LAS VEGAS — The Pittsburgh Pirates have faced disadvantages as a small-market team, but those excuses are becoming less worthy by the day.

The 2026 World Series featured two small-market teams, with the Milwaukee Brewers defeating the Tampa Bay Rays in five games for their first championship in franchise history.

Pittsburgh finished 82-80 in 2026, clinching just their first winning season since 2018 and just the fifth in the past 34 seasons, while last making the postseason in 2015 and not winning a playoff series since the 1979 World Series.

Pirates general manager Ben Cherington enters his eighth season in the role, and he knows the pressure to finally deliver winning baseball in 2027 and beyond.

World Series Featuring Two Small-Market Teams

The General Managers' Meetings at the ARIA Resort and Casino gave important front office members in all 30 MLB teams a chance to come together and start building communication on what moves they all want to make.

Cherington has a Pirates team that could clinch a postseason spot next season, but crucial maneuvering to build the best roster, especially with an impending lockout coming on Dec. 1, which ends all MLB transactions, makes it more difficult than in recent seasons.

The World Series between the Brewers and Rays featured the 19th-lowest and 28th-lowest payrolls, respectively, with the Pirates in the middle of that at 23rd overall.

Milwaukee and Tampa Bay didn't just fluke into the postseason; the two teams were the best in their respective leagues and have been successful for the last decade.

Cherington noticed how awesome it was to watch both teams play, but also that the Pirates aren't close to them right now and need to improve to get there.

"Yeah, yeah. I don't think we needed that necessarily to feel that way, but sure, of course, like it's a lot," Cherington said.

"First of all, the World Series was just a lot of fun to watch. You know, the style of baseball. It's just elite pitching, elite defense, athletic, fast. I mean, it's just a fun brand of game, brand of baseball to watch. I thought, and certainly that's by design, right?

"That's how those teams were built, and they've both done just exceptional work over a long period of time to get to that point. And and and it's if you think about those rosters, it's got a chance to be pretty sustainable. Like they're not either of those teams are going away.

"So what it means for us is just man, just keeps the bar really high. You know, we gotta, we made some progress this year, and then you watch the World Series, and it's very clear. Okay, we gotta be. Don't take anything for granted.

"I mean, there's, there's still significant gap between where we were and how those teams were playing at the end of October.

"We got to be laser-focused on how do we close that gap, and obviously, you know, just got to do it in a way that makes sense for the Pirates, and that's always going to be a little bit different than it would be for other teams."

Why Milwaukee Brewers Have Been Better Than Pirates

The Brewers were the best team in baseball in the regular season, going 103-59, and have been a model for small-market success in MLB.

Milwaukee has made the postseason in eight of the past nine seasons, winning the National League Central five times, including four straight years doing so.

It's a drastic difference from the Pirates' having the second-longest postseason drought in MLB, with only the Los Angeles Angels longer (2014).

The Brewers excel at almost everything, which includes playing great defensively, having a strong lineup, one through nine, and a fantastic pitching staff with an elite bullpen.

Cherington noted that it's more than just improving the roster to become the Brewers; it also means executing consistently in each game to get the best outcome.

"Well, we talked about pitching before and we were focused on the pitchers themselves, but there's a defensive element to run prevention that clearly the Brewers are succeeding in," Cherington said.

"Now we can't replicate that entirely. Obviously, trying to copy and paste it doesn't work, but there are still things we can do to be a better defensive team.

"You know, I think on the offensive side, you just look at the approach. Their hitters, they just, so disciplined. Whether that's pitches they're swinging at, or you know, willingness to use the whole field, or be really selfless in the at-bat and take the ground ball the other way when it's there, that kind of thing. It's, it's fun to watch, and I think we did that at times and won games that way, and probably got out of it at times, so you know, consistency of that approach.

"So I can keep going, but you know there are, there's the roster itself and making that better, and then there's also how we play on a day-to-day basis, and we definitely took a step forward in my, my opinion this year in terms of that consistency and our intensity, and there's still room to grow."

How Can Pirates Bridge Gap?

The Pirates did improve by 11 wins last season, but it was still short of their ultimate goal of postseason baseball.

Pittsburgh has a strong group returning, including a rotation with top, young arms, a lineup that went from the worst in MLB in 2025 to one of the top in 2026, and solid prospects that can help them build upon it.

The Pirates finished 7-6 against the Brewers, which included a series sweep at PNC Park before the All-Star break.

Pittsburgh is close to finally breaking through, but they must be more consistent across an entire campaign to get to where they want to be, something that Cherington learned this season.

"Yeah, I mean, we've swept other teams too. I mean, we're good enough to win games when we're playing really well and executing, and you got to do that for 162, and then you got to build a team that can do that through October, and that's different," Cherington said.

"So it goes back to that, right? It's a launch of baseball. It's beauty of baseball. I think is like this: the length of the season tells you what you are and exposes all the good things and also all the, you know little gaps that you got to fill, and we learn from that and get to go do something about it now."