There are less than two weeks to go until the MLB trade deadline, meaning contending teams have some decisions to make in terms of how aggressive they want to be. For a team with World Series aspirations, a big move at the deadline could be the catalyst behind a championship run. But acquiring a top player will come at a significant cost, so front offices will have to assess their biggest needs and just how much they are willing to cough up to complete a trade.
Contending teams will look to shore up any weaknesses on their roster to answer to the burning questions hanging over them ahead of the second half of the season. With that in mind, we’re going to identify the biggest question every contender is facing at this year’s trade deadline, and what they might do to address it.
Tampa Bay Rays
Key question: Do the Rays have enough lineup prowess to compete in October?
The Rays have been one of MLB’s biggest surprises thus far into the season, owning the American League’s best record at 56–41. Tampa finds ways to win games. They don’t score a ton of runs (434, seventh-most in the AL) but they don’t surrender many (415, sixth-fewest in the AL), either. The biggest question facing the team is whether their small-ball approach and their lack of elite offensive production will be enough to get the job done in October. The middle infield is an area the Rays could look to address at the trade deadline, finding some offensive upgrades over the likes of Richie Palacios and Taylor Walls, who own a .679 and .597 OPS, respectively.
New York Yankees
Key question: Can the Yankees get more production from their catchers?
The Yankees have not gotten enough production offensively from their backstops. Austin Wells has had a rough go of things this year, registering a .499 OPS and six home runs in 67 games. J.C. Escarra and Ali Sanchez have both struggled at the plate, too. Upgrading at the position will be an important move for New York if it can find a way to do so. Rockies slugger Hunter Goodman and Twins backstop Ryan Jeffers have been linked to the Yankees as the deadline creeps closer, and a trade for either one would instantly solve the team’s most glaring need. Shea Langeliers would certainly do the trick as well if the A’s can be convinced to part ways with the AL’s starting catcher in the All-Star Game.
Boston Red Sox
Key question: Will Boston’s winning streak convince the front office to be buyers?
Heading into July, the Red Sox were becoming something of an afterthought in the American League playoff race. A 14-game winning streak has the Red Sox right back in the mix and currently occupy the third AL wild-card berth at 51–48. The postseason is now a legitimate possibility for Boston, but will their recent good run be enough to convince Craig Breslow & Co. to get aggressive at the deadline? If so, the team will look to find some offensive upgrades, as their 407 runs scored are the fourth-fewest in the AL, and the team’s .709 OPS is 10th-lowest in MLB.
Chicago White Sox
Key question: Can the team upgrade its pitching staff without tearing down the farm?
The White Sox are another big surprise thus far into the season, but they’ll need to upgrade their starting pitching rotation if the team truly intends to stick around in October. Chicago has had excellent production from Davis Martin and Sean Burke, and Anthony Kay has been serviceable. However, the team needs more if it wants to succeed in the postseason. Doing so without decimating its farm system will be a challenge, but the need for an additional arm is apparent.
Cleveland Guardians
Key question: Can the Guardians land a slugger at the deadline?
In a weak American League, the postseason is very much within reach for the Guardians. Two areas of need stand out for Cleveland: the bullpen and a power hitter. The Guardians have hit 94 home runs this year, tied with the Red Sox for the third-fewest in MLB. The return of Jose Ramirez should help in that regard, but adding some more pop to the lineup could make a big difference as the team fights for its place in the postseason. The Guardians don’t have a single player with more than 11 home runs on the year, and only the Padres have fewer runs scored (386) than Cleveland’s 391.
Texas Rangers
Key question: Will the Rangers be buyers?
The Rangers are just a half-game back in the AL West, but is that enough to warrant any big moves at the trade deadline? Texas has a thin farm system, so they’ll be reluctant to let go of any of their best prospects. If the Rangers don’t believe they have a chance to make a deep run in October, they’d be better off standing pat at the deadline, even if they’re leading the division come the end of the month. The next couple of weeks will be crucial for Texas to give an honest assessment of its roster and its chances of competing for a championship.
Seattle Mariners
Key question: What can Seattle get in return for one of their starters?
The Mariners need to improve their offense. Only the Guardians have scored fewer runs than Seattle in the American League. With plenty of talent in the starting rotation, Luis Castillo may be the odd man out and could be dangled as a trade piece at the deadline. The Mariners made an impressive run to the ALCS last season, but with Cal Raleigh struggling, they’ve lacked the same potent offense that helped carry them in ‘25. Adding a right-handed bat at the deadline will be important for Seattle, and they’ll hope that Castillo (or perhaps Bryan Woo or George Kirby) can net them a good one.
