Will the Red Sox add a front line starter for 2025?

I think its pretty clear based on the projected FA market and the names that popped up at the deadline, Corbin Burnes should be the #1 target. Would love to have Skubal but unless he can be had without dealing any of the big 3 I just don't see it happening. Fried could be an option as well but wouldnt quite put him on the same tier as Burnes and Burnes now has a season (or nearly a season) in the AL east under his belt and has been as good as ever. Outside of Burnes, I'd be heavily in on Roki Sasaki. The trade market I would look at for bullpen help as there is no clear closer for next season. Kenley and Martin are FA's, Liam Hendriks will be entering his age 36 season and Whitlock (assuming they do the smart thing and return him to the pen for good) will be coming off another major injury. I'd also keep an eye on the righty bats available on the trade market as well. Vlad jr stands out. Robert to a lesser extent.

Criswell, according to his player page here will be out of options next year. It shows options used in 21, 23 and he's already been optioned this year, just guessing his player page not updated and cannot see him worthy of a 26 man spot over an entire season, he's a swingman/break glass emergency starter type.

Wild longshot/hope anything left for dirt cheap: Patrick Corbin.. If he'd be willing to sign for dirt, dirt cheap and see if Bailey could fix anything with him that's been wrong with him like seemingly for years now.

He was quite happy to get out of Philly and to Boston originally, but like u wrote.. Getting flip flopped like he has can change one's mind and available SP this winter is pretty lean. Would see him myself as getting comp salary (per season) to Flaherty, as Nick has consitency (innings wise) to his credit if nothing else.

Look back now and remember Boston gone out and given Eovaldi the kind of money you suggested early on in the offseason 3 short years ago and how much better off the team would be and Eovaldi is head and shoulders above Pivetta.

Think myself whatever SP they bring in this offseason will be either via trade, or a reclamation project, like a Corbin type.

As of right now I'd say there's only 3 guys who should be slotted into the rotation for next season: Bello, Houck and Giolito. Thats most likely your 2-4 spots of the starting 5. Priester could be an option for the 5 spot if they can get him straightened out. The #1 spot should come via free agency or trade. (Burnes would be my #1 option). Pivetta can be let go. Craword either long man or trade chip. Criswell would likely depend on crawford. If he's dealt then criswell can take his spot as long man. Whitlock should be locked into the pen without question. There is 0 reason to try him as a starter again and realistically the pen is going to need him next year. 

On Whitlock it actually worked out well this year before he got injured as a starter. I personally would prefer him as a "stopper" so to speak, with Slaten as the set-up and Hendriks as the closer, but I wouldn't be surprised if the team considered trying to use him again as a starter.

This question reminds me of when I was discussing the question of “Should the Celtics trade Jaylen Brown?” A few years back with a grad school classmate of mine.

We discussed that, in more economic terms, the market for that type of deal was incredibly small (and thus more unlikely), because (1.) the pool of players of a caliber where you’d consider trading a star (JB) is already very limited, and (2.) the respective teams those stars belong to carry massive deal-making implications. (division rival? No-go. A team in a contention window? A no-go. A player that would not fit the club culture or city of Boston? No go.) Once you use these filters on an already small list, we were left with about 3 names of players that would even make sense discussing. Nothing else was realistic.

The ongoing search for top-flight starting pitching seems to have a lot of parallels, albeit on a slightly larger scale. The market is still so incredibly small, and within that small market, teams may or may not have motivation to deal with the Red Sox for a variety of reasons.

So I have taken this approach to thinking about the SP search:

Which teams have the personnel to fit the need (high end SP), are in a place to let go of said arms, and would be open to dealing with the Sox?

Clubs I generally rule OUT:

-All ALE competitors. I don’t want to give them top positional talent in exchange for the health risk that pitchers carry.
-CLE, KC, MN, HOU - AL WC competition without high-end SP to spare
-PHI, SD, MIL, CHC, NYM, STL, AZ - NL clubs I perceive as ‘going for it’ without SP to spare

So who is left? Of the remainder the clubs I keep coming back to include:

Seattle: Yes, a major WC competitor. But a team with 5 excellent starters, and clear need for positional talent to pair with J-Rod. Any of their top 5 would be great options, albeit at differing price points. If taking on Castillo’s $75M/3 contract, maybe they can get away with a package of 2nd tier prospects.

Cincy: Lodolo, Abbott would both fit nicely as controllable LHSP. Burns/Rowder coming soon to join Greene. Lodolo likely more realistic due to contract term. Their OF is bad at present and does not project well anytime soon, so there is potentially a strong match between orgs here.

Pittsburgh: As we saw with Yorke/Priester, the respective needs and areas of excess match up well with both of these clubs. 3 of their top 5 prospects (ahead of Yorke) are RHP in AAA. With them ready to join Skenes next season, Mitch Keller and Jared Jones could theoretically be available for the right match of positional talent. Is there another match to be made here?

Detroit: If they feel they can’t work out an extension with Skubal, he will eventually be moved. They are playing with fire, because his value could go to 0 on one pitch, and they are not going to contend within the scope of his contract (which has 2 more ARB years of control). It would require a godfather offer if he is healthy and performing at recent levels, but the Sox have the capacity to do so if they so choose.

White Sox: Crochet an obvious fit if White Sox FO becomes more realistic with asking price.

Oakland: Mason Miller (not a starter), another strong org match for working out a deal. This would be high on my list for the pre ‘26 offseason, when Big 4 have already integrated into MLB roster and are no longer the key targets of other clubs.

Washington: Mackenzie Gore is the only arm of interest I am aware of in Washington, but he is not quite the front-end talent they desperately need. Maybe as a 2nd add, at a lower prospect cost.

