Red Sox’s Craig Breslow Could Regret 2 Trades, MLB Insiders Say

Much has been written about Boston Red Sox chief baseball officer Craig Breslow and his work ahead of the July 31 MLB trade deadline.

He completed a deal with the Los Angeles Dodgers just before the 6 p.m. ET deadline for pitcher Dustin May. Breslow sent a pair of prospects to the Dodgers, including right fielder James Tibbs III. And that’s a deal the Red Sox could end up regretting.

“Tibbs was a first-round pick of the Giants in the 2024 draft but has already been traded twice since then, once in the Rafael Devers trade earlier this season and now again in the May deal,” ESPN’s Kiley McDaniel wrote Friday.

“He’s a classic right fielder with power-and-patience and 25-homer upside, though he isn’t the biggest or most athletic player, so there isn’t a ton of margin for error in that projection,” McDaniel concluded.

“Rival executives believe the deal could be a steal for the Dodgers with Tibbs having a chance to become a star,” USA Today’s Bob Nightengale reported Sunday.

Tibbs was Boston’s No. 5 prospect at the time of the trade. And here’s the rub: Breslow flipped him for a pitcher (May) who will be a free agent following the season.

But that might not be Breslow’s biggest regret.

“On April 7, Milwaukee made a seemingly minor deal with Boston for Quinn Priester, who since then as a starter or bulk reliever was 10-2 with a 3.27 ERA and Milwaukee had won the past 11 games in which he pitched,” the New York Post’s Joel Sherman noted Saturday.

The Red Sox acquired Priester, 24, from the Pittsburgh Pirates before the 2024 trade deadline. He made one start for the Red Sox last year, giving up one run in five innings of work in a 3-1 win over the Tampa Bay Rays on the final day of the regular season.

In April, Boston shipped him to the Brewers for minor-league outfielder Yophery Rodriguez and minor-league right-hander John Holobetz.

Rodriguez, 19, has played in 80 games for High-A Greenville, hitting .225 with five home runs and 36 RBIs.

Holobetz, 23, also is playing for High-A Greenville, where he’s 4-2 with a 3.43 ERA in 12 games (11 starts).