Every day, Pinstripe Alley offers updates on what the Yankees’ top American League opponents are up to through the Rivalry Roundup. The AL East is well-trodden ground there, but with the Trade Deadline behind us, we’re going to take a peek around MLB as a whole and check in with each of the other five divisions. Who’s surprising? Who’s underwhelming? Who’s simply mediocre at the moment? Read on and find out.
First Place: Milwaukee Brewers (70-43)
Top Position Player: Brice Turang (4.1 fWAR)
Top Pitcher: Jacob Misiorowski (5.0 fWAR)
Not to editorialize too much in this space, but I believe the Brewers blew it.
It is a fact that Milwaukee has the league’s best record at time of writing. It is also a fact that they had the league’s best record in 2025, and all it got them was a sweep at the hands of the Dodgers in the NLCS. The one player who it felt Milwaukee could snag at this deadline to put them at close to level footing with the Dodgers, Tarik Skubal, is going to Los Angeles for somewhat less than a king’s ransom. The Brewers added only Dustin May and JoJo Romero from the Cardinals, Antonio Senzatela from the Rockies, and additional bullpen and catching depth from Cleveland in a marginal move most missed.
Over the past decade, Milwaukee has demonstrated that they have essentially solved the regular season. The postseason has proved a harder beast to tame, winning just two playoff series and falling to to LA in both the 2018 and 2025 NLCS. The franchise has never won a World Series and it’s been 44 years since they were even there, back when they were an AL team. The Brewers have tons of very good players, but lack the boundless star power of the Dodgers, star power which they used to absolutely bully the Crew up and down the field in October. Furthermore, with labor tensions on the rise and a potential work stoppage in the offing when winter comes, shouldn’t there be more urgency to go more all-in for the rest of this season?
The Brewers are not the only team guilty of being overly safe. But they’ve done all the hard work, constructing a formidable platform on which a superstar like Skubal would have perfectly fit, were they only willing to pull the trigger. Instead, they once again got gun-shy, putting together a good offer but not one that blew the Tigers away. The far tougher path awaits. I wish them luck.
Second Place: Chicago Cubs (65-49)
Top Position Player: Pete Crow-Armstrong (7.3 fWAR)
Top Pitcher: Ben Brown (2.0 fWAR)
The Cubs were busy, busy bees at the deadline; and they had to be. Chicago remains comfortably afloat in the first Wild Card spot despite suffering through terrible injury luck, particularly in the rotation. So they went to work rebuilding their staff on the fly, and I think they did fairly well for themselves given a somewhat limited set of options.
First, the Jed Hoyer-led front office made a pair of deals with Toronto, a team which managed a shrewd buy/sell balancing act. Gone was DFA’d veteran Jameson Taillon, and in his place came Kevin Gausman. Gausman has not been ace material this year, and his walk rate has shot up, but it is far better to have him than to not. The Cubs continued with more of a lottery ticket by adding lefty Braxton Garrett, bolstered their bullpen with the Angels’ Ryan Zeferjahn, then concluded by bringing along old friend Clay Holmes (alongside Tyrone Taylor) from the aggressively-selling Mets.
In the aftermath, as MLB.com’s Mike Petriello noted on Bluesky, the Cubs now have a great collection of depth options in their rotation to go along with an offense which boasts NL MVP favorite Pete Crow-Armstrong at the top of the lineup. At the same time, none of their pitchers are the kind of guy you’d be pumped to see start the first game of a future playoff series. The Braves have Chris Sale; the Brewers boast Jacob Misiorowski; the Dodgers now have Skubal in addition to Yoshinobu Yamamoto.
Maybe something with Gausman clicks down the stretch and he becomes the ace they need, but otherwise, it’s a lot of good-but-not-great arms. After Skubal came off the board, that’s essentially all that the market could provide. Credit to the Cubs for working within those confines to upgrade their roster as much as they could.
