Former MLB GM Reveals Where Red Sox Stand Ahead Of Uncertain Trade Deadline

Former MLB GM Reveals Where Red Sox Stand Ahead Of Uncertain Trade Deadline originally appeared on NESN . Add NESN as a Preferred Source by clicking here . The MLB trade deadline is still over two months away, but many baseball fans and analysts are already wondering what the Boston Red Sox will do.

Last year, they were clear buyers, adding Dustin May and Steven Matz to bolster their pitching staff. This year is more uncertain , however, with the Red Sox currently last in the AL East at 20-27. Fortunately, the American League is incredibly weak this year, which has helped Boston stay in contention despite its sluggish start.

If the Red Sox turn their season around or stay in the hunt for a playoff spot, they will likely look to add at the deadline, per Craig Breslow's recent comments . If they continue to struggle and fall out of the race, however, they may need to sell and start positioning themselves for next year. Where all 30 MLB teams stand and their trade deadline outlook at the quarter mark https://t.

co/bLLFr4Lhr2 via @NYTimes — Jim Bowden⚾️ (@JimBowdenGM) May 19, 2026 "The Sox have the pitching to stay in the race but have an awkward roster on the position player side with strong needs for an impact middle-of-the-order bat and an upgrade at third base," former MLB GM Jim Bowden wrote for The Athletic on Tuesday (subscription required). "If they can keep themselves close to a playoff berth, they could be buyers and they have the prospect talent to make some deals. However, they also could sell or balance the approach by trading a major-league outfielder for a major-league infielder of equal value.