Four Free Agent Fits for the Middle of the Red Sox's Rotation

[Jordan Leandre]

It's not sexy to talk about rotation depth, but it often proves just as conducive to winning as having top-shelf talent.

The Boston Red Sox enter the 2025-26 offseason in a fascinating position: They already have a ton of organizational depth for the rotation. Looking at the youth on the precipice of big-league readiness, they have left-handers we saw briefly in Payton Tolle, Connelly Early, and Kyle Harrison, as well as right-handers Hunter Dobbins and Richard Fitts. They also have Luis Perales and David Sandlin residing in Triple-A Worcester, both of whom were at least discussed as potential break-glass-in-case-of-emergency options at the tail-end of the 2025 season.

Then, you get into the veterans this team has coming back. Right-hander Kutter Crawford, who made 56 starts between 2023 and 2024, missed all of 2025 and is set to return next season. There's also left-hander Patrick Sandoval, who looked like a potential All-Star with the Angels as recently as 2022.

With all of that in mind, one can argue the Red Sox have enough depth, but not enough elite-level talent behind ace left-hander Garrett Crochet. And it's true to a degree—the front of the rotation needs to be a priority.

However, ignoring the middle of the rotation would be irresponsible for third-year Chief Baseball Officer Craig Breslow. While depending on Early, Dobbins, or Tolle isn't a bad strategy (depending on health), having them as Plan B would make the organization stronger. Not only that, but for the Red Sox to add someone at the top of the rotation, they may have to dip into all of this depth to acquire an ace on the trade market.

So, if the Red Sox do pursue a lesser starting pitcher in free agency, who should they target?

1. RHP Lucas Giolito

The obvious candidate here is to re-sign the right-hander who just spent two years in the organization. While the finish to his season was sub-optimal, there was a lot to like about Giolito's 2025 campaign.

For starters, he pitched deep into games. In his 26 starts, he got at least one out into the sixth inning 16 times, the seventh inning seven times, and the eighth inning three times (completing eight twice). His strikeout-to-walk numbers left a bit to be desired, as did his under-the-hood metrics, but it's hard to argue against a 3.41 ERA in 145 innings.

There's logic to letting the 31-year-old be one-and-done in Boston, similar to when the organization decided to make Michael Wacha a one-and-done project after 2022. However, Wacha went on to maintain success for the San Diego Padres and Kansas City Royals. While the logic was sound then, and would be now, that thought may linger on the minds of remaining Red Sox brass from that era.

If they're going to add someone in this tier of starting pitcher, Giolito probably makes the most sense given the familiarity both parties have.

2. RHP Zach Eflin

The Red Sox had Eflin on their radar ahead of the 2023 season, before he shockingly signed the richest free-agent contract in Tampa Bay Rays history.

While the 2025 season was nothing short of disastrous for the right-hander, injuries played a major role. From 2023 to 2024, the 31-year-old posted a 3.54 ERA, a 3.37 FIP, and a 19.6% strikeout-minus-walk rate in 59 starts between the Rays and Baltimore Orioles. However, 2025 was a bad year for him; his ERA skyrocketed to 5.93 and his K/9 dropped to 6.31 across 14 starts before his season officially ended in August.

He had a lumbar microdiscectomy in August, which people undergo to remove part, or all of, a bulging or herniated disc in the lower spine. According to reports, he expects to have a normal offseason after the standard eight to 12 weeks of recommended rest and rehab. Back injuries are no joke, though, especially for pitchers. It's hard to not at least expect that to linger more as he gets deeper into his 30s.

That said, he's a talented arm and the injury and his 2025 performance should knock down the acquisition cost. Spotrac gives him a market value of $16.2 million, which is higher than I'd anticipate given early signs this market is showing, including Shane Bieber opting into his $16 million contract with the Toronto Blue Jays. Something in the range of $10 million over one year should feasibly get the job done.

3. RHP Chris Bassitt

From one division rival to another, Bassitt is one of the highest floor guys in the sport. Since 2022, he's made at least 30 starts each year, pitched at least 170 innings, and posted at least 2.3 fWAR.

He's not the same pitcher he was a half-decade ago for the Athletics, but he's the same pitcher in theory as Walker Buehler, except with less ceiling and a higher floor. In layman's terms: He's actively good at pitching, just nearing the end of his career.

*ducks*

Hear me out. He throws eight pitches, which is pretty darned impressive. While half of them registered at under six percent usage, all made up at least 2.7% of his total pitches. He also throws everything to both sides, even though there's a clear skew to one side of the platoon or the other. His cutter, curveball, four-seam, and splitter all kept hitters at bay in 2025, as all four had opponent batting averages of .220 or lower.

