In signing Lucas Giolito and (surprisingly) trading Chris Sale, the Red Sox haven’t done a lot to upgrade a rotation that struggled in 2023. Within the last week, chief baseball officer Craig Breslow stated that it has “been a challenge” in finding additional pitching, while club president Sam Kennedy seemed to downplay the idea of a big free agent splash by saying that the team’s payroll “probably will be lower than it was in 2023.”

Breslow did state that the Sox were continuing to look at free agent and trade possibilities, and it appears as though the club hasn’t given up on the idea of still landing a bigger name. According to Pete Abraham of the Boston Globe (X links), the Red Sox are “still in contact with the top remaining free-agent starters.” Reporter Marino Pepen is more specific, writing (Spanish language link) that the club has been continually talking with left-hander Jordan Montgomery.

There is no sense that a deal with Montgomery or anyone is particularly close, or necessarily even a realistic option. Abraham wondered whether any pursuits of frontline pitching were “serious or not,” or if the team’s explorations could be “just posing so they can claim they tried” in the wake of growing angst in Red Sox Nation.

MLBTR’s list of the offseason’s top 50 free agents still has 19 unsigned names. Blake Snell (ranked 4th), Montgomery (6th), Mike Clevinger (30th), and Michael Lorenzen (34th) are the only clear-cut starting pitchers of that 19-player field, with Jakob Junis (47th) perhaps more of a swingman candidate though he has a lot of starting experience in the past. It is fair to cite Snell and Montgomery as the true front-of-the-rotation types remaining, as landing Clevinger, Lorenzen, or Junis might help Boston’s staff, but perhaps not move the needle much in terms of quieting fan discord.

Breslow is naturally only under an obligation to make the team better, not to acquire only marquee talent. However, the CBO is already facing a lot of heat in his first few months on the job given how the Red Sox are coming off a pair of last-place finishes in the AL East, and because team chairman Tom Werner raised expectations with his now-infamous “full throttle” comments about Boston’s winter plans.

Terms like “in contact with,” or “checking in on,” or “showing interest in” are commonplace during hot stove season, and this lingo can represent anything from due diligence texts to an agent or a more serious push to close a deal. It is common for executives to keep in touch with agents about any number of available players, usually in the form of some contact early in the offseason to establish particular interest in a target or two, and then the two sides can circle back multiple times over the coming weeks or months as markets develop.

To this end, it isn’t surprising that the Sox are still testing the waters on the top pitchers, since there’s no downside in such explorations while the players are still unsigned. As Abraham notes, the Red Sox “could be hoping prices drop and somebody like Montgomery makes sense” within what might be a somewhat limited 2024 budget, yet if this situation ends up being the case for Montgomery or Snell, it is far from automatic that Boston would necessarily be the first choice for a pitcher willing to accept a reduced deal.

Montgomery has been linked to the Red Sox for over two months now, with some suggestion that Montgomery is the team’s preference over Snell. Unlike Snell, Montgomery doesn’t come attached to qualifying offer compensation, and Montgomery has a steadier and more durable track record even if Snell’s peaks (i.e. two Cy Young Award-winning seasons) are higher.

Montgomery and his wife McKenzie also have a personal connection to Boston, as McKenzie is currently on a dermatology residency at a local hospital. These family ties have led to speculation that Montgomery might therefore be more open to favoring Boston as a landing spot, though that obviously doesn’t mean Montgomery would leave tens of millions on the table to give the Red Sox any kind of discount. MLBTR’s Nick Deeds explored Montgomery’s market in a reader poll earlier today, and given the number of known suitors — the Rangers, Giants, Yankees, and Angels — and possible mystery teams still on the periphery, there isn’t any indication that Montgomery and his representatives are yet willing to lower their demands.

Only the Red Sox (and the players’ agents) know how realistic Boston’s chances might be of actually landing a notable free agent, so a trade might be the more realistic route towards adding pitching help. Trades have been Breslow’s preferred method of transaction thus far in his brief tenure as chief baseball officer, as the Sox have already brought in Tyler O’Neill and Vaughn Grissom in swaps while dealing away Sale, Alex Verdugo, and Luis Urias. Giolito’s two-year contract and Cooper Criswell’s one-year, $1MM pact are thus far the only Major League signings of the Breslow era.