Red Sox reported 'strategy' with Jordan Montgomery was a failure all along

Boston Red Sox fans have recently been slightly more optimistic about the team's chances to sign Jordan Montgomery, which, after this offseason, is not saying much.

The hope arrived with rumors of a trade involving Kenley Jansen. The closer is owed $16 million for the coming season, and if Boston could find a team to absorb his salary, that money would go a long way toward signing top-tier talent like Montgomery.

A few recent reports have stunted the slow-growing optimism. Jansen has not pitched since reporting to Red Sox spring training on Feb. 14 due to "general" lat soreness. There's been speculation about how the news affects the potential trade of the closer. The injury does not seem serious, however, other clubs may see it as an excuse to bargain further, despite the Red Sox organization admitting its reluctance to pay any of Jansen's 2024 salary of $16 million.

Even if Boston can trade Jansen, fans shouldn't bank on the deal being the savior of the 2024 team or the one move guaranteed to put Montgomery in a Red Sox uniform.

If forced to take a shorter deal, Jordan Montgomery may never consider coming to the Red Sox

Montgomery has been regarded as one of the top talents on the free agent market this winter, but it's seen relatively little action all offseason. Montgomery has been asking for a long-term deal with high average annual value after his World Series-winning 2023 campaign, and Red Sox fans are painfully aware of Boston's reluctance to spend in recent offseasons.

But since his market has been so slow and spring training has already started, the 31-year-old may have to modify his asking price or the number of years he's expecting out of a deal. The change may sound like it could be a good thing, but even Montgomery's increasing desperation may keep him out of Boston.

If the lefty is forced to accept a shorter deal, there's an "industry belief" that he'd like to play for a team with a chance to win, according to Alex Speier of The Boston Globe. The Red Sox's plan to sign Montgomery, if it can even be called a "plan," would never have worked in the first place.

The front office's budget plan is already coming back to bite them. CEO Sam Kennedy admitted to the Red Sox's hope to slash payroll and keep the team budget low as top prospects make their way to the majors. Other front office members have stated that even the most expensive team isn't guaranteed to win it all.

But spending money on the team would attract other talent. Had the Red Sox traded for Juan Soto or signed Yoshinobu Yamamoto, Cody Bellinger or even Jorge Soler or Teoscar Hernández, there may be less of a need to bargain with other players. A team's desire to win is clear based on who it covets and how much it's willing to pay to field a competent squad.

Needless to say, the Red Sox aren't winning any awards for the state of the roster. If anything, it's a deterrent to talent and potential new front office officials — Boston is being rejected left and right because of the way ownership treats the team like an afterthought among all of its other interests.

Even trading Jansen and an extra $16 million in the budget likely won't be able to get Montgomery to pitch in Boston unless the Sox offer him the long-term deal he's looking for. But if the Red Sox continue to lowball players to the point of disrespect, the front office can't have any hopes of the team improving. And it can't bank on taking advantage of cratering free agent markets.

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