Atlanta Braves
Key question: Can the Braves shake off their summer slump?
The Braves started hot this season but have cooled off considerably throughout June and July. Their once comfortable lead in the NL East has shriveled to a mere three-game cushion over the Phillies. It wouldn’t be much of a surprise to see Atlanta take a big swing at the trade deadline, but whether they’ll aim to improve the lineup by adding a right-handed bat or go after a starting pitcher to help navigate their injury crisis in the rotation––or potentially both—remains to be seen.
Philadelphia Phillies
Key question: Can the Phillies address all their needs by the trade deadline?
The Phillies’ resurgence has them chomping at the heels of the Braves in the NL East, but there are some areas of the roster they’ll need to address if they hope to contend for a World Series. The bullpen needs an upgrade after Brad Keller suffered a season-ending UCL tear, and a back-end starting pitcher to round out the rotation is another move they’ll likely be mulling. Additionally, the team hasn’t gotten great production out of its current crop of outfielders, with the exception of Brandon Marsh, so it’s possible they’ll look for an upgrade there, too.
Miami Marlins
Key question: Will the Marlins make an aggressive push for the postseason?
The Marlins are still hanging around in the wild-card race despite entering the season with low external expectations and currently owning a seven-game losing streak, which means the front office has to decide whether or not to make some aggressive moves at the trade deadline to make a postseason push. There are certainly areas on the roster that could stand to be upgraded––third base comes to mind—but only time will tell whether Miami feels confident enough about its chances to compete for the postseason to make a significant dip into their farm system at this year’s deadline.
Milwaukee Brewers
Key question: How will the Brewers respond to Brandon Woodruff’s season-ending injury?
The Brewers’ pitching has carried them for much of the season, but the season-ending injury to Brandon Woodruff may force the team to reconsider its options at the trade deadline. It’s possible Milwaukee will roll the dice with its current ensemble of starters, but they may look to track down an experienced starter, perhaps one who has pitched meaningful October innings, to stabilize the group ahead of a potential push for the World Series.
Chicago Cubs
Key question: How much will the Cubs give up to improve their pitching?
The Cubs are expected to be in the market for some pitching upgrades at the trade deadline, both in the starting rotation as well as the bullpen. Just how much they’re willing to give up to do acquire those assets isn’t clear, however. Chicago doesn’t have the most formidable farm system at present, though they do have three prospects within MLB Pipeline’s Top 100––Jefferson Rojas, Josiah Hartshorn and Jaxon Wiggins.
St. Louis Cardinals
Key question: Will the Cardinals reverse course and make a postseason push?
A year ago, the Cardinals were one of the biggest sellers at the MLB trade deadline, and gave every indication last offseason that they were building for the long term. But the tables may have turned. At 51–48, St. Louis is tied with the Marlins and Pirates for the NL’s final wild-card berth. Is that enough to convince the front office to try to make a big splash? Starting pitching is a clear need for the Cardinals, but whether the front office is willing to commit to making an aggressive postseason push is still up in the air.
Pittsburgh Pirates
Key question: How much will it cost the Pirates to pursue a top bullpen arm?
The Pirates are pushing for their first postseason berth since 2015. Pittsburgh’s bullpen has been lackluster this season, however, and it’s an area they’ll likely try to address soon. Getting a reliable late-innings option out of the bullpen would help the Pirates tremendously as they vie for a wild-card spot, but if the market for relief pitching skyrockets at the trade deadline, as it often does, will they still be buyers?
Los Angeles Dodgers
Key question: Does Shohei Ohtani’s injury impact the Dodgers’ trade deadline plans?
Shohei Ohtani is taking a hiatus from pitching as he looks to recover from a lingering knee injury. The Dodgers don’t have a timeline for him to return to the mound, and they’ll have a couple of weeks to decide whether his absence on the mound will impact their plans at the trade deadline. With Tyler Glasnow and Blake Snell expected to return from injury during the second half of the season, L.A. may opt to hold pat, but with a three-peat on the line, they may look to add an insurance arm to the mix.
Arizona Diamondbacks
Key question: Will the D-Backs play well enough this month to impress GM Mike Hazen?
The Diamondbacks’ general manager said earlier this month that he wants to be a buyer at the trade deadline, and challenged his team to convince him to do so with their play. At present, Arizona sits at 51–48, just a half-game out of the final wild-card spot in the National League—though that spot is occupied by three teams in the Cardinals, Marlins and Pirates. How the Diamondbacks perform over the next couple of weeks could dramatically impact the organization’s plans at the deadline.
