The Milwaukee Brewers keep putting on the kind of October show the Pittsburgh Pirates have been trying to build toward.
On Saturday, Milwaukee’s bullpen turned a four-run hole into a 5-4 comeback win over the Tampa Bay Rays in Game 2 of the World Series. The Brewers’ relievers worked six scoreless innings, helped flip the game, and pushed Milwaukee to a 2-0 series lead. With that performance, the Brewers’ bullpen picked up its eighth win of the postseason, matching the record set by the 2015 Kansas City Royals.
For a Pirates club still sorting out its own late-inning picture, that kind of depth is hard to ignore.
Pittsburgh spent much of the 2026 season trying to stabilize its relief corps and made several deadline additions to do it. The group improved, but the bigger issue still hangs over the winter: the Pirates have pieces, not a proven October bullpen.
They have arms that can matter in games. They do not yet have the sort of trust network that carries a team through an extended postseason run.
To Pittsburgh’s credit, there was real progress in the second half of the season. Mason Montgomery locked down the ninth inning and put together 25 straight scoreless appearances before finally allowing a run in late September. Luke Weaver also gave the Pirates a steady right-handed setup option after arriving at the deadline.
The numbers backed up the improvement. According to MLB.com, Pittsburgh’s bullpen posted a 3.49 ERA after the trade deadline, compared to a 4.34 ERA before it.
Still, the list of questions got longer as the season moved on. Gregory Soto is headed for free agency after an uneven year.
Kirby Yates has retired. Camilo Doval, another deadline pickup, was designated for assignment in September after he couldn’t find his footing in Pittsburgh.
Weaver is still under contract, and the Pirates do have additional bullpen options in Yohan Ramírez, Lake Bachar and Carmen Mlodzinski. But a full bullpen card isn’t the same thing as a playoff-ready bullpen. October demands relievers a manager can lean on without hesitation.
That’s exactly what Milwaukee showed again Saturday. Logan Henderson gave up four runs in the first inning, and the Brewers didn’t need to panic or burn through their options. JoJo Romero, Dustin May, DL Hall, Abner Uribe and Aaron Ashby handled the final six innings without allowing a run, giving the offense time to complete the comeback.
That’s the gap Pittsburgh still has to close. The Pirates can feel good about Montgomery’s rise, but a contender can’t stop there.
What happens when he’s unavailable? What happens when the starter is gone by the third inning?
Who handles a one-run game in the sixth if Don Kelly needs a trusted arm immediately?
Those are the kinds of questions that get teams eliminated in October if they aren’t answered before then.
Pittsburgh already has an impressive young starting group led by Paul Skenes, Jared Jones, Bubba Chandler and Braxton Ashcraft. But even that kind of rotation can’t guarantee seven clean innings every night, especially against postseason-level lineups. Sooner or later, the bullpen has to hold the line.
The Brewers are proving that bullpen depth doesn’t happen by accident. It has to be built with intent.
The Pirates finished 82-80 in 2026, a step in the right direction without reaching the postseason. If 2027 is supposed to be the year they actually push into contention, Ben Cherington has a clear lesson sitting in front of him: it’s not enough to assemble a bullpen that can survive the summer. It has to be strong enough to survive October too.
In Other News...
Paul Skenes Is Taking On A Fight Pirates Fans Should Watch
Paul Skenes has been front and center in a labor fight that matters far beyond the mound at PNC Park. The Pirates ace sits on the MLB Players Association executive subcommittee, putting him in the room for the collective bargaining talks that will shape the sports next economic framework, and he has made clear he is against a proposed salary cap because of what it could mean for players now and down the line.
For Pittsburgh, it is a reminder that Skenes is not just the face of the rotation but also one of the most important voices in a debate with real consequences for small-market teams. Even with his own financial future still wide open, he has argued the issue is about protecting players across the league, and the outcome of these negotiations could influence how the Pirates, and everyone else, build their rosters in the years ahead. [Read more 🡒]
Pirates May Face A Painful Trade Choice To Keep Brandon Lowe
Brandon Lowe is set to hit free agency, and the Pirates have every reason to want him back after seeing what he can bring to the middle of a lineup. He has already said hed like to stay in Pittsburgh, which only adds to the appeal for a club trying to build around proven talent rather than keep cycling through short-term answers.
The problem is the price tag. Lowe is lined up for a deal that would push beyond what the Pirates are currently set up to spend, putting the front office in a bind as it tries to balance payroll with the rest of the roster. If Pittsburgh is serious about keeping him, the next move may have to come from somewhere else on the roster, and that is where the conversation gets uncomfortable. [Read more 🡒]
Pirates Could Make One Telling Move If Brandon Lowe Leaves
Brandon Lowes future is already shaping up as a question for after the 2026 season, and that kind of looming free-agent decision tends to send front offices and outside analysts into roster-spot mode. For the Pirates, the conversation has centered on what they might do if Lowe departs, with the infield picture suddenly needing another answer and a potential opening for a more aggressive move on the market.
One Bleacher Report take has linked Pittsburgh to Jazz Chisholm Jr., who spent 2026 with the New York Yankees and would be one of the more recognizable names available if he reaches free agency. The idea is simple enough for a club looking to stay flexible: replace one high-profile infielder with another on a short-term deal, then see where the fit goes from there. For now, though, it remains a projection rather than a plan, and the real intrigue is whether the Pirates would be willing to make that kind of swing if the opportunity actually materializes. [Read more 🡒]