THE BILL COMES DUE
Part 2: Craig Breslow and the Unraveling of the Boston Red Sox
The 2026 Boston Red Sox were supposed to be different. Garrett Crochet coming off an AL Cy Young runner-up season. Ranger Suarez freshly signed for five years and $130M. Sonny Gray, Johan Oviedo, and a rotation that Breslow spent three offseasons and significant organizational capital constructing from scratch.
Sam Kennedy said there was no ceiling. As it turns out, there was. The Red Sox hit it sometime around Memorial Day.
Boston is 27-39, 12 games under .500 in June for the first time since 1997. The manager is gone. The ace cannot throw a baseball and has no idea when he will be able to. And the most damning data point of the season: the Red Sox are 0-36 when trailing by three runs at any point in a game.
Not one comeback. Not one stolen win. Not one night where somebody played hero and Fenway went home happy.
That is not a slump.
That is a broken team.
The Rotation That Wasn't
The entire identity of the 2026 Red Sox was run prevention. Breslow built his offseason around it, signing Suarez and acquiring Gray and Oviedo to surround Crochet with enough quality that the staff could carry the team even when the offense sputtered.
Instead, Oviedo made only one start before his elbow injury, surrendering four earned runs over 3.2 innings against Houston. At this point, his Red Sox tenure has lasted roughly as long as NESN’s free trial.. Gray has been limited by injury throughout the season. And Crochet, the $170 million centerpiece, has not pitched since April 25. Before landing on the IL, he posted a 6.30 ERA and 1.47 WHIP across 30 innings, numbers that would have been alarming even if he had stayed healthy. Crochet told Peter Abraham of the Boston Globe that his lat strain "is a lot worse than what we thought" and replied, "I have no idea," when asked when he might be cleared to throw again.
The one exception has been Suarez. His 2.44 ERA and 0.95 WHIP have made him one of the most effective pitchers in the American League. The problem is that one successful acquisition cannot carry an entire run prevention strategy by itself. Baseball stubbornly insists on using more than one pEvery good team needs young players to emerge. Few expect a rookie to arrive and immediately start cleaning up after an offseason built around veteran pitchingitcher.

When the second, third, and fourth starters are unavailable, and the ace is in the dugout with no throwing program, the identity collapses entirely. The 2026 Red Sox were built around pitching. By June, they were running out of pitchers.
Payton Tolle, Breslow's second-round pick in 2024, has been a quiet bright spot with a 2.61 ERA in seven starts. He is 23 years old, costs next to nothing, and is currently one of the better starters on the roster. That organizational win belongs to Breslow.
The problem is that when a 23-year-old rookie becomes one of the most reliable parts of your rotation, it usually means something has gone very wrong everywhere else. (lets change this line to something else)

The Coaching Purge: Two Years Late, Zero Plan
On April 26, 2026, the morning after a 17-1 win over Baltimore, Breslow fired Alex Cora along with hitting coach Peter Fatse, bench coach Ramon Vazquez, third base coach Kyle Hudson, assistant hitting coach Dillon Lawson, and hitting strategy coach Joe Cronin. Chad Tracy, Triple-A Worcester's manager, was named interim.
The timeline is difficult to reconcile. According to reporting from the Boston Globe and Sports Illustrated, Breslow wanted to make coaching changes after the 2025 season. Cora made clear he would resign if those changes were forced. Breslow backed off and brought the same staff back for 2026. Then, 27 games into a contract he had personally extended through 2027 at $7.25 million annually, he fired everyone. Players were notably upset. Trevor Story, who has struggled to justify his own contract for much of his Red Sox tenure, described Breslow's address to the clubhouse as unsatisfactory.
If the staff was the problem, why bring them back? If they were not the problem, why fire them 27 games into the season?
More concerning than any individual decision is the pattern.
The Devers situation ended in a trade. The coaching dispute ended in mass firings. Jason Varitek, the franchise captain and one of the most respected figures in the organization, was officially "reassigned" to a role that was never announced.
When asked directly, Breslow told WEEI, "There is a place in this organization for him for as long as he wants it."
Apparently that place remains undefined.
The Red Sox have been remarkably consistent in one area under Breslow: every major disagreement seems to end with someone leaving.
Organizations survive bad trades. They survive bad free-agent signings. What they struggle to survive are repeated breakdowns in communication and trust.
At some point, the individual incidents stop looking isolated and start looking like a leadership problem.
How the Red Sox Turned Rafael Devers into Caleb Durbin
This is the part that requires following the thread from the beginning.
In June 2025, Breslow traded Rafael Devers to San Francisco. The most valuable piece of the return appeared to be Kyle Harrison, a 23-year-old left-hander with years of team control and legitimate upside.
Harrison pitched 12 solid innings for Boston before Breslow traded him that offseason, along with Shane Drohan and David Hamilton, to Milwaukee for infielder Caleb Durbin, infielder Andruw Monasterio, catcher Anthony Seigler, and a draft pick. Breslow described Durbin as a key piece in addressing Boston's need at third base.
Here is where things stand today.
Harrison is 7-1 with a 2.72 ERA, 77 strikeouts, and a 1.16 WHIP across 59.2 innings for Milwaukee. At 23 years old, he looks every bit like the controllable young starter Boston believed it was acquiring from San Francisco.
Durbin is hitting .204/.264/.330 with a .594 OPS and a 61 wRC+, production that ranks among the least effective of any qualified hitters in baseball.
Devers became Harrison. Harrison became Durbin.
On paper, it's a sequence of transactions. In practice, it's a cautionary tale.
The original Devers trade was controversial. The Harrison trade is what transformed it into an organizational headache.
Three transactions. One chain of decisions.
And somehow the most valuable player in the entire sequence currently pitches for the Brewers.

