Insider Drops Bold Prediction On Pirates Playoff Outlook

With the reigning Cy Young pitcher and a boatload of new players joining the team, it may finally be time for the Pittsburgh Pirates to make the playoffs.

Everyone knows the story, this team hasn't made the playoffs since 2015. Time and time again they've finished last place and fail to make any moves at the trade deadline or in the offseason.

All of a sudden, things are beginning to change. While it's still far too early to tell how this Pirates team is actually going to perform, it's at least worth noting how many moves they've made to improve their roster.

As part of ESPN's bold MLB predictions for the 2026 season, Jorge Castillo dropped a bombshell that may take Pirates fans by storm. Pirates fans won't believe it until it actually happens, but they could be destined to make the playoffs.

Jorge Castillo Predicts Pirates Make The Playoffs

Pirates Don Kell — Aug 3, 2025; Denver, Colorado, USA; Pittsburgh Pirates manager Don Kelly (12) during the first inning against the Colorado Rockies at Coors Field. Mandatory Credit: Ron Chenoy-Imagn Images | Ron Chenoy-Imagn Images

"The Pirates have failed to land one of the top available hitters this winter after showing real interest in Kyle Schwarber and Josh Naylor among others, but they've still managed to greatly boost the lineup with first baseman/designated hitter Ryan O'Hearn and second baseman Brandon Lowe plus speedy outfielder Jake Mangum and heralded outfield prospect Jhostynxon Garcia onboard," Castillo said.

He continued, "Pittsburgh finished 12 games behind the 83-win Cincinnati Reds for the third Wild Card spot. Chances are 83 wins won't be enough to reach the postseason in 2026 so it'll take a huge jump for the Pirates to snap their postseason drought. But if the pitching staff continues where it left off -- the group posted the seventh-best ERA in baseball with Skenes compiling a 1.97 ERA and winning the NL Cy Young Award -- and the lineup additions play to their potential, the Pirates could make real noise."

Pirates Out To Make A Statement In 2026

Pirates Paul Skene — Sep 16, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates starting pitcher Paul Skenes (30) high-fives in the dugout after pitching the fourth inning against the Chicago Cubs at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

There are no guarantees the Pirates make the playoffs, far from it, but they've begun to put in the work that is needed from a playoff caliber team. The NL Central is going to be competitive, as always, but there's a world where the Milwaukee Brewers or Chicago Cubs regress and miss the playoffs entirely.

If there was ever a year for the Pirates to make some noise, it's this year. Castillo isn't saying this team is going to win the World Series, but seeing as the division had three playoff teams last year, there's no reason not to believe the Pirates couldn't sneak their way into a Wild Card spot.

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