5 Teams Who Will Regret Deadline Decisions the Most

Hayes is having the worst offensive season of his career, but his defense is value enough for his contract. His 16 OAA rank him in the 99th percentile of defenders in MLB, and the gap between him and the third baseman with the second-most (Maikel Garcia) is 9 OAA behind him…Garcia has 7 total OAA. Adding on the fact that Hayes was traded to Pittsburgh’s division rival in Cincinnati, it’s likely at this point to presume trading Hayes will haunt the Pirates for some time.

2. Los Angeles Angels

• LHP Jake Eder and 1B Sam Brown to WSH for LHP Andrew Chafin and RHP Luis García

• OF Wilberson De Pena and Future Considerations to NYY for 3B Oswald Peraza

The Los Angeles Angels continue to baffle their fanbase and universal baseball fans with their lack of dedication to rebuilding. They sat 9 games back in the American League West division and 4.5 back of the last AL Wild Card spot going into the trade deadline, and they don’t seem to be challenging for a playoff position going into the latter portion of the season.

Like the Pirates, the Angels had a confusing deadline as they chose not to sell off their veterans whose contracts expire at the end of the season. Tyler Anderson, Kenley Jansen, Kyle Hendricks, and Luis Rengifo all hold some extent of positive trade value and the Angels needed to move on from these aging players as they aren’t going to be competitive this year.

Taylor Ward was another obvious trade chip, and he’s under control through 2026. He’s felt like a candidate to be moved for years now, but the Angels stood pat. Again.

The team with the longest current postseason drought in baseball continues to try and find a solution to this by buying veterans and notably has signed some of the worst contracts in baseball history in recent years. The Angels’ farm system has strong pieces, and heading in to the 2025 season it was ranked by MLB.com as the league’s worst farm system. They remain uncompetitive on the minor or major-league level, and their decision to buy at this year’s deadline is confusing for several reasons.

Relievers Andrew Chafin and Luis García are good arms to strengthen the league’s worst bullpen by fWAR heading into the trade deadline (-0.9 cumulative fWAR), but their concerns need to be on future seasons and not to build a contending team in 2025. GM Perry Minasian has successfully thwarted yet another potential successful trade deadline where the Angels could work on being contenders in the future. 2025 is simply not the year for them to sell off prospects from an already-weak farm system to build for what will very likely result in another year of October-less baseball in Anaheim.

3. Atlanta Braves

• Future considerations to STL for RHP Erick Fedde + cash

• Cash to NYY for RHP Carlos Carrasco

• RHP Austin Smith to COL for RHP Tyler Kinley

• RHP Rafael Montero to DET for SS Jim Jarvis

The Atlanta Braves sat just 2 games above the 44-64 Washington Nationals for last place in the National League East Division heading into this year’s trade deadline. While the team is severely underperforming expectations due to injuries to star players like Spencer Strider and Ronald Acuña Jr. and a PED suspension to free agent signing Jurickson Profar, they had a confusing deadline.

Before the deadline, Atlanta’s starting pitchers had a 4.21 combined ERA on the season, good enough for 19th-best in MLB. Their rotation has been mired with injuries all season long, and they basically have a full rotation of strong starters all on the IL; Grant Holmes, Spencer Schwellenbach, Chris Sale, AJ Smith-Shawver, and Reynaldo López are all on the Injured List as of August 9 and the Braves simply sought to get some arms to fill innings.

The starters they brought in (Carrasco, Fedde) have had relatively poor seasons and will be joining a team with hardly any hopes for postseason baseball in 2025. Fedde was even DFA’d by the Cardinals earlier this month. While these moves do address a need for the team this season, Braves fans must be confused by the lack of moves to bolster the team over the coming seasons. Whether this is an indicator that Atlanta simply believes that all their arms will be healthy in 2026 and beyond or that they’re looking for inning-eaters, it’s underwhelming to say the least.

The addition of Kinley is basically moot because the team also traded away fellow reliever Montero to the Detroit Tigers. Montero posted a 5.50 ERA across 36 games with the Braves this season, Kinley posted a 5.66 ERA in 49 games for the Rockies. Kinley at least has a club option for 2026 that Atlanta might pick up, but the addition isn’t anything too special. He’s pitched the last five-and-a-half years of his career in Colorado so maybe the shift out of Denver’s pitcher purgatory benefits the Braves next year.