Miami: Sandy Alcantara. Yes, please. I fully expect irresponsibly high asks, in which case, move on. But if a deal is to be made, I prioritize here.

If they acquire 1 via trade and 1 via FA, they will be set up exceptionally well. They have the means to do both, and have warchests still in-tact.

If I could have my semi-realistic pick (i.e. no Sasaki), I would go:

-1 of Seattle’s back 3 (Castillo, Woo, Miller) without totally breaking the bank. Wilyer would be a great fit in Seattle.
-Max Fried via FA unless market gets completely insane, in which case pivot to a 2nd trade acquisition, hopefully with Pittsburgh or Cincy.
-And then go get Mason Miller before another WS contender does.

Can name 1 Dombrowski might be tired of and looking to unload, only would require Philly paying 50% (or more) of remaining 36m left owed in 25-6.. Taijaun Walker, who have always liked myself as a gritty competitor that analytics oriented people can't stand.

His velocity is down a 1.5mph this year, some is his various injuries more than likely which have been several. Walker won't fold during an inning when it gets tough and is a throwback style mentality attitude.

Have wanted Boston to get him since early M's days. Forget the no flashy spin rates. He's not going to fold was how always judged him and if could get Philly to subsidize the salary and not want a large return? I'd like him.

I am not going to say it so absolutely as you are but I do kind of have that type of feeling as well that they will come away with Burnes this offseason. Their position player core is pretty much set for the next 2-3 seasons at least if not more with many of them making peanuts. They have what seems like 3/5 of a young cheap rotation with Houck/Bello/Crawford and for 2025 Giolito can slide in to the 5th spot. Add Burnes to the front of that rotation and we really may have something great there. Plus if they go over the LT for 2025 you can chop of Giolito's 20 or so Mil and duck back under if they want or even so have that $20M for moves in 2026. 

I agree with almost all of that (short of predicting Burnes will come to Boston; I would only say it's a distinct posibility). But I disagree that it's a question of Henry "changing his mind" about anything. They've always been willing to sign a major contract when they felt it made sense; there's never been a season when that wasn't the case. Just last offseason they were clearly willing to sign Yamamoto to a massive contract. It just didn't happen. And it was only a season before that that they had both Price and Sale still on the books.

And I feel the need to reiterate this, but my prediction is purely conjecture. I understand recent history doesn't do well to back me up, but there is historically precedence for this move and I sprinkled in a little personal desire to my equation as well.  Also, I'm well aware this may not come to fruition. 

Also, they don't have to go big on the FA market for postion players at all this year. Are they going to spend big on a catcher? or a 2nd/ss? or an outfielder? with Mayer/Teel/Anthony knocking on the door?

They easily could sign Burnes for something in the 38-40 million a year range (give or take) and stay under, or worse case scenario be able to reset the year after.

It feels the REAL window for this team may be starting in 2026, but Burnes can kickstart it a year earlier.

I'm also still very optimistic on Crawford and Houck. There recent performances have not turned me sour, I think they're fatigued and I HOPE that they come into next year built up better and continue to perform when they're at the 125-150 IP mark.

Burnes/Houck/Bello/Giolito/Crawford has potential, and I think they could still add more depth to that group as well.

We are so much in agreement on this. We're speaking the same language. I know Crochet is the guy everybody will be looking at and I suspect that one of Anthony or Campbell or less likely Mayer or Teel would go in a deal for him, along with either Sandlin or Arias, plus other, and I suspect that if the Sox dont use their wallets this is the steep direction theyd go in.

Like you I'd rather keep these guys and sign one of Burnes, Fried or Eovaldi. I'm assuming Roki Sasaki isnt coming over yet and if he were he's likely be earmarked for LA.

I'd really hate to gamble talent on Crochet in this era of everybody is soon destined for TJS as soon as they hit 150 innings for a season or two. No thanks. Rather they risk money than talent. I'm not as worried about back end financial contractual efficiency. I ultimately think it would be more costly to replace the talent lost.

And I truly believe that all four of Anthony (I like Abreu but ultimately I much prefer his future to Abreu, who is likely a good platoon player with value), Teel, Mayer, and Campbell (and eventually Montgomery) could all truly impact the Sox for a long time, and I also believe all 5 including Montgomery will be needed. I dont regard them as surplus (I dont see the Sox extending Duran when its time for example and I dont think theyd need to.

If it falls to having to get Crochet I think I'd try to craft a deal around Grissom, Arias, Bleis, and Sandlin, 3 of those 4 guys. I'd have trouble believing that if the White Sox require a pitcher back it would be anybody but Sandlin, but if the Sox think that highly of Sandlin and it took him and highly regarded others to get Crochet, then why do it?

Frankly I dont think the ChiSox would deal Crochet without getting one of the Big 3 or Campbell or even Montgomery.

I know I probably waded too deeply into trade proposals which wasnt my intent, so I'll stop there, but just to talk about how steep a price theyd be paying to invest in a guy with a limited track record of starter success who's demanding a big contract or would not aid his teammates toward the quest of a championship. I'd rather see the Sox open their wallets instead. Get the proven guy instead and let's all reap the rewards of a fruitful farm system producing the most exciting batch of prospects in about a decade.

Between this for Burnes (and that you have to tangle with Boras for 3 to 4 months) and some injury stuff on Max Fried, to me it doesn't feel as super exciting to throw the bag at them as it should be... but there's only so many realistic alternatives.

The pitching pipeline still feels a ways away, and for all we know Bello, Houck, and Crawford could all be under the knife at this point next year. Unless they're willing to trade some of the high upside position players not sure what else there is to do but throw money at the problem