These Four Players Hold the Keys to Red Sox's Trade Deadline Plans

In a turn of events that was so improbable Hollywood would have rejected the script just a month ago, the Boston Red Sox have rattled off a 13-game winning streak and are firmly in the American League Wild Card picture. After sweeping the first series of the second half against the Tampa bay Rays, they certainly have their eye on continuing the hot streak as we progress through the end of July. If things keep up on this track, then Craig Breslow will be keen to add pieces as the trade deadline approaches. That happening though, hinges on these four players not buckling under the pressure that leading a playoff-bound team comes with. 

#4: 3B Caleb Durbin

Who would have thought that after the first two months of the season, Durbin would be looked at as a make-or-break player. After a couple of days off in late May, he has been on a tear at the plate. He’s currently slashing .236/.299/.392 with a .304 wOBA, 89 wRC+, and a 1.4 fWAR. While the slash line doesn’t look overly impressive, remember he was hitting well below the Mendoza line for weeks when the season got underway. He’s been Gold Glove worthy at third base on defense all year, and now that his bat is finally coming around, he’s one of the most valuable pieces on this team. While he’s not a pure power threat, he can drive the ball out of the yard with relative ease. His strength lies in his ability to get on base though, and while we’d like to see a higher walk rate than his current 6.6%, we’re not going to complain too hard. A couple of months ago, we hosted a livestream of the Talk Sox Podcast with Brewer Fanatic’s Jason Wang and Jake McKibbin. During it, Jake told us that we’d love Caleb Durbin eventually this season. At the time we thought he was crazy -- now, we’re finding out that Brewers fans are just as prescient as the team they root for.

#3: LHP Payton Tolle

It may feel a bit weird to include the rookie southpaw on this list, but he essentially plugs in as the number three starter for this team and needs to remain rock solid on the mound as he prepares to fly past his career high in innings. Tolle currently holds a 3.11 ERA with over 84 innings pitched with a strikeout percentage of 25.5%, a walk rate of 7.3%, a 3.23 FIP, and 2.1 fWAR. He had a couple of shaky starts this season and for the first quarter of the year, the offense seemed allergic to letting him win games when he was on the bump, but we seem to be beyond both issues at this point.

Where the pressure lies for the youngster is in his pitch mix. He throws the ‘Three-Headed Monster of Hard’ with his fastball combination of a four-seam, sinker, and cutter, but when he’s operating at his full capacity, he’s featuring a devastating curveball that keeps hitters off balance and off rhythm. If he continues to be the dominant starter we’ve come to expect, then the biggest strength of the Red Sox will continue to propel them forward. If he runs into a second half wall, though, then it could be tough sledding for an injury-depleted starting rotation.

#2: OF Wilyer Abreu

We all expect Abreu to play Gold Glove defense in right field on a daily basis, but the steps he’s taken against left-handed pitching for the 2026 season have shown us just how special of a player he can be. Against southpaws in 2026, Abreu is slashing .345/.421/.527 with a .411 wOBA, and 162 wRC+. To put it simply, he’s been incredible against them. When facing a righty though, the numbers look vastly different. He’s slashing .227/.295/.406 with a .303 wOBA, and an 88 wRC+.

To be able to help push the team in the right direction as they look to buy heading into the trade deadline, Abreu has to find his footing against righties moving forward. Luckily, he seems to have maybe done that early in the second half as he took Griffin Jax deep for two home runs in the first game back out of the All-Star Break. 

#1: 1B Willson Contreras

The heartbeat of the offense, the leader on the field. Contreras has been as advertised since being brought over from the Cardinals. The Sox played great baseball while he was suspended for the altercation he was a part of against the Nationals, but the team goes as Contreras goes. When he slumps, it seems like the rest of the lineup is slumping. When he’s hot, as he’s been much of this season, everything in front of and behind him seems to click.

On top of being an excellent offensive player, Contreras has settled first base in a way that hasn’t been seen in years in Boston. He’s smooth, picks anything near him, and now we no longer have to worry about the cold corner being a defensive black hole. As long as he continues to play well on both sides of the ball, the Red Sox are going to be in a great spot as we approach the trade deadline.