For much of the season, whenever I was asked about what the Red Sox would do at the trade deadline, my answer was simple and unwavering: Sell. Then sell some more.

My answer was based on 1) common sense and 2) discussions with people around the game.

The rationale was clear: in his first year as the chief baseball officer, Craig Breslow would assess the situation dispassionately. He could see that this was a flawed Red Sox team with little in the way of expectations. Certainly, ownership, through both words and deeds, had communicated that they weren’t demanding an end to the franchise’s postseason drought.

Breslow could rightfully decide that the Sox had little chance to sneak into the playoffs. And even if they did, to what end? There was no evidence to suggest that the Sox could somehow become this year’s version of the 2023 Arizona Diamondbacks.

It would be far better for Breslow to sell off the team’s assets – free agents-to-be Kenley Jansen, Chris Martin, Nick Pivetta and Tyler O’Neill – in exchange for additional prospect inventory. This would be an opportunity to stockpile some young players for the future, and be in that much better position when the Red Sox are actually positioned to compete for a championship.

If he needed further convincing, Breslow could note what happened to his predecessor, Chaim Bloom.


Bloom received mixed signals from ownership at the last two deadlines – along with instructions in 2023 to not add to the payroll – and ended up trying to walk the tightrope between providing some help for a playoff push while also auctioning pieces that weren’t part of the organization’s future plan.

That strategy backfired, sending a mixed message to the players while also inspiring Manager Alex Cora and some coaches to wear “Underdog” T-shirts in a mocking retort to Bloom’s remark that the Sox were underdogs to qualify for the postseason. Nobody won.

And given the need to make a choice and stick with it, it was easy as recently as a week ago to pick “sell” mode for Breslow. With no evidence that the fan base or his bosses believed in the team’s October chances, why not do all that he can to improve the club’s future? Peel off some expiring contracts and live to fight another day.

Now, I’m not so sure.

Now, after the events of the last 10 days, I don’t know anymore.

Because for that admittedly brief period of time, the Red Sox have looked very much like a team with designs on getting to the playoffs. They’ve developed an offensive identity, one partly (and unexpectedly) based on speed and athleticism. In six of their last eight games before Friday, the Red Sox scored seven or more runs by putting pressure on the opposition.


Who thought the 2024 Red Sox might do a reasonable impression of the 1985 St. Louis Cardinals?

It’s important to note, too, the quality of the competition in this latest stretch. Four of their last seven wins were against the Phillies and Yankees, arguably the two best teams in the game.

Further, the Red Sox are about to benefit from the return of two key contributors: outfielder Wilyer Abreu and Triston Casas. Already a top-10 team in most offensive categories – including runs scored, OPS, OBP and homers – Boston soon should be even better.

Such decisions with long-term consequences aren’t made on the basis of a week and a half. It’s not out of the realm of possibility that the Red Sox could soon encounter a losing streak that could wipe out the gains that have been made in the last little while. More evidence to cement the idea that the Red Sox are worth investing in is still needed.

But if the Red Sox keep playing with this newfound confidence, if they continue to ride the momentum earned from their hot streak, how can Breslow deny them help at the end of July? How can he tell the players, face to face, that he didn’t believe they were worth an additional investment?

As a former player, Breslow clearly understands the culture of the clubhouse. He knows, first-hand, how uplifting the arrival of some help at the deadline can be. When players show they’re worthy of belief, they expect that the powers that be will respond in kind and provide assistance for the stretch run.


Understand: this doesn’t mean that Breslow might now be tempted to swap Marcelo Mayer or Roman Anthony or Kyle Teel for a big rental. No matter where the Red Sox find themselves in the standings in late July, Breslow isn’t about to do anything to jeopardize the team’s chances of competing in the near future.

He may not even be interested in trading for any rental players at all, and instead might focus his search on acquiring players who could contribute beyond next year. Or, he might make small, complementary-type moves to land some more bullpen depth or a righty bat for the bench.

It’s a given that the Red Sox will have to stay at least this close to the wild-card chase to warrant an upgrade. Should they nosedive and fight to stay at the .500 mark, the point will be moot and Breslow will correctly revert to his default setting of looking ahead and putting his free agents up for auction.

On the other hand, if the last two weeks are indicative of a newfound ability for the Red Sox to compete and insert themselves more fully into the postseason picture, Breslow will have to re-examine his approach for the deadline.

Both the math and his own team’s clubhouse will make that necessary.

AS AN EXAMPLE of how quickly things can change, last week, we had a talent evaluator rank Boston’s potential trade pieces in terms of the value they could bring in return.


Now that the Sox might shift to “buy” mode, what sort of holes might they address?

1) Right-handed bat

The Red Sox remain very left-handed. When Abreu and Casas return, the best lineup might only feature three or four righty bats: catcher Connor Wong and Tyler O’Neill, center fielder Ceddanne Rafaela and shortstop David Hamilton. Everywhere else, the Red Sox would have a lefty.

The return of Abreu frees up some outfielders to serve as the right-handed part of a DH platoon shared with lefty Masataka Yoshida. Both Rob Refsnyder and O’Neill can serve in that capacity, with an outfield of Jarren Duran (left), Rafaela (center) and Abreu (right).

But they could use a more traditional thumper in that role. One interesting name: Tommy Pham, who won’t be of much use to the White Sox down the stretch, but would appeal to a number of contenders. As an added bonus, Pham would bring some intensity and leadership to a mostly young collecting of players.

2) High-leverage reliever


It remains to be seen just what Chris Martin can provide in the second half. He’s been limited by a left-shoulder injury that has occasionally thrown his mechanics into a mess. And, of course, he recently spent time on the IL because of anxiety. He’s also 38.

The Red Sox might have use for a more traditional power set-up man to team with Martin in the seventh or eighth inning. Martin’s strikeout rate is still above the league average, but acquiring someone else with swing-and-miss stuff might be a good idea.

3) Starting pitching depth

Since the start of the year, Red Sox starters have over-performed. Tanner Houck has emerged as the staff leader, and Kutter Crawford, despite a rocky stretch, has further solidified his standing. Brayan Bello can be frustrating with inconsistency, but the talent is clearly there. Pivetta is solid and perhaps capable of a big second half. No. 5 starter Cooper Criswell has been a pleasant surprise.

After that group, the Red Sox are thin. At Worcester, the depth amounts to Josh Winckowski and Richard Fitts. That means the Red Sox will be on the lookout for a back-end arm.

Of course, so will about a dozen or more other teams, driving the price up considerably.

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