Top remaining free agent pitcher fits Craig Breslow’s words, but not Red Sox’s actions

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FORT MYERS, Fla. – “I think what what we have in front of us is an opportunity to to continue to look for ways to improve the long- and short-term outlook of the team.”

Unfortunately, that wasn’t Craig Breslow talking about the Red Sox signing Jordan Montgomery.

Most of what Breslow said in his first spring training media availability as the club’s rookie chief baseball officer would be true of Montgomery, but wasn’t about the starting pitcher, who remains a free agent and obvious solution to Boston’s problems.

“Things haven’t come together in a way that I had anticipated,” Breslow admitted, “but nonetheless, it’s not going to stop us from trying to pursue that vision of building this standard of quality and consistency that I’ve spoken about.”

Montgomery has proved to be a high-quality and consistent pitcher. He owns a 3.48 ERA over the last three seasons, during which he made 94 regular-season starts between the Yankees, Cardinals, and Rangers.

“I think I’ve been very outspoken about trying to address not just kind of, pitching at the Major League level and our starting rotation, but also building out a pitching development pipeline,” Breslow explained. “I think we’ve made some progress in terms of some of the staff and infrastructure build-out.”

Signing Montgomery would certainly address pitching at the Major League level and the starting rotation. He ranked in the 93rd MLB percentile in Pitching Run Value and 82nd in walk rate (6.2%). He’s an above-average pitcher in many ways, including average exit velocity, and home-run, chase, and hard-hit rates. Opposing batters have hit .244 with a .680 OPS against him over the last three years.

Trying to improve a big-league team that’s projected to finish at the bottom of its division once again – which would make four times in five years and thrice consecutively – whilst also overhauling player development, specifically pitching development, for a brighter future is a balancing act. And an incredibly difficult one in a sports mecca such as Boston. Said infrastructure build-out could end up having one of the biggest impacts of any offseason move made by a club this year, but it won’t be immediate. In the meantime, the Red Sox need proven pitching to complement the young core they keep talking about.

“We’re also aiming to be as competitive as we possibly can,” Breslow said on Tuesday. “I think this is going to be a very competitive team, I think it’s going to be a team that is going to take, that’s going to see its players take a meaningful step forward.”

Montgomery would almost certainly make the Red Sox a more competitive team and help them take a step forward. He’s a reigning World Series champion who owns a 2.63 career postseason ERA over eight games between Octobers ’20, ’22, and ’23.

This offseason, Red Sox made more headlines for what they haven’t done than anything they’ve done. Their top executive is willing to cop to that, to an extent.

“It takes a lot for these things to come together,” Breslow said of adding big-league pitching via free agency or trade. “Outside of a handful of situations, they haven’t, but you know, it’s not because we haven’t recognized and tried to pursue every possible path.”

But one very possible, very obvious path – which many industry experts can’t believe the Red Sox haven’t jumped on – is Montgomery. He even lives in Boston now, as his wife is doing her residency at an area hospital. He is literally there for the taking.

“It doesn’t make a ton of sense to speak about specific players,” Breslow said when asked about Montgomery and Blake Snell, the top two remaining free-agent starters. “We’re going to remain engaged (with the market). There are some really talented players still available.”

“I think there is going to be a time where we behave as the Red Sox have,” Breslow said. “And we need to make sure that when we do that, we do it in a very disciplined way.”

Except, the Red Sox didn’t used to be disciplined. There was nothing disciplined about Manny Ramirez’s contract, a franchise record at the time. Nor David Price’s, which broke Ramirez’s record and the record for any MLB starting pitcher.

“You wanted him. You got him,” Bob Ryan wrote in the Boston Globe after the Red Sox and Ramirez made an eight-year, $160 million pact in December 2000. “Ask and ye shall receive… Did the Red Sox really want to do this? Who knows? The truth is that they were harassed and bullied into it by you, the long-suffering and angry Red Sox fan… Raking in the money without turning around and using it on a major baseball household name just wasn’t going to fly… the Red Sox had to do something.”

Three last-place finishes in four years is not an 86-year drought (and curse), and Montgomery isn’t a household name. He’s no Shohei Ohtani or Juan Soto. But it’s no longer acceptable to lose and keep losing in Boston, and Montgomery is available, reliable, familiar with the division, and definitely affordable for a team nearing the $5 billion valuation threshold.

And almost everything the Red Sox say will continue reminding anyone listening that there’s a clear solution staring them right in the face, and they’re not seizing it.

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