usatoday
The Milwaukee Brewers' World Series triumph has officially shifted the baseball world into offseason mode, leaving Pittsburgh Pirates general manager Ben Cherington with a lengthy to-do list as he aims to guide the franchise back to the playoffs for the first time since 2015. Complicating matters is the looming uncertainty surrounding the sport's next collective bargaining agreement, with players and owners reportedly at odds over its structure. The possibility of canceled games—or even a lost season—in 2027 could significantly alter how Cherington and other executives approach their winter planning.
Can Paul Skenes Be Fixed?
For most pitchers, a 10-11 record with a 3.82 ERA and 200 strikeouts over 32 starts would be considered a strong season. But for Paul Skenes, the 24-year-old ace who won the Cy Young Award in 2025, those numbers represent a significant step back. His ERA jumped nearly two full runs from 1.97 the previous year, and his Fangraphs WAR fell from 6.5 to 4.2. Particularly troubling was a nine-start stretch from May 17 to July 1 in which the Pirates lost every game he pitched. The team ultimately missed the playoffs by six games, though some observers may overstate how much Skenes alone could have closed that gap—WAR numbers suggest six games is a massive swing for any single player.
Still, Skenes remains the club's best player, and any hope of ending the postseason drought starts with him. Manager Don Kelly and pitching coach Bill Murphy must find solutions, especially given the decision to part ways with Oscar Marin—the pitching coach with whom Skenes had the most success—after the 2025 season. That move, followed by Skenes' decline, has raised eyebrows and increased pressure on the new staff to prove the transition was not a mistake.
Will Brandon Lowe Return?
Veteran second baseman Brandon Lowe delivered one of the most powerful seasons in recent Pirates history, slugging 35 home runs and 29 doubles after being acquired from the Tampa Bay Rays last December. Now a free agent for the first time after exhausting his arbitration eligibility, the 32-year-old presents Cherington with a stark choice: pay the substantial salary he will command on the open market or let the team's best offensive player walk for nothing.
Each path carries risk. Losing Lowe would weaken the lineup immediately, but a long-term extension for a player past his 30th birthday could lead to diminishing returns. The Pirates do have internal power options emerging: rookie outfielder Esmerlyn Valdez hit 17 homers in 72 games in 2026 (a 38-homer pace over 162 games), and 25-year-old catcher Rafael Flores Jr. slugged 11 in 47 games (projecting to 25-30 over a full season, though he is unlikely to play every day due to his position). Fan backlash would be swift and severe if Lowe departs, and given the team's modest payrolls under Cherington, many will argue there is ample money to retain a proven commodity. The question is whether investing heavily in one aging player is wiser than spreading that cash across multiple bets—if notoriously frugal owner Bob Nutting approves a payroll increase.
Can the Bullpen Improve?
Pittsburgh's bullpen blew 26 saves in 2026, the 11th-highest total in baseball and a primary reason the team fell short of the postseason despite ranking fifth in runs scored. Most of the damage occurred early in the year, but solutions began to emerge by season's end. Yohan Ramirez (2.86 ERA), Mason Montgomery (2.88), and Gregory Soto (3.63) all posted solid numbers, while trade-deadline acquisition Luke Weaver, after a rocky start, allowed no runs in six of his final seven appearances.
The bullpen has been a persistent problem throughout Cherington's tenure. That he largely fixed it by the end of the year is encouraging, but fans are justified in believing he should have acted more aggressively sooner—and in worrying about similar missteps this offseason. The pressure is now on to have this group ready to compete from opening day in 2027.
Originally reported by usatoday.