5 Teams With the Most at Stake Leading Up to the Trade Deadline

With the resumption of Major League Baseball after the All-Star Break, all eyes turn to the Aug. 3 trade deadline.

For many teams, there’s no question the path they’re taking. Yet for some, there’s just as much uncertainty now as there was early in the season. Some teams, particularly in the American League, have had to restructure expectations. Injuries play a role in that, as does the general variance that comes in this game.

With two weeks before the deadline, six teams in the AL are within five games of the final playoff spot. In the National League, five teams are within three games.

These next couple of weeks can really make or break a team’s season. Particularly these five. Let’s measure the stakes.

Boston Red Sox

Most of 2026 has been marred by tremendous disappointment for the Red Sox. After entering the year with high expectations, they seemed like they were going to fall well short. Yet, through 98 games, they’re holding on to the AL’s final playoff spot with a 50-48 record.

The first half only looks as “good” as it does because Boston ripped off nine straight wins, including 14 of 16, to end the half. They’d bottomed out at 14 games under .500 twice, with many numbers indicating this could be the worst Red Sox team of the live ball era.

These next two weeks are critical for the Red Sox. In the first half, they went 17-27 at home, two games back in the win column of the Athletics. Prorating that over 162 games positions the Red Sox at a 63-win pace at Fenway Park. On the flip side, they were 29-21 on the road, or a 94-win pace.

Good teams aren’t awful at home, and bad teams aren’t good on the road. The Red Sox happen to be both in 2026, the year of the odd statistic for the organization.

Opening the second half with a 10-game home stand against division rivals, two of which are chasing them in the standings, can help validate their winning streak. Indeed, the Red Sox have already swept the Rays in a four-game set. The Orioles and Blue Jays should be easier competition.

They’ve re-positioned themselves as buyers at the deadline. That said, they’re still only two games above .500. These next two weeks could completely change the trajectory of the organization again.

Detroit Tigers

The Tigers are seven games under .500 after taking two of three from the Angels to start the second half. However, they’re third in the AL with a run differential of +31. Their expected win-loss record is 53-46, but that matters little in the standings.

Unfortunately, they’ve only been consistent in their inconsistency this year. Not having ace left-hander Tarik Skubal for several weeks didn’t help, but their lineup and bullpen have been issues all year long. Despite having the AL Rookie of the Year favorite Kevin McGonigle, Detroit ranks 18th with a 99 wRC+.

Their bullpen is second in blown saves as well despite ranking 11th in ERA.

The writing is on the wall for Detroit, though. We’re all talking about the pending free agency of Skubal and, to a lesser extent, 2025 All-Star Casey Mize. A tough two weeks will seal the Tigers’ fate as sellers, and they’d almost have to move off Skubal specifically.

It’s been a tremendous tenure in Detroit for the southpaw, and who knows if even trading him officially spells the end in hopes he signs a long-term deal. But trading him does guarantee he gets a taste of another organization.

Baltimore Orioles

The Orioles picked up steam going into the break as well, ripping off four straight wins and going 7-3 in their last 10. Then, they started the second half by sweeping the Astros.

Their next challenge is a three-game set against the Red Sox at Fenway. A series win could do wonders in reshaping how they approach the deadline. But Boston is red hot, and Baltimore is five games below .500 on the road this year.

They’ve got a young team still, but they spent a lot of money to poach first baseman Pete Alonso from the New York Mets last winter. At 31, there’s only so much time left to expect greatness out of the power-hitting first baseman.

They also expended a lot of resources to acquire right-hander Shane Baz from their division rival Tampa Bay Rays. Despite that, they’re 18th in starting pitcher fWAR and 15th in ERA. They’re going to need the starters to ratchet it up these next couple of weeks so they can have a chance to acquire another arm by Aug. 3.

It started in Houston. It continues in Boston. Even taking two of three would make a world of difference.

Minnesota Twins

The Twins entered 2026 a team destined for lots of losses. Perhaps some of it falls on the landscape of the AL, but they’ve been a pleasant surprise this season, just two games back of the final Wild Card spot.

These next couple of weeks will be huge for this group. What’s especially important, however, is for the Twins to pick a side with conviction. In order to do that, they need to either bottom out or go on a run, because hovering around .500 all year creates a difficult situation come deadline time.

They’ve got some fun pieces potentially available in a selling situation. Catcher Ryan Jeffers, outfielder Trevor Larnach, and utility man Kody Clemens. Even veteran backstop Victor Caratini should have a market if things get dire for the Twins.

On the pitching side, they’ve navigated not having All-Star right-hander Pablo López all season. Joe Ryan remains his usual dominant self, while guys like Taj Bradley and Connor Prielipp have contributed in bursts. Can the secondary and tertiary guys continue to step up with more consistency in the second half? Or will preseason expectations rear their ugly head and cause for a poor second half leading into the deadline?

Time will tell, but a series loss to the Cubs was not the best way to start.

Toronto Blue Jays

Pinpointing exactly how disappointing the Blue Jays’ season has been so far hinges on where you felt the core of the roster was before the offseason. Ultimately, there’s a reason Toronto was viewed as something of a Cinderella team in 2025, despite pushing the Los Angeles Dodgers to the brink in the World Series.

That said, they had a tremendous offseason. Right-hander Dylan Cease started the All-Star Game; third baseman Kazuma Okamoto has 22 homers and 62 runs batted in through 96 games. However, Vladimir Guerrero Jr. has a 99 wRC+ and just six home runs through 94 games, while 2025 postseason hero George Springer has just 68 games under his belt.

They’ve gone from potential World Series contenders to playoff hopefuls in the span of six weeks. Despite the AL’s inability to put sub-.500 teams away, they’re chasing three teams just to be the first team out of the playoff picture.

It’s hard to fathom they do much selling even if these next two weeks are tough. For their sake, they’re hoping to avoid the situation entirely.

Honorable Mention: San Diego Padres

It’s getting late fast for the Padres, who opened the second half with a series loss to the Royals. They’re not necessarily an “old” team, but they’ve got a lot of money tied into some veterans on the wrong side of 30.

The window is closing fast for San Diego, which needs a big second half out of its young stars — namely Fernando Tatis Jr.

Overall, they have one of the worst wRC+ marks in the league and are 23rd in fWAR among position player groups. Despite a tough first half in the power department, Tatis leads the group with 2.1 fWAR. Xander Bogaerts and Manny Machado are third and fourth, respectively, but both have been below-average bats this season.

The Padres need big second halves out of all three, or they potentially have to start tearing some components of the roster down. Again, they’ve invested a lot into this group, with little to show for it save for a National League Championship Series loss in 2022.