One offseason regret already haunting each AL East team

Two weeks into the MLB season, the AL East does not look nearly as formidable as expected. Granted, the sample size is obviously small, and injuries have ravaged this division, but three of the teams are over .500, while only three other teams in the AL are over .500 in the American League as a whole. The AL East isn't quite as dominant as some anticipated, but it's still been the best division in the AL.

Offseason regrets have a lot to do with the early-season struggles for at least some of these teams. Let's dive into what each team might be regretting from the winter.

Baltimore Orioles: Not acquiring an ace

Pete Alonso has started slowly, but it's too early to say the Baltimore Orioles should regret signing him. One decision that's gone awry that was easy to forecast, though, was their inability to acquire an ace. Starting pitching was a major concern for the Orioles entering the offseason, and while they did address it, they didn't do enough.

The best starting pitchers they acquired were Shane Baz and Chris Bassitt, two solid options, but ones who lack ace pedigree. Baltimore could've spent money on a proven ace like Framber Valdez or Dylan Cease. They could have traded for one like Freddy Peralta.

Trevor Rogers and Kyle Bradish are two very talented pitchers, but neither is particularly durable, and they've combined to throw just over five postseason innings in their careers. Passing on a chance to add a proven ace has certainly played a part in their rotation being mediocre thus far, and could come back to haunt them in October (if they get to the postseason).

Boston Red Sox: Not adding power

It felt like the Boston Red Sox lacked power in 2025, particularly after trading Rafael Devers away. They then proceeded to let Alex Bregman, the player who ranked third on the team in home runs despite missing substantial time due to injury, walk in free agency, and replace him with Willson Contreras as their big bat.

No disrespect to Contreras, but he hit just two more home runs than Bregman last season despite racking up nearly 100 more plate appearances. Even if you want to argue that Contreras and Bregman are at the same level when it comes to producing runs and hitting for power, again, they didn't even have enough power with Bregman.

Now, the Red Sox have just 11 home runs, the fewest in the American League, and are only 19th in runs scored as a result. It's really hard to score runs consistently, particularly in October, when you can't hit for power. Stringing hits together against quality competition is really hard. Hitting home runs is how you score efficiently. Boston's inability to do that might cost them a chance at the postseason, and even if they get there, it's hard to take them seriously as contenders barring a major influx of power.

New York Yankees: Ignoring the bullpen

The New York Yankees made Cody Bellinger their offseason priority and bolstered their rotation depth by acquiring Ryan Weathers, but they practically ignored their bullpen. An argument can be made that their big bullpen addition was selecting Cade Winquest in the Rule 5 Draft, and Winquest was recently DFA'd by the team after not appearing in a single game.

I get that Brian Cashman did much of the heavy lifting for the 2026 bullpen at the 2025 trade deadline by acquiring the likes of David Bednar, Camilo Doval and Jake Bird. I also like Fernando Cruz and Tim Hill a lot. Depth in this 'pen is a major issue, though. I mean, they began their season with Winquest, Paul Blackburn and Ryan Yarbrough securing the final three spots of the bullpen. Winquest had no MLB experience, and both Blackburn and Yarbrough are long relievers that the Yankees should want no part of seeing in big spots.

The trade deadline is a popular time of year to upgrade in the bullpen, and I'm sure Cashman will do that, but in a division that gives you no margin for error (remember, the Yankees lost the AL East title by virtue of a tiebreaker), refusing to sign a single notable external reliever could cost the Yankees some games that they'll come to regret.

Tampa Bay Rays: The Brandon Lowe trade

I understand why the Tampa Bay Rays traded Brandon Lowe this offseason. Lowe is slated to hit free agency after the 2026 season, and it's unlikely that the small-market Rays would spend what it'd take to extend him. Getting assets for him before likely losing him for nothing is something that the Rays and other small-market teams like the Milwaukee Brewers have done very well over the years. The trade itself, though, looks fairly iffy.

First of all, Lowe is having a tremendous start to his season, launching six home runs and driving in 14 runs with an OPS over 1.000 in 14 games with the Pittsburgh Pirates. Lowe has double the home run total as Yandy Diaz and Junior Caminero, the leaders in Tampa Bay. The Rays could certainly use him.

Second, Lowe wasn't the only player they gave up. Jake Mangum hasn't hit much this season, but is a tremendous fourth outfielder option who offers high-end speed and defense. Mason Montgomery has a 7.11 ERA thus far, but a 3.19 FIP, suggesting he's gotten quite unlucky. He has 14 strikeouts in just 6.1 innings of work, flashing ridiculous stuff out of Pittsburgh's bullpen. The Rays could've used both of these guys, Montgomery in particular.

Third, the Rays haven't gotten any value out of this deal yet. Jacob Melton, the centerpiece of their return, is in Triple-A (and is hitting .175 with a .645 OPS), and Anderson Brito is in High-A. Even Mike Burrows, a player the Pirates traded in this three-team deal, is with the Houston Astros. He hasn't pitched great, but with Joe Boyle and Ryan Pepiot injured, the Rays could use him too.

Trading Lowe is fine, only if you get the right return. The Rays' return doesn't look great right now, and Lowe raking in Pittsburgh isn't helping either.

Toronto Blue Jays: Whiffing on big bats

The Toronto Blue Jays went to the World Series and then immediately fortified their rotation by signing Dylan Cease and Cody Ponce. Their rotation is a bit of a mess right now, but it isn't their fault that much of their Opening Day rotation, including Ponce, is hurt. They had a ton of depth in their rotation. Something that is their fault, though, is the construction of an offense that ranks 26th in runs scored.

Sure, injuries have impacted the lineup too, with guys like Anthony Santander, Addison Barger, Alejandro Kirk and even George Springer missing time, but even before the season started, the Jays felt like they needed more offensive firepower. They signed Kazuma Okamoto, but there's a reason that even after they signed him, they were in on stars like Kyle Tucker and Bo Bichette in free agency.

It's hard to get on the Jays for whiffing on Tucker and Bichette when they signed such massive deals with the Los Angeles Dodgers and New York Mets, respectively, and it's not as if either star has even played well thus far. With that being said, Okamoto hasn't hit much either, and it's hard to fully buy into this Jays lineup.

Vladimir Guerrero Jr. is elite, but who else in the lineup truly frightens you? Springer, even before his injury, was struggling following his random resurgence in 2025. The 2025 Jays had Bichette as a star complement to Guerrero. If Springer isn't his 2025 version, do the Jays have enough offense? So far, the answer has been no.

More MLB news and analysis:

Add us as a preferred source on Google

Follow