What Pirates Can Learn From the Two World Series Rosters

PITTSBURGH — The Pittsburgh Pirates weren't close to making the postseason, and even further from reaching the World Series, but there is still hope they can do so in the future.

The 2026 World Series pits the Milwaukee Brewers against the Tampa Bay Rays in a battle between baseball's two best teams.

Milwaukee is Pittsburgh's National League Central Division rival and won its first pennant since 1982, while Tampa Bay won its third pennant since 2008.

Both teams are looking for their first World Series in team history and are showing that small-market ballclubs can achieve glory in MLB, something the Pirates can't use as a hindrance any longer.

Be Bold and Make the Right Trades

Milwaukee and Tampa Bay are both in the World Series for the trades they have made in recent history.

Most of each team is made up of players acquired in trades, with the Brewers having 15 and the Rays having 17, making up the majority of their World Series rosters.

Milwaukee Brewers Players Acquired by Trade

Tampa Bay Rays Players Acquired By Trade

The Brewers have the vast majority of their bullpen from trades, plus starters in catcher William Contreras, first baseman Jake Bauers and designated hitter Christian Yelich.

Tampa Bay landed some top players recently, starting pitcher Freddy Peralta and catcher Liam Hicks at this trade deadline.

One major thing that both teams have done well is that their traded players have come across the past seven and eight seasons, showing how long it takes to build great rosters.

Tampa Bay traded for third baseman Junior Caminero and starting pitcher Drew Rasmussen in 2021 and designated hitter Yandy Díaz in 2018.

Milwaukee traded for Contreras back in 2022 and Yelich in 2018, while making more shrewd trades recently.

Peralta is an interesting World Series connection, as the Brewers traded him to the New York Mets ahead of his final year before free agency.

The Mets had a terrible season and traded him at the deadline to the Rays, who got him back to what he does best and he has played a role in their World Series run.

Another tie is Brewers first baseman Jake Bauers, whom the Rays traded to the Cleveland Indians back in 2018, the same trade that landed them Díaz, and Bauers played for the Cincinnati Reds and New York Yankees before landing with his current team.

Both teams have made savvy and smart trades, while acting unafraid to make mistakes and go for big-time additions, especially when they are competing.

Milwaukee and Tampa Bay have been quite successful over the past two decades, and this has allowed them to add strong players, keep them and take advantage of their time with the team.

The Pirates have struggled with making the bold trades they need to, which would get them over the edge and make them a winner once again.

Pittsburgh did better with trades over this past season, adding second baseman Brandon Lowe, outfielder Jake Mangum and left-handed relief pitcher Mason Montgomery from the Rays, while parting with right-handed starting pitcher Mike Burrows to the Houston Astros.

The Pirates also added two solid right-handed relief pitchers, Luke Weaver from the Mets and Lake Bachar from the Miami Marlins, at the trade deadline.

Pirates general manager Ben Cherington excelled with his trade to the Rays, but it shows how important building a strong team beforehand is, as the Rays are still in the postseason.

The Pirates just had their first winning season since 2018 and still haven't made the postseason since 2015, the second-longest streak in MLB.

It's time for the front office to make those difficult choices and make the Pirates the best team they can be in 2027, getting them back into the playoffs.

Build a Strong Bullpen From the Outset

The Pirates didn't have a strong bullpen in 2026, which played a big role in them not having the season they wanted.

Pittsburgh never made the right moves from the outset with the bullpen, and when some of their better pitchers regressed, they were left scrambling to fix it, not finding a solution until the trade deadline.

Both the Rays and Brewers have great bullpens, posting some of the best numbers in baseball this season.

Milwaukee has the likes of Trevor Megill, Abner Uribe, Aaron Ashby, Chad Patrick and DL Hall as key fixtures in its bullpen, and Tampa Bay has top relief pitchers in Kevin Kelly, Bryan Baker and Cam Booser.

Both teams have relied on their bullpen in the postseason, with the Brewers posting a 1.33 ERA and the Rays posting a 3.60 ERA.

The Pirates have strong options in their bullpen for next season: Weaver as the setup man and Montgomery as the shutdown closer, plus Bachar, Yohan Ramírez and Carmen Mlodzinski as middle relief options.

Pittsburgh should target high-leverage arms in free agency and by trade, doing anything they can to not make the same mistake they did last offseason and make this a championship-caliber bullpen.