Find It. Lose It. Repeat.
There is a recurring pattern in how Breslow handles value he creates. He finds it, and then he does not protect it.
He acquired Carlos Narváez for essentially nothing in November 2024. Narváez responded by hitting .273 in 2025, posting 2.5 WAR, ranking among the American League's best defensive catchers, and earning the nickname "The Captain" from teammates.
Then 2026 arrived.
Boston chose to carry three catchers. Narváez lost his role. He later said publicly that nobody had explained the decision to him. One of the team's better value stories went from everyday contributor to third-string catcher without so much as a conversation.
The story feels familiar.
Tyler O'Neill arrived for almost nothing, hit 31 home runs, and left for Baltimore on a contract Boston could have matched. Alex Bregman signed, played well, and left after one season. Rafael Devers was the face of the franchise until a dispute over his role ended with a trade.
Different players. Different circumstances. Same ending.
At some point, it stops feeling like coincidence.
Breslow has shown a legitimate ability to identify talent and uncover value. The harder question is why so much of that value keeps leaving the organization shortly afterward.
The acquisition part has often been impressive. The sequel has been considerably less successful.

The $/WAR Verdict
The numbers tell the story cleanly.
Free Agent
$ Paid
WAR Delivered
$/WAR
Lucas Giolito
$37M
2.5
$14.8M
Liam Hendriks
$10M
0.3
$33M
Walker Buehler
$21M
0.5
$42M
Patrick Sandoval
$18.25M
0.0
—
Alex Bregman (1 yr)
$30M effective
3.5
$8.6M
Ranger Suarez (yr 1)
$26M
1.8 pace
TBD
Total
~$142M
~8.6 WAR
~$16.5M/WAR

Market rate is roughly $9 million per WAR. Boston spent $142 million on free-agent pitching and received roughly six wins above replacement in return. At market value, that same investment should have produced about 15.
That missing value does not exist in a spreadsheet. It exists in the standings.

The Full Report Card
Category
Grade
Free Agent Pitching
D
Free Agent Position Players
C
Trade Value Acquired
C-
Trade Value Surrendered
D-
Draft (Breslow era only)
B
Pitching Infrastructure
B-
Farm System Stewardship
C
On-Field Results (Breslow contribution)
D
Player and Org Navigation
D-
Managerial Decision-Making
D
Overall
D+

The Question That Remains
On June 11, Sam Kennedy went on the radio and said what everyone already knew.
"There's no way to sugarcoat it. It's been awful."
He also confirmed that Craig Breslow is not being fired.
That is ownership's prerogative. But the argument for Breslow's continued employment increasingly rests on ideas and intentions. The argument against him rests on outcomes.
The Devers situation ended in a trade. The coaching dispute ended in mass firings. The Varitek situation remains unexplained. Free-agent pitching investments fell well short of expectations. Players have publicly questioned communication. The roster has gotten more expensive, older, and worse.
None of these decisions exist in isolation. Together, they form the record.
At some point the question stops being whether Breslow's vision is sound and starts being whether a front office executive who cannot consistently execute that vision deserves additional runway.
Building a pitching culture is valuable. Identifying talent is valuable. Having a plan is valuable.
Eventually, however, executives are judged on results.
The bill has come due.
And right now, the ledger is not in Breslow's favor.