On June 26, the Boston Red Sox lost in embarrassing fashion to the Colorado Rockies, falling to an American League-worst 32-46 and tying Colorado for the worst record in baseball. Now, just 18 days later, the Red Sox find themselves amidst a 14-2 stretch and only half a game back of Minnesota and Seattle for the final wild card position in the American League.

In the blink of an eye, the entire tenor of the season has shifted from a team that was thought to be surefire sellers to potential buyers ahead of the August 3 trade deadline. With few high-level prospects in the upper minor leagues to deal from, could Boston Chief Baseball Officer Craig Breslow choose to dangle a pair of rookie starting pitchers, Connelly Early and Jake Bennett, in potential deals to make a substantial addition to the lineup? 

Both Bennett and Early have performed incredibly well for a Red Sox rotation that has been decimated by injuries at various points throughout the first half of the season. 

Prior to landing on the 15-day injured list with left elbow inflammation, Early posted a 3.44 ERA across 91.2 innings while striking out 9.13 batters per nine innings, the eighth-highest mark among all rookie starters. 

The 25-year-old Bennett has been a revelation for the Red Sox rotation since rejoining it on June 10, allowing only nine earned runs on 26 hits across 37.1 innings while striking out 31 and walking only four. His 2.17 ERA is the 10th lowest among all qualified starters in that span, and his 1.4 fWAR accrued in that time is the fourth highest among all starters.

“Breslow has told Sox people, a team source said, that he believes strongly enough in their ability to backfill that he is OK trading depth pieces, even if they excel elsewhere," Tim Healey of the Boston Globe wrote on June 1, citing trades that sent starters Quinn Preister and Kyle Harrison to the Milwaukee Brewers. 

While neither Bennett nor Early could necessarily be described as 'depth pieces,' and both have had far more major league success than Harrison or Preister, both profile more as back-end starters than as the frontline arm Payton Tolle represents. 

If you need an example of Breslow's ability to backfill rotation depth, look no further than Bennett himself, who went from a relatively unknown prospect when he was acquired over the offseason to a contributor on the hottest team in baseball. 

When looking at potential assets the Red Sox could deal from, there isn't much for the Red Sox to deal from in terms of the deadline's hottest commodity for selling teams: prospects in the upper minors who are close to contributing at the major league level. 

Boston's top two prospects, shortstop Franklin Arias and pitcher Anthony Eyanson, are both with Double-A Portland, but neither is considered 'close' to contributing at the major league level. 

Along with the fact that Early and Bennett are already contributing at the major league level, they are also among the most valuable assets in baseball, young, controllable starting pitching, coming with four and six years of control, respectively. 

The Red Sox find themselves in a mess of teams in the American League playoff picture. Their path ahead of the deadline is still to be determined, but if they choose to be buyers, they will need to be strategic about how they do so, adding pieces that can contribute beyond just the 2026 season.

Given that both Early and Bennett are contributing at the major league level and have significant team control, their values should be high on the open market, giving Breslow an opportunity to balance the roster by adding a bat with multiple years of team control in a potential deal. 

If the Red Sox are looking to make meaningful upgrades to the lineup for 2026 and beyond, dealing from their strength, the starting rotation, may be the only way to accomplish that. 

The MLB Trade deadline is August 3 at 6:00 p.m. ET. 

Remember to join our RED SOX on ROUNDTABLE community, which is FREE! You can post your own thoughts, in text or video form, and you can engage with our Roundtable staff, as well as other Red Sox fans. If prompted to download the Roundtable APP, that's free too!