It might seem like the Boston Red Sox messed up their offseason plan, and to some degree, one could argue they did. But it's surprising, in hindsight, how little trade value they gave up.
Trades were a huge piece of the Red Sox's offseason strategy. They swung an early move for Sonny Gray, upgraded their offense with Willson Contreras, and finished the offseason with the surprise six-player deal for Milwaukee Brewers infielders Caleb Durbin and Andruw Monasterio.
With one notable exception, the Red Sox really didn't wind up giving up players who would go on to start their 2026 seasons with major wins above replacement outputs. We went through every offseason transaction, and these have been the five most valuable players for their new teams, sorted by bWAR (though fWAR is almost identical in most cases to this point).
1. Kyle Harrison (1.2 bWAR)
The most obvious "blunder" of the offseason for chief baseball officer Craig Breslow was shipping out Harrison, who now owns a 2.41 ERA and 41 strikeouts in his first 33 2/3 innings as a Brewer. It was a trade hardly anyone doubted at the time, given Harrison's spot on the rotation depth chart at the start of spring training, but it's now more evidence that Milwaukee almost always knows something other teams don't about pitching.
T-2. Brennan Bernardino (0.3 bWAR)
Bernardino was dealt to the Colorado Rockies for Braiden Ward, the major league leader in spring training stolen bases. It's a deal Boston would probably make again, considering how enticing Ward could be as a pinch-runner if nothing else, but Bernardino has been his usual reliable self on the steadily improving Rockies and would probably be an upgrade over the likes of Danny Coulombe
T-2. David Hamilton (0.3 bWAR)
Hamilton has a .574 OPS and no home runs for the Brewers, so in other words, he'd fit right in offensively if he had remained in Boston. But he steals bases and plays solid defense at multiple infield positions, so WAR still grades him as a positive player, if only barely.
T-4: Vaughn Grissom, Tristan Gray, Shane Drohan (0.1 bWAR)
Grissom was about to become a 40-man roster casualty, and his hot start for the Los Angeles Angels has already begun to fizzle (.530 OPS in May). Gray was someone the Red Sox might have regretted kicking off the 40-man, but he's been so-so thus far for the Minnesota Twins. And, of course, the third member of the Brewers trade had to sneak his way into the picture, as Drohan has a 3.38 ERA in 16 innings.