoff spot is a solid possibility but far from assured. While Chris Sale’s return on Tuesday represented the start of a midyear wave of reinforcements that offers cause for optimism, the extremity of the Sox’ struggles (11-22) within their Group of Death division — in which all five teams are at .500 or above — makes clear the challenge.


The future is similarly uncertain. The Red Sox have two homegrown cornerstone players in their primes on the left side of their infield, yet the outlook surrounding whether Xander Bogaerts (eligible to opt out of his six-year, $120 million deal after this season) and Rafael Devers (eligible for free agency after 2023) remains unsettled.

Meanwhile, while the Sox have made significant strides in laying the groundwork for a future homegrown core, that remains a work in progress. What is the overall sense of where the organization sits?

“I feel good, but we’re still in a building mode here. We’re concentrating on building our organization from top to bottom,” principal owner (and Globe owner) John Henry said in a recent interview at Fenway Park. “We took a good step forward last year. We’re taking a good step forward this year. But we’re still building.”

The notion of building, while working toward a fifth title since 2004, is one that suggests change. The Red Sox have not been shy about that proposition, even if it has meant a succession of moves that Henry characterized as “painful.”


The team has traded franchise luminaries Nomar Garciaparra, Manny Ramirez, Jon Lester, and Mookie Betts during the more than 20 years of the ownership group, parting with each when they were within a year of free agency. The trades of Garciaparra, Lester, and Betts followed unsuccessful negotiations on extensions in the year (or years) preceding their arrival on the open market.

The retention — or lack thereof — of star players has been a major talking point throughout John Henry's ownership tenure.Stan Grossfeld/Globe Staff

The Sox have retained other franchise players in that time. Most notably, the team repeatedly re-signed David Ortiz and ensured that others retired as Red Sox after more than a decade in the organization, a group that includes Dustin Pedroia, Jason Varitek, and Tim Wakefield.

Henry characterized the effort to build as one that improves the team’s ability to retain stars, rather than as an acknowledgment of the inevitable departures of homegrown contributors.

“It’s difficult for any team in baseball to keep their team together, especially great teams together, for a long time. It’s very difficult unless you have a really strong organization, a foundation for your organization,” said Henry. “And even then, you have to make tough decisions.”

What does that mean for Bogaerts and Devers? After the Red Sox got nowhere near deals with them in spring training, can they be retained beyond their eligibility for free agency?

“It takes two to make a deal. I think it’s clear both of them want to be here. We want them here,” said Henry. “We made efforts in the past to try to sign players that we weren’t able to sign. It’s not 100 percent our fault when we don’t end up signing a player. We’ve signed players where it’s really worked out. We’ve signed others that, it’s our job to try to sign the right players. Frankly, over the last 20 years, we haven’t done it [every time], so we’ve had to break teams up.


“The key thing I think with a long-term deal is to make it with the right players. For us at this point, both Raffy and Xander are two players we would love to have. In Xander’s case, it could be till the end of his career. But players have rights and you have to respect that.”

In three offseasons under chief baseball officer Chaim Bloom, Trevor Story (six years, $140 million with a player option that would increase it to seven years, $160 million) is the only player the Red Sox have signed to a deal of more than two guaranteed seasons and more than $20 million.

The Story deal features the eighth-largest guarantee to a player in the last three offseasons, yet still is less than half of what the Rangers guaranteed to Corey Seager (10 years, $325 million) and the Yankees guaranteed to Gerrit Cole (nine years, $324 million). Do the Red Sox envision operating at the top of the market?

The Sox invested big money in Trevor Story this winter.Carlin Stiehl for The Boston Globe

“We’ve always spent to some degree on stars,” said Henry. “Do you not consider Story a big free agent signing?”


Indeed, the signing of Story positioned the Red Sox to go past the luxury-tax threshold in 2022 for the first time under Bloom. The team is open to spending more as the trade deadline nears, recognizing an opportunity to build on last year’s surprise run to the ALCS.

That said, Henry noted that spending is not limited to player payroll, and that the process of building the organization has involved investments in baseball operations that are critical even if more difficult to see.

“The game continues to change and evolve. Everyone focuses on salaries, which I totally understand. But there’s a lot of money being spent by clubs on baseball operations. There’s been an arms race in that regard, which nobody seems to understand,” said Henry. “It’s hugely important, because there’s so much data being injected into the game. It’s not just analytics. Everything is on the table — nutrition, sport science.

“But there’s still no substitute for a strong foundation of players. [Building the baseball operations infrastructure is] something we’re focused on. That doesn’t mean we don’t have the resources to sign the players that we want long term.”

The question of whether the Sox prove capable of doing that hovers over the winter. But in the middle of the summer, the focus remains on what the Red Sox can do with the players on their roster.

Do the Red Sox believe that this year’s team can compete for a title?


“No doubt … We’ve had a terrible spate of injuries this year to our starting pitching, but I think as we get those guys back we feel very good about where we are,” said Henry. “That said, there are some super-teams this year. It will be tough, but we know that in short series, the playoffs are quite different than the regular season. I think we’re set to be in the mix, and as we get people back, we’ll be tough.”

Alex Speier can be reached at Follow him @alexspeier.