Jake Bennett

Analysis
Bennett pitched well during the 2025 season in his first year back since Tommy John surgery, posting a 2.56 ERA and 1.13 WHIP with 33 strikeouts across 45.2 innings at Double-A. He's yet to pitch above the Double-A level, so it wouldn't be a surprise to see him begin the 2026 campaign in Portland now that he's joined Boston's farm system. Chief baseball officer for the Red Sox, Craig Breslow, is clearly high on the southpaw. "We feel like Bennett is a high probability starter that excels in some things that are hard to teach," said Breslow, per Chris Cotillo of MassLive.com. "Fastball playability driven by above average extension and strike throwing ability. His whiff rates and ability to manage hard contact have us confident in his ability to be a major league starter."