He also comes in with a lot of institutional knowledge of the American League East, spending the last three years with Toronto, with whom he played a key role in getting them to a World Series Game 7.

Bassitt isn't a big strikeout-getter, but he keeps the ball on the ground and generally avoids loud contact. His walks are also generally always in check, save for 2024 where his walk rate sat at a career-worst 9.2 percent. Now, adding him would make it even more imperative that Boston improve its infield defense, which should be a priority anyway, but they could do a lot worse on a one-year deal.

4. RHP Justin Verlander

Despite being the ripe old age of 43 (in February), Verlander is coming off of a very solid season for the San Francisco Giants. 

In 29 starts, the right-hander posted a 3.85 ERA and 2.2 fWAR across 152 innings. After coming off the injured list in June, he was razor sharp to the tune of a 3.60 ERA and 3.34 FIP with 8.64 K/9.

It feels like Verlander is becoming an Immaculate Grid legend by bouncing from team to team in the latter stages of his career, but he's still viable for a competitive rotation. While he gives up a lot of fly balls, he's fairly average at missing the barrel and above average at minimizing hard contact.

Additionally, his changeup was a plus offering in 2025, while his slider performed worse than expected. His fastball is nowhere near the level it was in his Detroit days, but Andrew Bailey has no problem telling his starters to not throw the fastball (if it's ineffective).

Lastly, one cannot overstate the institutional knowledge Verlander possesses. He's won rings, personal awards, and just about everything a MLB pitcher can achieve. He'd be the most decorated arm to don the Red Sox jersey since Pedro Martinez and Curt Schilling, even if signing him would give major John Smoltz vibes.

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[Hitch]

We're almost certainty not going to move for these sorts of pitchers. Unless something has gone wrong. Otherwise we would have extended the QO to Gio.

Breslow has said its at the top he's aiming (and likely in a trade), and that the middle to bottom is set.

 

[mvp 78]

If they get a depth piece, it's on a cheap deal. They already have Sandoval, Bello, Tolle, Early, Dobbins, Fitts, Crawford, Criswell and Harrison behind Crochet. If they add a #2, I'm not sure they need to add a depth piece with a price tag higher than 10M AAV. 

[moonslav59]

24 minutes ago, mvp 78 said:

If they get a depth piece, it's on a cheap deal. They already have Sandoval, Bello, Tolle, Early, Dobbins, Fitts, Crawford, Criswell and Harrison behind Crochet. If they add a #2, I'm not sure they need to add a depth piece with a price tag higher than 10M AAV. 

I agree. Adding a depth piece might work, but we have 7-8 guys to give a shot, already. We need a solid #2- or a borderline #1. I'd settle for a borderline 2-3, if we make major strides in adding power bats. (Plural)

I still think a trade is most likely the way to fill that need, but maybe I'm biased by the Crochet, Porcello, Sale, Beckett, Schilling and Pedro trades.

Thinks about it: we've made some bad trades for SP'ers, but most were minor ones. Even the Peavy and Nate trades worked out. What has been the worst major trade for a SP'er we have made in the last 2 decades?

[Malcolm White]

5 minutes ago, moonslav59 said:

I agree. Adding a depth piece might work, but we have 7-8 guys to give a shot, already. We need a solid #2- or a borderline #1. I'd settle for a borderline 2-3, if we make major strides in adding power bats. (Plural)

I still think a trade is most likely the way to fill that need, but maybe I'm biased by the Crochet, Porcello, Sale, Beckett, Schilling and Pedro trades.

Thinks about it: we've made some bad trades for SP'ers, but most were minor ones. Even the Peavy and Nate trades worked out. What has been the worst major trade for a SP'er we have made in the last 2 decades?

There's no need to reinforce the bottom of the rotation--you need optionable young pitchers in those slots to have the flexibility to swap them out if they're overwhelmed.  All set there.

But this "solid #2/borderline #1" guy is hard to find.  Guys with 30+ starts, WHIP >1.25, ERA >3.50:

In the AL (not counting Yankees, who have 4):  Castillo, Woo, Gilbert, SEA.  Ryan, Lopez, MIN. Cameron, Bubic, KC. Skrubal. Hunter Brown. Rasmussen, Tampa. deGrom, Eovaldi, Mahle**, Texas.

