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Inside The Red Sox

Red Sox's Biggest Mistakes on Full Display in Braves-Brewers Matchup

Sometimes, the stars align
May 28, 2026; Boston, Massachusetts, USA; Atlanta Braves starting pitcher Chris Sale (51) pitches against the Boston Red Sox during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
May 28, 2026; Boston, Massachusetts, USA; Atlanta Braves starting pitcher Chris Sale (51) pitches against the Boston Red Sox during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

Sitting at 30-43 on the season, the Boston Red Sox don't have a lot of time for scoreboard watching. But some members of the organization could find it hard to look away from one out-of-town game on Saturday.

At Truist Park, the Atlanta Braves will host the Milwaukee Brewers for the second of three games between National League division leaders. And the two starting pitchers are both left-handers who have played huge roles in getting their teams off to strong first halves of the season.

It just so happens that both of those lefties were traded away in the last three years by Red Sox chief baseball officer Craig Breslow. One is a decorated veteran who won a Cy Young Award immediately after leaving Boston in Chris Sale; the other is Kyle Harrison, who is enjoying a breakout season after struggling to crack the Red Sox's rotation last year.

Sale, Harrison about to square off in Atlanta

Harrison
Jun 14, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Kyle Harrison (52) throws a pitch during the first inning against the Philadelphia Phillies at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images | Jeff Hanisch-Imagn Images

As the Red Sox's season remains on life support at very best, Sale and Harrison are perhaps the two toughest watches around the league. The Red Sox's rotation has been solid this season, but either of these two would be the ace on the current iteration of this Boston team.

Sale is in his third year after leaving the Sox, and has done nothing but shove the entire time. He's got a 2.43 ERA and has racked up 12.5 bWAR in his 63 appearances with the Braves, which is more bWAR than he put up in the finals six years of the contracts he signed with the Red Sox.

Harrison, meanwhile, owns a record of 8-1 and a 2.47 ERA through 13 starts this season. At the time the Red Sox traded him, his major league ERA was 4.39 through 194 2/3 innings. Suffice it to say, Boston didn't see this breakout coming.

What hurts the most for the Sox is that both of these trades were totally defensible at the time they were made. Sale only had one year left under contract and looked as though he couldn't stay healthy, while the Red Sox thought they were getting a future starting infielder in Vaughn Grissom (now with the Los Angeles Angels). Harrison wasn't going to crack the rotation out of spring training this year, while Caleb Durbin (.609 OPS in Boston) looked like a surefire asset at third base.

Moral of the story: Just look away from the action at Truist on Saturday.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@moreviewsmedia.com