Boston-wearing athletes led a team to Fenway Park. Red Sox They wore uniforms Monday morning. They won against John Henry’s team, and also owned the uniforms. 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 This Wednesday. Carlos Baerga (ex-major leaguer) first reported this agreement. on Instagram. This deal could bring some optimism to a winter that has been difficult for the team after a decade of dizzying achievements: Five playoff appearances and five seasons in which they finished at least 15 points behind first place in American League East.

Devers, 26, is the last remaining position player from Boston’s 2018 championship roster. Shortstop Xanderbogaerts went to San Diego Padres as free agent last month. Mookie Betts is the 2018 A.L. most valuable player, Andrew Benintendi, and Christian Vázquez, were shipped off in trades.

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.

“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. Betts and Bogaerts have a four-year difference. DeversBloom agrees that the timeline is more compatible with. Devers, whose prime may coincide longer with Boston’s next glory era.

One more thing: Predicting the Red Sox’ fortunes has been vexing for years. Following a 2012 last-place finish, the team signed free midlevel agents who won them the 2013 World Series. They won the 2018 World Series title after winning three consecutive division titles.

Henry was disappointed with the results of his second season and fired Dave Dombrowski (a Hall of Fame candidate who is known for building by acquiring stars). Bloom had previously been an official at the Tampa Bay Rays (a division rival) and was now a key member of their team.

Bloom insisted that isn’t quite right. He was convinced that Red Sox needed to make hard decisions without tearing down completely — that is, try to contend without being reckless and weakening the future. The range of results for this strategy has been evident in his three seasons: last in 2020 and a surprise trip to the American League Championship Series 2021. He was also last in 2022.

“Rewind the clock three years, to when I got here,” Bloom. “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.

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

It Red Sox They have avoided these deals in recent years. They have three signed players beyond 2024, namely pitcher Garrett Whitlock and Trevor Story. Outfielder Masataka Yashida signed last month, and will be paid $90 million over five years.

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.

If the 2023 outlook had been different, Red Sox made a stronger offer to Bogaerts before free agency or matched the Padres’ winning bid (11 years, $280 million). They could have acted aggressively to get another free agent from their deep group. Their passivity made you wonder if Henry simply didn’t want to pay the going rate for superstars anymore.

What about the Red Sox These types of investments are worth making again. Bloom stressed Wednesday morning that they would.

“Absolutely — when it aligns with winning,” He stated. “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.”

It Red Sox Many of these options have been passed up. They won’t be anyone’s favorite in the A.L. East. But a deal for Devers It is a clear sign that an inflexible front office still believes in its long-term goals.