DALLAS – As the Boston Red Sox weigh various ways to improve their roster, there is one certainty: Pitching is a priority.

But the reality of acquiring a front-end starter became more difficult on Tuesday.

Top free agent starter Max Fried signed an eight-year, $218 million contract with the New York Yankees this afternoon. According to him, the Red Sox were finalists because of his merits The athletic oneis Ken Rosenthal.

A few hours later, right-hander Nathan Eovaldi, a center fielder with whom the Red Sox had been linked, signed a three-year, $75 million contract to remain with the Texas Rangers.

The pitching market was off the charts this winter when Blake Snell signed with the Los Angeles Dodgers on a five-year, $182 million deal just before Thanksgiving. If they want to improve, the Red Sox must meet current market demands.

“To attract free-agent talent, you have to be willing to be uncomfortable,” Chief Baseball Officer Craig Breslow said on the second day of the Winter Meetings at the Hilton Anatole in Dallas. “This can’t be about doing what feels perfectly comfortable.”

However, principal owner John Henry remains hesitant to offer longer contracts to pitchers over 30. The exact contract length limit is unknown, but Fried’s eight-year deal is likely to fall into that category. Breslow was asked Monday if the club was against five-year contracts with pitchers. He said such an approach to decisions would close opportunities.

“There is a very, very fine line between being aggressive, prioritizing competitiveness in 2025 and being irresponsible and reckless,” he said. “But I think we have to compete on that frontier to attract players.”

Several people within the Red Sox brought up Fried’s name in the offseason because he was a good fit for the club, indicating he had long been their priority in the pitching market. Now they have to change course. Again.

The Red Sox missed out on Max Fried. Now it’s time for Plan B. (Brett Davis / Imagn Images)

While the Red Sox have said they want to spend $60 million under the luxury tax line and are currently there, the options for free-agent starters are shrinking with Corbin Burnes the only remaining upper arm. Given the evolution of the pitching market, Burnes will not be taking any discounts.

Breslow wouldn’t say whether the market has given him a reason to focus more on acquiring a pitcher via trade.

“There are different ways to be reckless and irresponsible,” he said. “If you’re a team that runs controllable starting pitching in the front-of-the-rotation, you know very well what the market looks like in free agency and you can legitimately demand a pretty significant return.”

On the trade market, Rosenthal reported earlier Tuesday that while the Red Sox remained interested in Garrett Crochet from the White Sox, the Yankees and Mets were Crochet’s “most aggressive suitors.” However, with the signing of Fried, the Red Sox’s calculations could change. Rosenthal noted that no deal for Crochet was considered closed. The athletic one‘s Jim Bowden recently suggested that a Red Sox deal for Crochet would need to include at least Triston Casas and Wilyer Abreu, as well as other mid-range prospects.

Casas is considered a trade partner this winter, along with Abreu and, to a lesser extent, Jarren Duran, with club officials recently indicating they are more inclined to build on Duran than trade him.

The Red Sox have reportedly already offered Casas a deal with Seattle but was rejected. Ryan Divish of the Seattle Times reported Monday that the Red Sox offered Casas for starters Bryce Miller or Bryan Woo earlier this offseason, but the Mariners declined. Divish hinted that the Mariners might be more interested in a deal between Casas and Luis Castillo. The 32-year-old right-hander has three years remaining on a five-year, $108 million contract with an average annual value of $21.6 million. Last season, Castillo posted a 3.64 ERA with a 24.3 percent strikeout rate in 30 starts.

Another trade option emerged on Tuesday when the San Diego Padres floated the idea of ​​trading starter Dylan Cease, a pitcher the Red Sox have been linked to in the past.

Meanwhile, Japanese free agent Roki Sasaki was officially assigned to the MLB on Tuesday, presenting a unique case as a pitcher who can only be signed to a minor league deal as an amateur free agent due to his age. According to his agent Joel Wolfe, the 23-year-old is scheduled to meet with teams next week, but he won’t be able to sign until Jan. 15, when MLB’s new international signing period begins. International bonus money is capped for each team and ranges from $5.1 million to $7.5 million. The Red Sox currently have about $6.2 million, but Wolfe said Tuesday he advised Sasaki not to sign for the money because the difference is negligible and he should focus on comfort and long-term fit.

Wolfe noted that Sasaki had a difficult time with Japanese media criticizing him leaving Nippon Professional Baseball for MLB at a young age, which is viewed as disrespectful in Japan. Wolfe noted that Sasaki might benefit from a smaller market team with less media focus and has paid attention to how the teams have performed in recent years. These points may be detrimental to the Red Sox case, but they haven’t stopped them from making a strong case for him.

A Red Sox posse, including Breslow, traveled to Japan last summer to see Sasaki in person, although Wolfe said more than a dozen teams had scouted Sasaki in Japan. Today, much of the scouting of Japanese players is done via video, and while MLB scouts are prohibited from speaking to NPB players, in-person scouting is viewed as a sign of respect in Japanese culture. These trips also allow teams to see how players interact with teammates and fans. Executives also often meet with people close to the players to gather information since they cannot speak to the players directly.

Sasaki’s posting window expires on January 24th, but the Red Sox can’t wait to bolster their rotation before then. Whatever direction the Red Sox take with pitching, their options are dwindling.

As Breslow gauged his confidence in adding a pitcher, he offered some insight into what has seemingly been a frustrating week so far.

“If you were to track my confidence over the last 48 hours or so, there would be ups and downs in this process,” he said. “I just learned that we have to stay committed. We have to have conversations. And if we feel that there is a chance to achieve something, we have to be brave and try to push it over the limit.”

(Top photo by Craig Breslow: Kim Klement Neitzel / Imagn Images)