How Boston Built a Rotation from the Bargain Bin
Photo by Matthew J. Lee / Boston Globe Staff
Diehard Red Sox fans have seen the first half of the season go completely sideways in almost every visible way possible, leaving many of them weeping in their Dunkin Iced. After the unceremonious dismissal of Alex Cora and several other key members of the coaching staff, on top of a series of other blunders since then, the predicament CBO Craig Breslow created has genuinely left his job on the line. As of June 14, the Sox occupy the bottom of the AL East with a 29-40 record, but there remains one corner of the operation where things are going right.
With the help of pitching coach Andrew Bailey, front office pariah Breslow has been pushing his chips all-in on a pipeline of southpaws since day one - not just as the future of the team, but also his future with the organization. While the rest of baseball builds its pitching arsenals by splashing out big checks, the Red Sox have quietly built something much cheaper - a cadre of developing lefty arms and at least one shrewd value trade - and it just might be their best-kept secret.
Despite spending $170 million on All-Star Garrett Crochet, they’ve watched him post a 6.30 ERA this season before landing on the IL in late April. There’s no timeline on his return after he suffered another setback that put him on the 60-day IL with a lat strain, and even he’s claimed, “it is a lot worse than we thought.” However, a bright spot is that Breslow and co. struck a subsidized steal for the rotation’s steadiest arm, Sonny Gray, getting the Cardinals to eat $20 million of his salary. More importantly, they’ve been developing big-framed prospects, namely Payton Tolle, Connelly Early, and Jake Bennett, who are breaking into the starting rotation and beginning to deliver ROI.
Tolle has been throwing high-quality stuff since his electric debut against PIT last season. Although he started this season at AAA Worcester due to a crowded rotation, he got the call-up when Gray got injured. In his 2026 debut, he became the youngest pitcher to go six innings, allow one or zero runs, and register at least 11 strikeouts versus the Yankees in 14 years - with Chris Sale in 2012, and before him, Smoky Joe Wood in 1911 the only others to do it that young against the Bronx Bombers. Overall, he’s had a nine-start stretch, posting a 2.70 ERA, 1.05 WHIP, and 54 Ks in 53.1 IP, leaving NBC Sports Boston to call him “a breath of fresh air amid a dreary season.” A rough June 9 start against Tampa Bay brought him back to Earth, but that simply demonstrates he’s human. On the whole, he remains solid and is redefining what this rotation can be without its ace. He’s also established himself as a fan and clubhouse favorite after his USA-themed presentation in front of the whole team in February - featuring Joey Chestnut as the “Sultan of Sausage” - lighting up social media.
Connelly Early 2026 Percentile Rankings (Baseball Savant)
Early, the youngest Sox postseason starter since Babe Ruth in 1916, earned a 2026 starting slot after spending his 2025 season lighting up Double-A Portland and Triple-A Worcester ahead of his call-up, going on to post for Boston a 2.33 ERA, 1.09 WHIP and 29:4 K:BB over 19⅓ innings, including a playoff appearance. So far this year, he’s had 14 starts, 75.2 IP, and a 3.81 ERA. His most recent start on June 14 against Texas underwhelmed, with Wyatt Langford’s leadoff homer over the Monster illustrating that the process metrics - including Hard-Hit %, Barrel %, and Average Exit Velocity allowed, all bottom quartile - say keep an eye on him and stay patient as he matures through his developmental phase.
Photo by Maddie Meyer / Getty Images
6’6” Bennett is the exclamation point on the Red Sox pitching story. After a Tommy John detour, he joined the team through a swap with the Nationals for Luis Perales, making his debut on May 1 vs. Houston. He then suffered a rough second start, after which he was optioned to AAA Worcester, where he ran a clinic of 11 strikeouts against the Rochester Red Wings on May 20, and has racked up a 1.49 ERA, 1.02 WHIP, 41:9 K:BB over 42.1 IP across 10 starts. He got the call back up on June 10 to try to stop a sweep by the Rays, registering 5 IP, 4 ER on 7 H, 1 BB, 4 K - though 10 whiffs on 73 pitches (52 for strikes) suggested the final line oversold how he actually pitched. For a guy who’s been up, been down, and back up again, he’s entered the conversation as one of the guys knocking on the door hard for an MLB breakout.
None of this is enough to overcome the dumpster fire that is the Sox 2026 season, but it’s a stable foundation for whenever the front office sorts out its bigger issues. With three big southpaw names in the Sox pipeline, if even two of these guys break out while Crochet is sidelined for the foreseeable future, how does the story of the Red Sox rotation flip?
John D Connolly is a lifelong Red Sox fan now living in Edinburgh, where first pitch usually collides with last call. He writes about the Sox, player development, and the thin statistical excuses that keep fans believing. Find him on X at @jdconnolly.