With Their Eyes on the Future, the Red Sox Pick Their Man

A team of athletes marched into Fenway Park wearing Boston Red Sox uniforms on Monday morning. They played a game and won, beating a team owned by John Henry, who also owns the Red Sox.

Confused? It was just another day in the bewildering off-season of Major League Baseball’s most puzzling franchise, which swerved again this week from frustration to elation.

The game on Monday was the N.H.L.’s Winter Classic, and the Boston Bruins defeated the Henry-owned Pittsburgh Penguins, 2-1. Both teams wore baseball uniforms to the ballpark, and when Henry arrived, a fan on Van Ness Street, along the stadium’s first base line, spotted him in the parking lot and cried, “Pay Raffy!” Henry — whose ever-expanding sports portfolio had seemed to dampen his enthusiasm for spending on the Red Sox — may have listened.

Rafael Devers, Boston’s star third baseman, was said to be in the process of finalizing an 11-year, $331 million contract extension with the Red Sox on Wednesday. The agreement was first reported by the former major leaguer Carlos Baerga on Instagram. The deal would provide a jolt of optimism amid a dreary winter for a team coming off a dizzying decade: five playoff appearances, five seasons finishing at least 15 games out of first place in the American League East.

Devers, 26, is the last remaining position player from Boston’s 2018 championship roster. Shortstop Xander Bogaerts left for the San Diego Padres in free agency last month, and other homegrown starters, like Mookie Betts, the 2018 A.L. most valuable player, Andrew Benintendi, and Christian Vázquez, were shipped off in trades.

Boston Bruins players wore Red Sox uniforms at the N.H.L.’s Winter Classic at Fenway Park on Monday.Credit…Winslow Townson/Getty Images

In a phone interview on Wednesday morning, Chaim Bloom, the team’s chief baseball officer, explained why the time was right to make a long-term commitment to Devers — and why it wasn’t quite right to do so with the others.

“We absolutely want to keep him here and we want to build around him, and I know we’ve had players in recent history that we’ve felt that way about and it didn’t work out,” Bloom said.

“The difference now is when you’re making those bets, it’s not just about the talent of the player, it’s also about the positioning of the organization and are you well positioned to back up the bet? Are you well positioned to have the foundation around that core piece that will allow you to maximize the prime years of the player? And simply put, I just think we’re much better set up for that right now than we were a few years ago.”

It is impossible to know precisely how long-term deals with Betts and Bogaerts — or other free agents the Red Sox did not explore — could have altered the team’s long-term outlook. But Betts and Bogaerts are four years older than Devers, and Bloom believes the timeline matches up better with Devers, whose prime may coincide longer with Boston’s next glory era.

Then again, predicting the Red Sox’ fortunes has been vexing for years. After a last-place finish in 2012, they signed some midlevel free agents and won the 2013 World Series. After two more last-place seasons, they won three division titles in a row, culminating in the 2018 World Series title.

Chaim Bloom has been Boston’s chief baseball officer since 2020. Signing Devers to a massive contract extension is a departure from the way he has handled his roster thus far.Credit…Charles Krupa/Associated Press

A mediocre follow-up season led Henry to fire Dave Dombrowski, a probable Hall of Fame executive who specializes in building through acquiring superstars. The hiring of Bloom, who had been a top official with the thrifty and successful Tampa Bay Rays, a division rival, seemed to signal a shift in philosophy.

Bloom insisted that isn’t quite right. He believed the Red Sox needed to make hard decisions without tearing down completely — that is, try to contend without being reckless and weakening the future. His three seasons have reflected the range of outcomes for that kind of strategy: last place in 2020, a surprise visit to the American League Championship Series in 2021, and last place again in 2022.

“Rewind the clock three years, to when I got here,” Bloom said. “You had a club that obviously was coming off a lot of recent success, but clearly was not in a position where it was at or anywhere near the top of the division anymore. The talent wasn’t close in the farm system to replenish that roster, and there were quite a few commitments on the books. That’s not a great position to be in.

“And, really, the strategy all along has been to reset the table for a run of extended success, but to try to do it in a way where we were winning while we were doing it. There’s no question it’s a heavier lift to try to serve both masters. We were able to do it in 2021. Obviously in ’22, for a number of reasons, it didn’t work. But the way you do that is by maintaining elements of that core while replenishing the organization as much as you can with young talent. We have some of those young guys who are coming — some of them are going to play really prominent roles in ’23 — and there’s more coming behind that.

Boston came into this off-season with two big free agent decisions. Devers appears to be coming back while Xander Bogaerts, right, signed an 11-year, $280 million contract with the San Diego Padres.Credit…Winslow Townson/Getty Images

“If you continue taking on massive commitment after massive commitment, you never really get out of treading water around those.”

The Red Sox have largely avoided such deals lately. Officially, they have only three players signed beyond 2024: pitcher Garrett Whitlock, infielder Trevor Story and outfielder Masataka Yoshida, who signed last month for five years and $90 million after a decorated career in Japan.

Their other deals this winter have been risk-averse: two years each for infielder Justin Turner and the right-handed relievers Kenley Jansen and Chris Martin, and one year for the right-handed starter Corey Kluber and the lefty reliever Joely Rodríguez. The team hopes that three young pitchers — Whitlock, Tanner Houck and Bryan Bello — can establish themselves in the rotation, but the veteran starters — Kluber, Chris Sale, James Paxton, Nick Pivetta — offer little certainty.

The 2023 outlook would be different had the Red Sox made a stronger offer to Bogaerts before free agency or matched the Padres’ winning bid (11 years, $280 million). They could have moved aggressively on another choice from a deep class of free agents. Their passivity made you wonder if Henry simply didn’t want to pay the going rate for superstars anymore.

Would the Red Sox make those kinds of investments again? Bloom emphasized on Wednesday morning that they would.

“Absolutely — when it aligns with winning,” he said. “The end point is winning. It’s not commitments for their own sake. It’s commitments that you can win with. As we see, you win with these when they’re part of a complete team and complete organization. With every move, whether it’s a waiver claim or a large, multiyear contract, the endpoint is always: is this going to help us deliver to our fans what we’re here to deliver, which is winning baseball on an annual basis? And if the answer is yes, it’s something we should pursue.”

The Red Sox have passed on a lot of those options. They won’t be anyone’s favorite in the A.L. East. But a deal for Devers is a strong sign that a stubbornly pragmatic front office believes in its long-term direction.

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