Tuesday, July 30 is Major League Baseball’s trade deadline, and after barely dipping their toes in the buying and selling pools over the last two summers, Red Sox chief baseball officer Craig Breslow declared the club will be buyers this year. They’ve already made their first big spend, extending manager Alex Cora through the 2027 season. What does the roster need to get back to October? And who might they need to give up?

The Herald’s Red Sox beat writers, Gabrielle Starr and Mac Cerullo, discuss.

Gabrielle Starr: Somehow, the MLB trade deadline is already almost upon us. The Red Sox have indicated they plan to be buyers, so the coming days before the Tuesday, July 30 cutoff could get pretty chaotic. (Hopefully in a good way.) Let’s start with what each of us thinks would help this roster take their playoff hopes from dream to reality. I think a left-handed starter would be a significant help to the rotation, but it’s slim pickings out there. A potential reunion with James Paxton – designated for assignment by the Los Angeles Dodgers earlier this week – would probably be the most affordable active-player option, but he tired down the stretch with the Red Sox last year. (He did, however, just throw pretty well against the Sox on Sunday.) Breslow is also looking for a righty bat for this lefty-heavy lineup. There’s been a fair amount of Luis Rengifo chatter – and a switch-hitter would make the lineup interesting, especially given how Boston has struggled against southpaws this year – but I’m wary of adding a middle infielder to an organization that already has so many talented infielders at the Major- and upper minor-league levels. (Rengifo isn’t a free agent until 2026.) What do you think they need?

Mac Cerullo: A starting pitcher is a must. I don’t know if a left-hander is essential but it would give the Red Sox a different look considering they don’t have any viable lefty starters. I’m fine with a Paxton reunion, he’s been pretty inconsistent in Los Angeles this season but he’s made every start, which is the most important thing for a guy who’s missed as much time as he has these past few years. If not Paxton, I’d like to see the Red Sox try to land Jack Flaherty from Detroit. He’s bounced back from last year’s disappointing second half and posted excellent numbers with 100.1 innings, 127 strikeouts, and if he qualified his 0.964 walks and hits per innings pitched would rank third in the American League. He’d actually raise Boston’s ceiling, while someone like Paxton would patch up the floor and protect the club from crashing through. I do like the idea of Rengifo, too. He’d give the club another right-handed bat and a more established second-base option in the short-term, and over the long-term he could be a really good super-utility type. Think more of an upgrade over Romy Gonzalez and Jamie Westbrook and less of an impediment to Vaughn Grissom or Marcelo Mayer.

GS: The Red Sox can certainly afford – both financially, and in terms of prospects – to bring in someone like Flaherty or even Tarik Skubal or Garrett Crochet, but asking prices will be sky-high, given how many teams need pitching, and it’s unclear how aggressive the Red Sox are willing to be. After all, they promised “full throttle” last November, and the offseason was decidedly not. I’d like to see them actually go “full throttle” now, and add a pitcher who could help in short- and long-term. Many evaluators’ preseason predictions had this being something of a bridge year for Boston, but this team has proven they’re further along than that. The future is now. They shouldn’t be waiting for Mayer, Roman Anthony, or Kyle Teel to keep building. Speaking of Boston’s new “Big Three,” do you think there’s a world in which the Red Sox are willing to part with any of them? I’ve seen some pretty crazy trade proposals, but I’m told the organization still sees the trio as untouchable.

MC: I can’t see any of them being dealt. If the Red Sox were willing to give them up then yes, that would potentially put guys like Crochet and Skubal on the table, but executing a deal like that would be so wildly out of character that it just doesn’t seem realistic. Plus, is this year’s Red Sox team one player away from winning a championship? Probably not, so a home-run swing like that may not be the best play. The Red Sox do have tons of other prospects though, and at some point they’re going to have to make some decisions on who to keep and who to move. Is there anyone in particular you think would make good trade chips if the club does swing a deal or two?

