For the Red Sox, it is a time of what-ifs. And as their 9-7 loss to the Rays on Tuesday night underscored, one of the biggest counterfactual hypotheticals relates to the road almost, but ultimately not, taken in building the rotation last winter.
The Sox identified righthander Zach Eflin as one of their top free-agent targets. Though injuries limited Eflin to 180 innings with the Phillies in 2021-22, the Sox believed the 28-year-old (who turned 29 in April) had the ability to carve the strike zone with a wide variety of pitches and take a step forward as a starter. In Philly, he’d done a terrific job of limiting both walks and hard contact, and he had a repertoire that suggested the potential to boost his strikeout numbers.
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“We liked the stuff. We liked the strike-throwing ability,” said Sox manager Alex Cora. “We talked about keeping him healthy, that was one of the question marks coming into the season. . . . We felt like he was going to be — and he is — a very good pitcher, very versatile. He can move the ball around with different fastballs.”
The Sox were among the most aggressive in pursuing the righthander, and felt close to a deal with a three-year, $40 million offer. But Eflin, an Orlando-area native, instead elected to sign with his hometown Rays for those same terms in early December.
“It just didn’t work out. We felt like were there right at the end, and he made a decision to stay in Florida,” said Cora. “It just didn’t happen.”
The Sox ultimately signed Corey Kluber to a one-year, $10 million deal. The Sox went 3-6 in Kluber’s nine starts before demoting the veteran to mop-up duty; his season ultimately concluded with a 7.04 ERA, the seventh-worst mark in the game by a pitcher who threw at least 50 innings this year.
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Eflin, meanwhile, has been the Rays’ rotation constant, and most likely will be their Game 1 starter in the postseason. On Tuesday against the Sox, after the Rays lineup ambushed Tanner Houck for seven runs in three innings, Eflin delivered yet another solid performance.
He breezed through four shutout innings before stumbling in the fifth, while he was dealing with an apparent finger issue that required a trainer’s attention. Though Eflin gave up a three-run homer to Enmanuel Valdez, he still left with a healthy lead in hand.

Eflin improved to 16-8 with a 3.50 ERA. He leads the American League in wins, ranks second in the league in both WHIP and walk rate, and ranks among league leaders in starts of at least five (27) and six (19) innings. The Rays are 23-8 in his starts, tied for the second most wins behind any starter in baseball this year.
Surely, the Sox would be in a better position — both in 2023 and beyond — had Eflin been a part of their rotation. Might he have made enough of a difference for them to still be in contention? It’s fair to wonder whether Eflin would have enjoyed the same success on a Red Sox team with the worst defense in baseball, but they certainly wouldn’t be far off a contending pace.
“I don’t have a crystal ball,” said Cora. “I’m not that smart to say [his 2023 breakout] was going to happen, but we did feel like he was going to be a good one.”
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Though the Red Sox have spiraled towards embarrassment down the stretch, they might not have been much more than a single decision away from a season that would have been respectable, and perhaps better than that.
Eflin was hardly a marquee name on last year’s free-agent market, yet he’s been one of the most impactful pitchers from that class. Certainly, the Sox need to pursue starters with the ability to front a rotation, but the most successful organizations often identify and develop pitchers into such roles, rather than relying on (and simply paying for) pedigree.
Houck, a pitcher they have developed, allowed the first six Rays of the game to reach base Tuesday. He hit the leadoff man, saw one batter reach on an error, and gave up four hits in falling behind, 3-0. The Rays jumped him for four more runs in the third, leaving the Sox too big a hole to escape, though they stubbornly attempted the climb.
“Terrible,” Houck said succinctly of his performance.
René Pinto clears the wall and the @RaysBaseball take a 7-0 lead! 😤 pic.twitter.com/Y8Qmy0AzPe
— Bally Sports Florida & Bally Sports Sun (@BallySportsFL) September 27, 2023
Valdez added an RBI double to his homer, giving him a career-high four knocked in.
After Houck (5-10, 5.31) departed, reliever Zack Kelly — in his first big league appearance since a frightening elbow injury on April 12 that ultimately required ulnar nerve transposition revision surgery — tossed a scoreless fourth inning.
Kelly’s appearance set in motion a run of four scoreless innings by the Boston bullpen, allowing the Sox to rally within one run at 7-6 through seven innings. But the Rays scored twice more in the eighth off Chris Murphy and Josh Winckowski to put the game out of reach.
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Alex Speier can be reached at alex.speier@globe.com. Follow him @alexspeier.