NL (Dodgers had five, but only Yamamoto made 30 starts): Matt Boyd, Cubs. Hunter Greene (19 starts), Abbott (29), CIN. Cabrera, MI (26 starts). Peralta, MIL. Sanchez, Suarez**, Wheeler**, PHL.  Skenes. Pivetta. Logan Webb, SF.

A few of them are free agents (Wheeler's intriguing), but to make a trade, gotta find a team with pitching surplus (LAD, NYY--not happening) that badly needs offense. KC, CIN look like best bets.

[moonslav59]

2 minutes ago, Malcolm White said:

There's no need to reinforce the bottom of the rotation--you need optionable young pitchers in those slots to have the flexibility to swap them out if they're overwhelmed.  All set there.

But this "solid #2/borderline #1" guy is hard to find.  Guys with 30+ starts, WHIP >1.25, ERA >3.50:

In the AL (not counting Yankees, who have 4):  Castillo, Woo, Gilbert, SEA.  Ryan, Lopez, MIN. Cameron, Bubic, KC. Skrubal. Hunter Brown. Rasmussen, Tampa. deGrom, Eovaldi, Mahle**, Texas.

NL (Dodgers had five, but only Yamamoto made 30 starts): Matt Boyd, Cubs. Hunter Greene (19 starts), Abbott (29), CIN. Cabrera, MI (26 starts). Peralta, MIL. Sanchez, Suarez**, Wheeler**, PHL.  Skenes. Pivetta. Logan Webb, SF.

A few of them are free agents (Wheeler's intriguing), but to make a trade, gotta find a team with pitching surplus (LAD, NYY--not happening) that badly needs offense. KC, CIN look like best bets.

I'd add Lodolo and others to your list (despite no 30 GS) and might go down as low as Mitch Keller, who is more like a mid to a low #2 or high #3, if you use the top 30 grouped pitchers, but I think several can be obtained without giving up the world. 

I think we gave up a lot for Crochet, but it worked. Now, nobody was sure Crochet could lead the league in IP, so there was speculation on him, but we should be able to add a high #2 via trade.

[mvp 78]

2 hours ago, moonslav59 said:

I agree. Adding a depth piece might work, but we have 7-8 guys to give a shot, already. We need a solid #2- or a borderline #1. I'd settle for a borderline 2-3, if we make major strides in adding power bats. (Plural)

I still think a trade is most likely the way to fill that need, but maybe I'm biased by the Crochet, Porcello, Sale, Beckett, Schilling and Pedro trades.

Thinks about it: we've made some bad trades for SP'ers, but most were minor ones. Even the Peavy and Nate trades worked out. What has been the worst major trade for a SP'er we have made in the last 2 decades?

Worst major trade:

Drew Pomeranz

Joe Kelly (aka the Allen Craig deal)

Worst trades involving pitching leaving:

Lester

Arroyo

Masterson

Sale

Lackey

 

[5GoldGlovesOF,75]

Worst trade for a starting pitcher was Andrew Cashner in 2019. Dombro thought he was beefing up the rotation, grabbing a guy who was 9-3 with a 3.83 ERA and 2.5 WAR in the first half.

But Cashner was so bad they only let him make 6 starts before banishing him to the bullpen. His Boston stint: 2-5, 6.20 ERA, -0.3 WAR. The two pitching prospects the Sox dealt never made it, but Cashner never pitched in the bigs again, either. Blaaaaahhhh....

[mvp 78]

2 minutes ago, 5GoldGlovesOF,75 said:

Worst trade for a starting pitcher was Andrew Cashner in 2019. Dombro thought he was beefing up the rotation, grabbing a guy who was 9-3 with a 3.83 ERA and 2.5 WAR in the first half.

But Cashner was so bad they only let him make 6 starts before banishing him to the bullpen. His Boston stint: 2-5, 6.20 ERA, -0.3 WAR. The two pitching prospects the Sox dealt never made it, but Cashner never pitched in the bigs again, either. Blaaaaahhhh....

July 13, 2019: Traded by the Baltimore Orioles with cash to the Boston Red Sox for Elio Prado (minors) and Noelberth Romero (minors).

[mvp 78]

Prado was still in the Phillies org last season and finally reached AA.

Romero was in the O's org last season and has played several AAA games the past few seasons.

Neither seem on track to ever make an MLB appearance. 

[5GoldGlovesOF,75]

1 minute ago, mvp 78 said:

July 13, 2019: Traded by the Baltimore Orioles with cash to the Boston Red Sox for Elio Prado (minors) and Noelberth Romero (minors).

The cash was even counterfeit -- Monopoly money or moldy slips from Geraldo Capone's safe.