4. Boston Red Sox

• OF James Tibbs III and OF Zach Ehrhard to LAD for RHP Dustin May

• 1B Blaze Jordan to STL for LHP Steven Matz

May and Matz are good additions to a pitching staff that appears to be headed for October baseball in 2025, but the problem with Boston’s deadline is not necessarily who they got…but rather who they didn’t get.

The Boston Red Sox are always linked to prominent free agents and trade targets, and they’ve been part of some of the biggest trades in recent memory: trading Rafael Devers to the Giants, acquiring Garrett Crochet from the White Sox, trading Mookie Betts to the Dodgers. However, the rumor mill had seriously linked the Sox to acquiring starters Joe Ryan from the Twins and Sandy Alcántara from the Marlins.

Ryan was reportedly on his way to the Red Sox in a trade as the deadline’s last minutes dwindled away, but Red Sox insider Chris Cotillo put the rumours to sleep. The Red Sox had the 15th-best ERA among starters heading into the deadline, and having twin aces in Crochet and Ryan would have been a real difference maker in a playoff series.

May is having a down season thus far and got shelled in his first outing in Boston. Matz is a pending unrestricted free agent following this season but has been pitching very strong out of St. Louis’ bullpen in 2025. Alcántara would’ve been a good arm to add to a rotation that needs strong starting pitching over many innings of work, but the Red Sox weren’t able to get it done.

In the process of making these meager improvements to their roster, Boston traded away their No. 5 prospect in Tibbs, the main prospect return in their trade of Devers earlier this season. However these moves serve to benefit the Red Sox as the season winds to a close, we can only wonder how much they would’ve done with Ryan and/or Alcántara on their team.

5. Chicago Cubs

• SS Ronny Cruz and LF Christian Franklin to WSH for RHP Michael Soroka

• SS Wilfri De La Cruz to BAL for RHP Andrew Kittredge

• RHP Sam Armstrong and RHP Ryan Gallagher to MIN for INF/OF Willi Castro

• OF Ivan Brethowr to PIT for LHP Taylor Rogers

The Chicago Cubs made some moves at the deadline to bolster their bullpen with right-handed arms (Soroka, Kittredge) and left-hander Rogers from non-competitive teams but didn’t add any strong hitters. It’s worth mentioning that Chicago had the 13th-best bullpen ERA in baseball (3.86) coming into the trade deadline but had the league’s best offensive fWAR as a team (24.2) so their priorities were to improve the pitching staff.

Soroka was a good-intentions add, but he’s currently on the injured list with an ominous sounding shoulder injury. He had experienced decreased velocity prior to the trade and made it just two innings into his first start with the Cubs before being pulled with an injury.

However, the Cubs are in a situation where they are competing for the league’s best record, and they were tied to many prominent free agents. It can’t be a surprise to anyone to say that it’s a little disappointing that they didn’t go after any big names. They’ll have to hope these bullpen arms will make a big difference come October. Kittredge has already thrown an immaculate inning since joining the Cubs, so maybe they didn’t need to hunt a top trade piece.

Chicago held the National League’s top Wild Card spot on July 31st, and they were expected to make big splashes at the deadline to bolster their young roster with grizzled veterans with playoff experience. The only offensive change that they made was acquiring utilityman Willi Castro from the Minnesota Twins. Castro was an All-Star last season for the Minnesota Twins and this season he’s slashing .245/.335/.407, around the same as his line from 2024, but his fWAR has plummeted from 3.0 to 1.1.

His fielding has gone from around league average last season (0 OAA) to well below average in 2025 (-6 OAA). Castro is a free agent after this season, and the Cubs are going to have to hope he can bring something to the table come October. Their bullpen got a lot stronger and they added a utility man to their already-strong lineup. But in their seven games since the trade deadline, they have a team wRC+ of just 67. Nothing to panic about just yet, but if the postseason doesn’t bear great success fans will be wondering why more wasn’t done at this year’s trade deadline.

Closing Thoughts

These five teams may not have set themselves up for the most success possible as the season’s last legs are just beyond the horizon, and while there are winners at every deadline there absolutely are losers.

Only one team can hoist the Commissioner’s Trophy at the end of the year, and the trade deadline is almost always a crucial aspect to a team’s road to doing so. Time will tell how these teams fared, but it’s fair to say now that they didn’t hit a home run this time around.