Third Place: Pittsburgh Pirates (57-58)
Top Position Player: Brandon Lowe (3.1 fWAR)
Top Pitcher: Paul Skenes (3.6 fWAR)
In a departure from past seasons, the Pirates are both alive in the playoff hunt and adding to their roster at the deadline, albeit exclusively in the bullpen. After picking up Camilo Doval from the Yankees as a potential reclamation project—a project which the Yankees themselves attempted and failed to complete—Pittsburgh got more serious, trading for Luke Weaver from the Mets and Kirby Yates from the Angels. Those veterans (particularly Weaver) should give the Bucs more stability in their back-end as they look to end the longest active playoff drought in the Senior Circuit.
The warning signs for this team are everywhere, however. Paul Skenes has not looked like the best young pitcher in baseball this season, as a dip in velocity has allowed teams to get the jump on him. Ryan O’Hearn, one of their most reliable veteran hitters, suffered a nasty injury and will be out for another six weeks at minimum. He joins rookie Konnor Griffin on the IL; the shortstop may be back in time for the beginning of September, but it’s hard to know if Pittsburgh will be able to keep pace with a competitive NL in the meantime.
Still, the Bucs didn’t luck into being the second-highest scoring offense in the league most of the way through the season. They have a good collection of youth and experience in their lineup even despite the recent injuries, and have a fleet of young right-handed starters (including Skenes, who could always turn the corner) at their disposal. Too often, the Pirates have said “never.” It’s nice to see them at least say “maybe.”
Fourth Place: St. Louis Cardinals (56-58)
Top Position Player: JJ Wetherholt (4.0 fWAR)
Top Pitcher: Dustin May (2.6 fWAR) Andre Pallante (2.0 fWAR)
The Cardinals shoved the Yankees into a locker on Monday night, and if that result had come before the deadline rather than a few hours after, it’s easy to wonder if the front office might have been tempted to take a different approach. As it happens, though, St. Louis decided to assume a modest sell position, dealing May and Romero to Milwaukee as previously mentioned while sending Team Japan icon Lars Nootbaar to the Diamondbacks right before the closing bell.
It was the right time to move off all of those guys; they’re talented but flawed players who didn’t figure to be part of the next competitive Redbirds squad. St. Louis has struggled to begin the second half, and their youth movement is still a work in progress. Make no mistake: the now-extended JJ Wetherholt is agreat player. So is Jordan Walker. Alec Burleson thumped three homers in the Bronx on Monday night; he’s pretty good too. But the pitching staff isn’t there yet, and neither is the rest of their lineup.
If nothing else, though, St. Louis has demonstrated they’re a team you can’t afford to mess with. To the other teams in this division, take heed: if you have the opportunity to put the Cardinals away, you need to do it, or else you may just see them in the playoffs.
Last Place: Cincinnati Reds (54-58)
Top Position Player: Elly De La Cruz (4.1 fWAR)
Top Pitcher: Chase Burns (3.3 fWAR)
With Adley Rutschman and Liam Hicks taken off the table by division rivals, it appeared the Yankees’ only realistic path to an upgrade at catcher was Tyler Stephenson of the Reds. Even then, Stephenson’s defensive proclivities threatened to make it more of a lateral move, even with Austin Wells’ horrible 2026 season. Ultimately, Brian Cashman opted not to pull the trigger, and Cincinnati got no takers for their pending free agent catcher.
They got no takers for just about everyone, as it turned out—only flipping lefty first baseman Nathaniel Lowe to the cross-state rival Guardians and shipping Caleb Ferguson to the Cardinals just before the music stopped. It was fairly bleak for Reds fans. Cincy just didn’t have a lot of trade pieces worth getting excited about—that doesn’t mean there aren’t reasons to tune in to watch them.
Chase Burns continues to rise as a young ace for an exciting young pitching staff which continues to hold a lot of promise for the years ahead. Elly De La Cruz remains one of the most electric players in baseball, even though we may not see him steal 67 bases like he did in 2024 again. Sal Stewart is already a formidable heart-of-the-order bat for the Redlegs as a rookie; he could be there for a long time. Cincinnati is a terribly flawed squad, it’s true. But they don’t lack for hope.
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