GS: I don’t think the trio is even on the table, so let’s set that aside. One addition might not be a World Series difference-maker, but two could be; Nathan Eovaldi and Steve Pearce certainly were in 2018. Besides, with someone like Crochet or Skubal, neither of whom is a free agent until ‘27, even if one of them didn’t get the Red Sox to a championship this year, he could be a key part of one in the coming seasons. I’ll also add that while I know Alex Cora has spoken about getting greedy, and I’ve been told he’s been talking World Series since early in the offseason, the Red Sox making the postseason at all would be a significant improvement after two last-place finishes (three in four years), and a pretty epic defiance of the very low expectations. As for trade chips, they have so many top prospects in Double- and Triple-A who will be Rule 5 Draft-eligible this offseason; instead of waiting for teams to steal them in the draft for the meager sum of $100,000, the Sox should use players they don’t plan on protecting, to reel in a great big-league fish. I touched on this in my ‘7 Questions’ column last week, but I think the trade deadline actually comes at a perfect time for the organization: the roster could use reinforcements, the payroll is low, and top prospects who look ready for promotions – Teel, for example – but the upper levels of the farm system are a bit overcrowded. In particular, there are quite a few talented infielders who are close to big-league readiness, and little room for them in Boston. I could see second baseman Nick Yorke being moved; he’s been tearing the cover off the ball since his promotion to Triple-A, hitting .318 with a .921 OPS and 41 hits over 33 WooSox games. Plus, he’s walking almost as much as he strikes out. There’s also Nick Sogard, Niko Kavadas, Eddinson Paulino and Blaze Jordan. The Sox outfield is pretty crowded with young talent too, so Allan Castro could be another trade candidate. All are Rule 5-eligible this year.

MC: Yorke and Jordan are the ones from that group I feel would be the best trade chips in terms of how valuable they are and how difficult their paths to the majors would be in Boston. We probably shouldn’t discount the possibility the Red Sox could unload some pitching prospects, too. After the draft, Red Sox director of amateur scouting Devin Pearson made an interesting comment that didn’t get much attention after he was asked what kind of impact the club adding 14 new arms would make. He said: “It’s important, not only for the system in terms of having some pitchers we’re excited about but also from the acquisition side, just having some flexibility on trades and things like that.” To me, that sounds like he’s suggesting the influx of new arms could make some of the club’s more established pitching prospects expendable, which maybe means guys like Wikelman Gonzalez or Richard Fitts could be packaged in a deal as well.

GS: That’s a great point, though kind of funny given how long they’ve been scrounging and scrimping just to build up some semblance of pitching depth. But as we’ve been going back and forth here, the Red Sox and Cora agreed to an extension out of the blue, so I feel like we need to switch to that before we wrap this up, because it’s quite a pivot for Cora. He’d been adamant about not talking contracts during the season, and now they’ve not only had those talks, but got a deal done to keep him in Boston through 2027. This is the strongest indicator that the Red Sox are ready to be The Red Sox again, and Cora essentially confirmed as much when the deal became official on Wednesday evening. I don’t think Cora would’ve been willing to finalize an extension if the Red Sox weren’t planning on buying at the trade deadline and in the upcoming offseason. He knew he’d have several suitors if he became a free agent this year, so if he felt that the Red Sox weren’t doing everything possible to win, all he had to do was ride it out. The extension also speaks volumes about Cora’s and Breslow’s relationship. Breslow could’ve waited out the year and chosen someone else, but he flew to Colorado this week to get this done with Cora as quickly as possible. I’ll be honest, I’ve really missed this aggressive Red Sox energy. What do you think?

MC: It’s huge. The last five years have been such a bummer, and throughout that stretch it’s just felt like the Red Sox were spinning their wheels. Now with Cora’s future with the club settled, it actually feels like anything might be possible. When was the last time we could really say that? I don’t know if the Red Sox are going to go out and blow people away at the trade deadline — my guess is they’ll take a more responsible approach rather than go all-in — but with the resources it has at its disposal, the club could theoretically go out and get anyone it wants. But more importantly, it feels like the Red Sox are ready to get serious and actually compete. Even if this season proves to be a stepping stone towards an eventual championship run down the road, this is probably the most exciting time to be a Red Sox fan since the 2021 playoffs.

GS: Absolutely. Rafael Devers’ extension in January ‘23 evoked more relief than excitement; I don’t think anyone viewed last year’s squad as serious contenders, plus keeping Devers was kind of the bare minimum after giving up Mookie Betts and Xander Bogaerts. A very expensive bare minimum, but a bare minimum nonetheless. Meanwhile, a lot of projections described this as a bridge year, at best, but I was more optimistic. And with Cora staying, even more so. Before Opening Day 2021, I predicted – on camera – that the Red Sox would be better than people expected, fun to watch, and might even “sniff” a Wild Card. Not the first time my preseason gut instincts were proven right, either. Bring on the trade deadline.