[moonslav59]

56 minutes ago, mvp 78 said:

Worst major trade:

Drew Pomeranz

Joe Kelly (aka the Allen Craig deal)

Worst trades involving pitching leaving:

Lester

Arroyo

Masterson

Sale

Lackey

 

Nice.

Pom Pom did okay year 2, but we needed him more year 1.

Allen Craig was a total bust. Kelly did okay. Lackey did much better.

VMart gave us 2 good years, and masterson had like 2 good years out of 5 with CLE, I believe. (Plus we got Barnes as a comp pick for VMart, if that counts)

Arroyo's deal was a total bust. Sael's too.

 

 

[drewski6]

8 hours ago, Hitch said:

We're almost certainty not going to move for these sorts of pitchers. Unless something has gone wrong. Otherwise we would have extended the QO to Gio.

Breslow has said its at the top he's aiming (and likely in a trade), and that the middle to bottom is set.

 

Agree

[drewski6]

4 hours ago, mvp 78 said:

Worst major trade:

Drew Pomeranz

Joe Kelly (aka the Allen Craig deal)

Worst trades involving pitching leaving:

Lester

Arroyo

Masterson

Sale

Lackey

 

Price goes in bottom category.

[moonslav59]

25 minutes ago, drewski6 said:

Price goes in bottom category.

The one where they threw in Betts?

[drewski6]

Just now, moonslav59 said:

The one where they threw in Betts?

Yes, im one of the ones who think price had trade value after we ate half the contract.  It didnt come to fruition cuz he got paid and sat out covid year, but didnt know that at the time

And verdugo always stunk, ill die on that hill.

[moonslav59]

10 minutes ago, drewski6 said:

Yes, im one of the ones who think price had trade value after we ate half the contract.  It didnt come to fruition cuz he got paid and sat out covid year, but didnt know that at the time

And verdugo always stunk, ill die on that hill.

I though half of Price's contract mae him a net zero trade value, so he was basically a dump at full price.

[drewski6]

6 minutes ago, moonslav59 said:

I though half of Price's contract mae him a net zero trade value, so he was basically a dump at full price.

Basically par value? Ill settle for that. So not a drag on Betts, but not adding value either.

[moonslav59]

3 minutes ago, drewski6 said:

Basically par value? Ill settle for that. So not a drag on Betts, but not adding value either.

I think the Sox demanded it, because they wanted to cut costs in a big way. LAD demanded the break even pay point.

Horrible trade.

My question was directed at only major trades for a SP'er.

Pedro

Schilling

Beckett

(Peavy no so big)

Sale

Porcello

(Nate was not a big deadline package)

Crochet

Are there any bigger packages for lesser pitchers I'm missing?

That's a pretty impressive record.

[drewski6]

5 minutes ago, moonslav59 said:

I think the Sox demanded it, because they wanted to cut costs in a big way. LAD demanded the break even pay point.

Horrible trade.

My question was directed at only major trades for a SP'er.

Pedro

Schilling

Beckett

(Peavy no so big)

Sale

Porcello

(Nate was not a big deadline package)

Crochet

Are there any bigger packages for lesser pitchers I'm missing?

That's a pretty impressive record.

I agree have done well trading for SP'ers.  I dont think the procello trade was big. Was it 1 yr of Cespedes for one year of Porcello?

[moonslav59]

11 minutes ago, drewski6 said:

I agree have done well trading for SP'ers.  I dont think the procello trade was big. Was it 1 yr of Cespedes for one year of Porcello?

True. It was bigger than Peavy and Nate, in terms of who we gave up, but not as big as the others. 

The BIG FIVE:

 

Pedro

Schilling

Beckett

Sale

Crochet

They almost all overlapped, except for the Beckett-Sale gap.

[Hugh2]

The ony way I would want some of those guys signed would be if they traded away one of their current pitchers for an upgrade in the rotation E.G. Bello being traded in a package for Hunter Greene, in which case I'm signing a guy to replace Brayan.  

Otherwise, any signing OR trade should be for a legit #2.  And FWIW on a championship caliber team I consider a legit #2 a pitcher who is good enough to be a #1 on most teams.  Do the Sox think that? well they don't have the best reputation recently although they've built back some equity with Crochet last year but If you take Breslow at his words then they will do just that. 

Breslow has stated the team has plenty of #4 and #5 starters and that they are specifically looking for a guy who is a top of the rotation starter.  Now I suppose that's subjective, we could be sitting here in March listening to the Sox brass talk to us about how Justin Verlander is the greatest pitcher of all time and now he's on our team.